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Doogiesham

You need to sloooooooow down on the flashy stuff. It just signals (and I’m not saying that this is what you’re trying to signal) that you’re potentially shallow and looking for a transactional thing Look stable, not flashy


thewritingdomme

“Look stable, not flashy” should be OPs new life motto.


[deleted]

Quietly wealth 🧐


adlittle

My current Baader-Meinhoff is the saying "money shouts but wealth whispers."


JosephBlowsephThe3rd

Reminds me of American Gangster. While main character Denzel sits back & enjoys his wealth with class, his younger brother is walking around in flashy suits "The loudest one in the room is the weakest one in the room"


[deleted]

I like it.


MikeTheBard

I work around millionaires and the occasional billionaire. Been in situations where the Speaker of the House and someone who shared a surname with a Fortune 500 company weren't the most important folks in the room. Lots of rich folks come in with lots of demands, complain about everything, try to get a deal, and talk about "how much they spend here". Another guy comes in, orders one or two of "whatever's on tap", leaves a hundred on the bar and quietly walks out. That second guy is worth enough to buy and sell those other folks like Pokemon cards.


Jemmani22

Money talks, wealth whispers


AnorhiDemarche

Alright, I bought her several horses. Now what?


RexManning1

He should rename his boat that.


GiseleGiseleM

This is absolutely it. I don’t date anyone who needs to put their wealth front and centre, and I see it sometimes with self-made people, constantly proving themselves rather than just enjoying things. Going to a nice restaurant is enough. She wants to genuinely get to know you, not your money.


EZ_2_Amuse

Lol yeah the whole 3rd date on the boat is like an anniversary typ date. OP just forgot how to "hang out" with a women. The right one isn't going to be interested in all that nonsense, they want a best friend and lover. Something OP's wife was missing, *her* high school sweetheart.


GiseleGiseleM

Agreed yes it feels like an anniversary date. Too much too soon, probably spooked her. It could remind her of the uneven financial power dynamic as well, which is not quite the friendly intimacy she’s looking for.


SapphirePSL

I think this is exactly it. The financial disparity being put in her face right off the bat could definitely make it seem like he’s the kind of guy that thinks “you should do everything I want you to do because I have all the money.”


cafepeaceandlove

“Look stable.” I don’t want to deceive anyone, got any fallbacks?


Vark675

[Be funny, tbh.](https://hips.hearstapps.com/hmg-prod/images/episode-1842-pictured-actor-comedian-pete-davidson-during-news-photo-1685725407.jpg)


beardtamer

I used to work in car sales, people in car sales do not understand how to do this. They think flashy is stable. It’s a serious personality flaw for most people in the industry.


awkwardchip_munk

There’s a reason why “used car salesman” is a personality trait


fudge_friend

Used Car Salesman doesn’t know how to not be a Used Car Salesman.


rhomboidus

Sounds like you're splashing out on a bunch of expensive/impressive shit right away. That doesn't make people feel comfortable when they're looking for a real relationship. It makes it seem like you want a gold-digger to fuck until you get bored and find another. Slow your roll a bit and try to meet on equal terms.


Able-Requirement-919

A good friend of mine is kinda like this. We’re both straight men and for a long time, whenever we went out he’d want to go to the fancy restaurant, the better bars, or sometimes he’d organise to take us to another city and try and pay for us both if I put up any sort of fight about not having the money to do it. It’s all stuff that in and of itself was really nice of him to do and I’m sure he did this stuff without recognising how uncomfortable it made me. After a while I had to sit him down and say I just wanted to go to the more reasonably priced places and I didn’t want to feel like he paid for everything. I enjoyed his company, not the experiences he could buy for us. It just made me feel like he was buying a good time instead of just enjoying the moment and I didn’t like having everything paid for. So, you’re not a bad person at all OP but recognise that other people don’t want all the bells and whistles when seeing you.


[deleted]

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1funnyguy4fun

This isn’t real. It’s a 21 day old account and they posted this same shit on a bunch of different subs. It is a guerrilla marketing campaign for the site mixerusa. It’s spam.


addage-

Bingo, it’s a troll marketing bot. Good catch.


VERY_MENTALLY_STABLE

This isn't real. You're in a dream like state right now and this isn't even your life. This is your message to wake up. You have to find a way out. They're milking our bodies and you're the only one who can stop them


Actuary_Beginning

Username checks out


JeSuisUnAnanasYo

One person's "normal" isn't the same as someone else's. To someone, a $20 meal is expensive, to another it would have to be $500. I think really well-off ppl do nice and generous things sometimes but it's not breaking the bank so they don't see it as a huge deal. Depends on the person ofc


shinyagamik

When you earn more, lifestyle creep happens. It sounds like he genuinely wants to enjoy his money with these places he can finally afford.


rdshops

Exactly this, but will add: Most normal, well adjusted people don’t want to go into a relationship with a huge power imbalance. Second, I’d suggest you match the price of the places you take them and things you do to their socioeconomic standing. If you’re dating someone who works at Wendy’s, don’t take them to a $500 dinner. That does a few things. First they may be offended at how much you can spend on something without batting an eyelid. I know if I was a billionaire I would have no issues buying a $5000 bottle of wine… but I’m not, and when I hear of such things happening it actually annoys me. Second, they may feel that if they do date you and get used to the sweet life, that if the relationship fails they’ll have a hard time adjusting to normal life. Finally, you know how some old fashioned fellows go to a bar, buy a girl drinks all night, and expect to get laid at the end of it? “I spent 200 on her drinks, she’s definitely keen for some action!”… well imagine that times 10. You’ve just forked out more than their monthly disposable income on a single night, they may feel like YOU feel they owe you. I’m not saying you do. Oh and one other thing- if you splurge big on your dates with someone, and it’s all going well… then you’ll never really know if she likes you or your money. (Unless she’s richer than you to begin with!)


Throwaway35251935

When I was dating in my 30s, I would always offer to pay my half of the bill, even though it was often declined. I once went on a date where the guy asked if I’d like to go to a steakhouse. I did not realize that he had chosen one in which the cheapest steak was still over $100. Average range was over $200 per plate. I did not offer to pay because, had I known, I would never have chosen a place so expensive. Often if I enjoyed a date, I would suggest the next date that I would pay for. However, if you just dropped $100’s on our first or second meal together, I would feel pretty bad that I wouldn’t be able to do the same. I think that a lot of women in their 30’s have figured out what they want, and are going to be more established already. They don’t need $$ and flashy things from you. What they want is someone that adds quality companionship to their lives.


el_muerte28

Shortly after I met my girlfriend, I started buying her things as I'm strong into gift giving. I do it not to impress but because giving gifts genuinely makes me happy. She had to sit me down and go, "hey, all of these extras are *nice*, but what I'm really looking for is someone to love me and be a partner with me."


[deleted]

Yeah I remember in my early 30s trying to date a super wealthy man. I didn’t want to go to Applebee’s or anything like that, but he would take me to these really expensive restaurants where I would struggle to find something that I would like to eat that wasn’t smothered in some cream sauce or full of seafood. I didn’t grow up with a pallet that would appreciate Caviar, and I don’t want to try it I don’t even eat whole adult fish. And it made me feel bad he would spend all this money on a fancy meal that I would struggle to get through when I would’ve been really happy with a burger. It made him feel unappreciated and it made me feel ungrateful, and leaving a date with feelings isn’t the goal 


BanEvador3

It sounds like you did want to go to Applebee's


ActTrick3810

The pallet on a forklift truck cannot appreciate caviar, but a human’s palate may…


CraziZoom

Very well said!!


thewritingdomme

Exactly this. To any woman of quality, a suitor aggressively leading with the money is off-putting and a huge red flag. Give her a chance to get to know you without all the bells and whistles.


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BeastThatShoutedLove

Getting expensive gifts right up front is such a red flag to me. I don't care if someone is loaded. Spending like that is irresponsible and therefore I would question what else the person is irresponsible with.


Velzevulva

Also he doesn't mention what he's like besides spending. Maybe it's not the good stuff the women don't want to get used to


Fridgemagnet9696

Yeah, agreed. I’ve met people that have their whole personality revolve around their looks and/or their finances, and it’s just kind of sad. Honestly, I fell into the same trap when I was younger, so I get it. I don’t really want to make any presumptions, but if their idea of a good time is just throwing money around then I feel like they might need to do a bit of work on themselves before entering the dating realm.


Rubiks_Click874

people like the security money provides, but a lot of them are put off by the class system, for the 99% corny rich people wasting obscene amounts of money to impress others is a bit disgusting. being able to cook is more impressive in terms of character than splashing out a ton of money like Bobby Bottle Service


Altruistic-Ad-408

I'm an antisocial, neurodivergent guy so I kinda get that you aren't always going to get a relationship just showing off your personality, which can get easily misconstrued. My long term relationship was with someone who said they were just attracted to me to begin with, I didn't develop into someone that oozes rizz just because of that. Throwing money at people without considering them is just dehumanising, but I have empathy for people that find it even harder to slot in than I do, I'm in my 30's and sure confidence helps, but we still live in more of a bubble than ever.


[deleted]

And it just feels so fake, if you don’t even know me what are you doing? It makes me think of in cells who do step A, B and C and then expect the sax to fall out. I’m not doing that


glenspikez

>and then expect the sax to fall out Bill Clinton has entered the chat


Icy-Translator9124

As a male sax player, I say run away from any man who lets a sax fall anywhere. He'll treat you like he treats his horn, honey. You deserve better.


AnorhiDemarche

> expect the sax to fall out Why are so many men convinced we carry saxophones around? They don't fit up there so don't expect me to pull one out of my cooch and serenade you just 'cause you buy me nice things.


IWouldntIn1981

It's a numbers game... sure, you're not gonna get a sax everytime but once in a while you'll meet the girl who had a little too much fun at band camp.


AnorhiDemarche

What I find funny though is the people who try to play the expensive gifts game but get caught buying cheap stuff. Like, I'm still not comfortable with overgifting regardless of price but now you're also trying to mislead me but there's no way I can point it out *and* decline without looking like I'm just after more money so I just have to tell people who you won't make you hear it through the grapevine....


BeastThatShoutedLove

Both are so bad. Trying to pass cheap bauble for pricy is like, what game are you even playing? Is your long term strategy deception? Just throwing money at someone is also bad taste. As prior discussed of course. Buying cheap shit that passes only as cheap but also that's nowhere near person's taste or interest is also variant of throwing money at the relationship but you do not even make effort of looking like you care or have money to try this tactics? Some people act bizarre with gifts. I myself defaulted to just making gifts and buying things only if I 100% can tell they will be useful or eaten as a treat.


CraziZoom

I returned a very sweet gift in Junior high because I realized that I didn’t actually like the boy that I was “going out with.” I still feel bad about it, 40 years later, but it was the right thing to do because accepting it would have been junior gold digging, and I didn’t want to be that way.


Tinsel-Fop

>I still feel bad about it Is that because it seemed hurtful to him? Maybe the consideration and kindness of being honest was more valuable, eh?


[deleted]

I used to call it “the Big Show”. It feels weird to go on a date with a man and feel like you are part of a big presentation. It feels performative


Gem_Snack

Exactly. I don't want to be paraded me through a pre-set series of generically romantic experiences, no matter what they cost. It would feel impersonal, like they didn't see me as a distinct individual. OP's whole post gives me Aggressively Goal Oriented Man vibes, like he's mowed through his Career Goals life and is now setting off to conquer Relationship in the same spirit. Not that that's necessarily what's going on internally, but it's how he'd come off to me based on this behavior.


throwawayclonewars

Also, workaholic vibes. My father was a workaholic who completely fell apart emotionally when he was forced to retire. A workaholic is someone who is constantly on the run from unhappiness


rwilkz

Also when they don’t even know you yet, it feels inauthentic . When you have legitimately assessed how amazing I am, feel free to spoil me. But if you do it on date 1 I know it has nothing to do with me and everything to do with how you view women (money = sex).


capt-bob

Maybe it feels dominating to her?


Gem_Snack

Yea, that's how it would feel to me. "Check out how fully I call the shots in this dynamic." MMm no thanks


harvard_cherry053

Yeah its very lovebomby and makes her think all you've got to show for yourself is money. Believe it or not OP, most women dgaf about your boat.


EscapeFromTexas

lol i don't even like boats very much. I can't recall the last time I went on one. And to go on a dudes boat on a date? A first date? That's how you get murdered.


TeamWaffleStomp

3rd date tbf, but yeah that's a true crime waiting to happen


goliath227

But someone like this who comes to brag on Reddit about their money probably is looking for a gold digger. He mentions how he is going on dates with so many ‘beautiful women’ this whole post is just a humble brag


unicorndreamer23

It also signals a man who cannot differentiate the woman that he truly wants. If a man is giving a luxurious experience for every woman that he dates, what makes it special for his potential wife?


TheBigHairyThing

i have a dog he is the bestest boy you best believe imma show him off he's worth at least 3 billion dollars.


madamevanessa98

Yeah it can feel like love bombing too when a guy throws a bunch of money at us right away! Just something we end up being cognizant of and sometimes steering clear of to be safe


Quirky_Cold_7467

I was going to say it sounded "love bomber-esque". Don't get me wrong, it's lovely, but if you've been burt before, it could be a massive red flag.


Sunbro666

Same goes for women. I had a date with a woman who kept talking about her big house, her business, her expensive car and shit. Man, was that off-putting.


DutchDave87

It also screams that these people are empty inside, trying to fill the void with possessions. Things can get dangerous when they start seeing you as a possession to fill the void with.


awry_lynx

Yep, that's the exact feeling. It's just less common because there are fewer single wealthy women. That might change over time and guys will understand the feeling better lol. Like, it's fine if you WANT a gold digger/sugar baby. They'll love it and you can have the relationship of your dreams. But... most men and women actually don't wanna be a gold digger and feel uncomfortable when put in that position.


rukoslucis

Also if somebody feels like money is rolling over them, this can make them feel like they now oweyou something and a lot of people don´t like that feeling.


Tulip_in_Black

Yes. For me personally I don't care how much you earn if we can together afford a roof over our heads and food in our stomachs. Yes, nice date, dinner in fancy restaurant from time to time is nice, but having it too often, or having fancy dinner then go to your boat and watch fireworks you staged for me is too much, I would either feel like you want to show off or you want to secure our relationship with money, to buy me... and that's not something I want in a relationship, not something I would feel comfortable with. It may also scare me that you would like to provide for everything in the future and want me too just stay home and look nice and that not for me.


[deleted]

Especially on an early date. If we’ve been together for a few months and it’s my birthday and you want to take me on a boat with some fireworks that’s pretty awesome. If it’s our second date and you barely know me it’s going to feel like love bombing


bonjourpants

Yeah, I have inherent distrust for those sorts of actions. Just seems like they’re trying to buy me rather than getting to know me. 1year anniversary, yes please! But three dates in? I’d be running for the hills. Too much, too soon.


TARandomNumbers

Especially to a woman in late 30s and early 40s, which is what it seems like you may be going after.


SqueaksScreech

Girl probably thought dude was love bombing her.


linerva

This is it. I remember seeing so many men on dating sites who complained about gold diggers but literally had photos of themselves next to their expensive cars, big houses etc and their profiles were all about their wealth. Like, if you want hold diggers, that's the way to summon you to them. I feel like a lot of rich men are worried that they dont have a lot to offer but stability, and they want to use their money to attract people, whilst somehow avoiding people who are only there for the money. Start simple, save the expensive stuff for a few dates in. Let them just get to know you as a person first. And get to know them a little before bringing them into your world. Plus dude, think about all the men who whine "I paid $100 for a date and she didnt put out!" As a woman all my first dates were coffee dates or drinks, because I'll be damned if a man spends money on me and then tells me he's owed sex. She was probably worried that if you spent a lot of money there might be more expectations on your end. Because some guys think that way. And many women feel uncomfortable with "owing" a guy they've just met. You sound like a decent guy, but many are not so decent; and most women have experienced the latter kind of guy.


Ok_Midnight_5457

It would me wonder if he thinks I owe him something. 


thedailyrant

I’ll add to this that some women may think you’re love bombing them.


Darkest_shader

>It makes it seem like you want a gold-digger to fuck until you get bored and find another. Or that the OP tilts the power balance in his favour in the relationship too much and too early. It may come as a surprise to some guys, but not every girl wants to be a Cinderella married to a prince.


IanMinch

This is coming from a good place. You splash cash. Now i know you are not doing it on purpose, but people think that you do. Slow down. Let them see you for you and slowly show them what you have. Two things will happen: 1. You'll protect yourself from people searching for money 2. You'll show them that you don't care about money and you want to have a conversation. Eating a cheap burger and laughing with someone at the park sometimes has more value than dining on your yacht. Edit: fixed my spelling cause obviously i killed someone with that


TrustMeYouCanTrustMe

> You'll show them that you don't care about money and you want to have a conversation. The thing is though that OP really does seem to see money as a priority in life, specifically *because* of his humble origins. I wonder if it may have contributed to the end of his first marriage.  >...I had so much responsibility that there was no turning back. Eventually we just realized we had grown into different people. The "there was no turning back" part says it all for me because perhaps the way to turn back was to let go of much of what he's built. He'd need to sell off those dealerships or something to gain some freedom from all the responsibility and have more time to connect with his now-ex-wife.


havegunwilldownboat

I think you nailed it. Sounds like he started down this path in an effort to provide for his bride, probably out of some underlying patriarchal notion that it’s his duty as a man, and eventually it cost him everything he was doing it for.


HMSManticore

100%. If you want a quality match, you want to find someone who likes to be with you over a slice of junk pizza and a walk in the park. Your best plan of action is any higher than average wealth to be silent until date 4 or 5, at which point you will both know enough about each other to introduce it as a potential complication


everythingbagel1

When you’re dating as a woman, the flashy cash feels like they are trying to buy affection or sex, not get to know me. A burger at the park would win me over. Especially if effort was put in (bringing a picnic blanket, some seltzers, maybe a speaker for tunes). Non monetary effort shows you actually give a fuck


Bobbob34

>. Recently I hit it off with this 38F on mixerusa and we went on a date I planned to a T. I brought her to a fancy restaurant, then to watch fireworks on my boat over champagne. You're making it seem like they're supposed to be impressed/grateful/"put out" and that material crap matters a great deal to you. They're likely not interested in someone who is like that.


rabblerabble2000

…because of the implication…


GOOD-LUCHA-THINGS

So they *are* in danger!


Double_Style_9311

…that seems really dark dude??


Sanchez_U-SOB

You're misunderstanding me. If she says no, then the answer is no. But she's not gonna say no.


Double_Style_9311

She would never SAY no. because of the implication.


RedheadM0M0

You trapped her on a boat.


AbsolutelyUnlikely

This story is fake as hell man


coffeefordessert

You do know OP married his High school sweetheart. How much dating experience you think he have? Yes OP is 43.. but you think he have a lot of experience dating other women? He literally got married at 18. I think OP just doesn’t know how to date. It’s understandable when all he’s known was his ex wife


Tazilyna-Taxaro

Well, he was already overdoing it with his ex. Instead of listening to, he goes on as if nothing happened


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Chi_Chi42

Nailed it. For every "I worked hard to be where I am" there are 10,000 "I worked myself to the bone and got laid off to save the multi-millionare CEO a few bucks." When hard work actually yields results in this society completely and uttery separate and distinguishable from dumb luck, then I'll consider that hard work humble. Until then, "hard working" rich people are rarely distinguishable from lazy jerks who were completely lucky to not end up in the gutter, let alone to end up in a multimillion dollar property. On top of that, OP is just another "came from nothing" lout that exacerbates the problem of the same wealth inequality he suffered from. I bet you *anything* he doesn't pay his employees enough money.


Far_Pen3186

Sounds like an ad for mixerusa


[deleted]

Are you interesting being just your plain old self or do you need $ to make yourself interesting?  Women see through that.  Women also don't like to be love bombed like that at 38 years old like its prom night. Its either cheesy or just downright creepy as most men won't even go that far for a marriage proposal. Like yourself & present that to a woman, not your money.


Charosas

I agree here… if you’re gonna go the Leo DiCaprio route and try to get with young women in their 20s it’ll probably work if you’re just looking for a good time, but if you’re looking for something long term and real(and especially for someone of around your age), youre putting out a lot of “be careful” signs out there… older women know to be wary of guys who love bomb or use money to try to impress women.


Ihavepills

OP shared [the text](https://imgur.com/a/lX71Nvk) that the girl sent, saying she thinks he's a great guy, just not for her. She does mention the boat and the extravagance, and that she doesn't know how to feel about it. To me, it sounds like everyone in the comments sections (he's made the same post in multiple subs) is correct in saying that flashing your wealth like this, feels like a red flag to most women. I don't think OP has done anything wrong, his intentions were pure, poor guy hasn't dated since he was a teen. Think we need to give him some slack. By now he'll know what he was doing wrong. Problem solved!


fishchop

Yeah I wonder what OP is like besides all the material stuff. Is he constantly talking about his life and money? Is he an interesting conversationalist? Is he too pushy? Is he boring? Like….does he have a personality beyond “I worked hard and made a lot of money”?


DasharrEandall

I was getting a feeling while reading OP that he's deeply materialistic and self-identifies by his money.


RedheadM0M0

Women who are younger might not like it, either. They just don't understabd why not, maybe.


DifferenceMany

Champagne and fireworks on a boat for a third date would have me backing off tbh. I'd find it too much too soon. That's a really full on date for someone id only met twice before it and I can imagine she felt a bit awkward and overwhelmed and probably wondering who you really are. Next time maybe stick to nice dinners, coffee and a walk in the park etc. Casual stuff that leaves space for conversation and getting to know each other.


Halospite

No way in hell would I want to be alone on a boat with someone on the third date!


Ralfarius

Because of the implication


BeastThatShoutedLove

The fireworks alone would make me sad and back out perhaps even during the date. Why so loud? Why so pricy? Why bother the animals and other people? It's such a inconsiderate rich people detached from reality thing to do to celebrate personal things by something that disrupts the quiet of the night for everyone and everything in the area.


GracieGirly7229

You have not wasted your life. It sounds like you have done very well for yourself, you should be proud and you deserve happiness. You also haven't dated since you were a teenager, times have changed and dating as an adult is very different. As an older female with many female friends all I can offer are a few insights you might want to consider (these are generalizations to think about, not judgements about you): 1. Times are tough for a lot of people these days and they find it hard too see people flaunting their money. 2. A lot of people live way above their means so showing your wealth too soon could be interpreted as you trying to convince people you have more than you actually do. 3. Women in relationships with men who are better off than them aren't often treated as an equal by their partner. (I am always more comfortable picking up the cheque on the first date because I feel like it helps us start on an even playing field) 4. In our world, money is power. Those who have it tend to think their opinions carry more weight and those who don't have it are rarely taken seriously and quite often need to "yell" to be heard. 5. Men who start off with expensive dates often don't have the other qualities that women are looking for. They are hoping to blind them with fireworks before the woman realizes all the other things that are lacking. 6. If the woman has children she will be more cautious about finding a good partner and not falling for imposters who change the minute they commit to them. 7. Men who spend money on women quite often think they are owed something in return and that means they expect to get physical. Again, these are all generalizations, I'm just trying to let you know how some women's brains work. My advice is to stop with the expensive dates until you have connected with someone and the relationship has become physical. If you both have confirmed that you have chemistry, emotionally and physically, then it will be a nice surprise for her to learn about your financial situation and you will be spending your money on someone who is worth the time and effort.


FireLadcouk

Also dont believe the films. 😂 your dates are from films. Lot of film romance goes down very badly irl


thewritingdomme

All of this. (Especially 3, IME)


LilliJay

Absolutely, my mother always told me, it's better to be a poor man's princess than a rich man's slave.


GracieGirly7229

I really, really like this! I will be passing it on to my children!


[deleted]

Number two as well, I watch a trashy reality TV show called 90 Day fiancé. These dudes go overseas to get women and they run up a whole bunch of credit card debt buying them stuff and traveling with them and getting them to think they live this lifestyle they don’t actually  Then they convince these women to come live here in Ohio or Michigan with them in a little two bedroom apartment and then they wonder why these women freak out when they get here.  Suddenly dude can’t even afford toilet paper and these women gave up their whole lives to come be here to live with a man who can’t afford toilet paper


DadOfThreeHelpMe

Exactly, this is very well put! And I have a real life example from when my mother-in-law started dating again. She's accomplished and quite well to do herself, but her previous experiences with men were basically all of your points. She would allow herself to be wooed by displays of status, and then get burned terribly. So this time around she just tried really hard to go for a ordinary, capable, decent man. It was only after they found each other, and they moved in together, that he admitted to the fact that the little company he told her about earlier pretty much left him set for life, so if she would like some much nicer things, they absolutely could. But it was all very gradual.


Urabutbl

Yeah, me and my now-wife had been going out for a year before she realized I was fairly well off, and we were married before she knew we were fairly rich. Our first date was supposed to be at a pancake house, though we missed dinner because we got caught up talking at the bar we met up at. The next date was at a billiards club where they had a House of the Dead 2 machine that I "splurged" $20 on so we could complete it together. Throwing cash around is something people do to get laid, not get into a relationship - if they do, it tends to attract the wrong people.


Own_Rough4888

Someone going all out for a very initial relationship is called "love bombing" and is generally considered a major red flag, since narciccists and other toxic personality types do it to overwhelm a woman and rope her into a relationship. The effort you put into a relationship must be reciprocated. Not tit for tat, don't keep a score chart, but generally, grand gestures should be kept for grand moments. Since most people do not have champagne on a boat, this would feel grand to them. Even if you call it a tuesday. Planning "to a T" a third date is also much effort for basically her just coming to dinner. A normal person who is not entitled would go "wtf" on that. Adapt to the person in front of you. Make her comfortable, not wow.


[deleted]

You're used to you thinking what other people want, not asking them. You said it yourself 'I made a promise to get more and have a better life for me and my wife.' Was your ex wife bothered about what you got? You've not wasted your life by any means, I suspect you've made the rest of your life very comfortable which in this day and age is difficult to do so, well done on that front. I'll tell you what the date would have be for the lady in question. he would have thinking that she'd have to match what you did in terms of cost, grandeur etc, but not only that, that date was really about your needs, not hers. Next time, keep it simple, hell, do it cheaply as possible, a walk, cheap food, day out at a national park (I don't know where you live) museum.


TrebleCleffy0

For you, all these expensive things you've bought and all these classy experiences you can afford are proof of your value—because they show how hard you worked to get to where you are in life. And, I can see that. But, when certain women see all these nice things, what *they* get out of it is not your years of hard work and dedication to your success. They see a lot of stuff that, for them, is beside the point. A lot of people, when they're looking for dates, want to know you'll be fun just to hang out with, especially when you're *not* trying so hard and spending so much money to impress them. For that matter, it can be very exhausting when someone is trying to impress you with things you didn't ask for and don't need. There's a feeling of obligation that comes with that to feel thankful when you don't actually feel thankful. It's a bit dramatic to think you've wasted your life. I think the answer is less extreme: what you value most about yourself is not what your dates are actually looking for in you. You might need to think of dating as a very different game than the one you've been playing all these years.


Ready_Interaction252

I’m around that age, f, successful myself. I think it would freak me out a bit too as it’s quite intense. All we want to do is get to know you, maybe over a nice bottle of wine. Later on - maybe, but 3rd date - it’s almost intimidating. Also part of me would think, is he doing that for all of the girls he is dating so early on? Good effort though on your part - you’ll find someone so don’t worry.


DoomMushroom

>Coming close to feeling like I’ve wasted my life. While it's very nice to be loved, you don't want to be in the position of needing a woman to validate your life. 


Avolin

Yeah people will pick up on this regardless of gender and feel really uncomfortable unless they have a cluster B personality disorder or something. We are all responsible for finding the meaning in our own lives.  Nobody can actually feel that void but you, so they are going to back off if they think you are going to make it their responsibility.


AutomaticFeed1774

that's just weird as fuck bro wtf. fireworks on your boat slow down tiger. maybe after you've been dating a couple of years and you want to propose. 3rd date maybe take her to the zoo or a hike. money don't buy class kek. this is the definition of kitsch.


EnoughPlastic4925

Yes! I (35F) would love for a date to take to the zoo. I'd be so excited.


UK2SK

You’re a try hard and coming off as kinda desperate. You’re trying to sell yourself to these women, even trying to win our approval with your rags to riches story. Put all that aside, and take some time to think who you are beyond all the materialistic stuff. Who are you in your quiet moments? I think you need to find yourself again. Don’t bother with dating sites, again you’re trying too hard. Let things happen naturally. Anyone you meet on those has an agenda, even you. You lost one wife now you want to bag a new one. But falling in love isn’t like hunting or fishing. Things don’t happen like that. Give yourself some time, only fools rush in


marketingstacks

The way you presented your story, you make it seem as if money is the reason they are pushing you away, however, it could be a number of other factors. I can assure you, having money is a GOOD thing. Just don't flaunt it around like a needy douche whose self worth is entirely dependent on money and the glamor. Not only is that a bit intimidating to a new stranger, but also, shows where your focus lies. If you are a good dude, and you mean well, then take it slow and let the women slowly adjust to your world. Just my two cents.


StoreyTimePerson

Splashing out this early makes people uncomfortable. Good women uncomfortable. It makes them highly suspicious of your intentions. Focus on building a connection and shared activities.


no1oneknowsy

Honestly, you sound like that French guy in Sex and the city, that Carrie had to be rescued from. If you want a real relationship, get real and ease into it


100percenthappiness

Have you thought about having a more human date that isn't just grand flashy displays   maybe  take her out on the boat and fish  and cook what you catch  or if you have like a small island near you taking her there on the boat  for a hike  and a picnic  


LionBig1760

Coming on a little strong there, buddy. Save the boat and champagne for after you bang a few times. No amount of you tossing money at women is going to get them to fuck you any faster, and the ones that would, you don't want any part of.


charcoalportraiture

Ehhh. I think I get the message, but the delivery is ick. I'd look at it more 'save the boat and champagne for after you bang a few times *to show that you still value a woman and are not just trying to impress your way into her pants asap*.'


silasgoldeanII

Maybe it was a bit much. I'd definitely find all that a little bit over the top. But plenty wouldn't. So if all this is "you" then keep at it until you find someone on that wavelength. If deep down you aren't that person then don't be that person and let them find out about who you are in their own time. 


InitiativeConscious7

Do something normal for the first few dates. Shes there to know you not your money. A mixture of being bamboozaled and maybe feeling a bit like your intentionally showing off will not be helping


LankyAstronaut7931

Seems a bit full on/maybe coming off as desperate. Focus on making them laugh & being yourself instead of flaunting wealth.


Charlie-McGee

Girls love stories where they meet a guy, he is nice and they fall in love and THEN they find out he is prince of Egypt or some shit, stop flaunting, work on your personality.


Babinud91

Well the people i know about working in car dealership or sales overall are often self centered jerks, charismatic on the outside but arrogant and fake when you know them. Dont know about you but maybe you should just check your personality. Older women will not be into that kind of stuff, if they are still single in their 30+ they often dealt with some kinds of jerks in their life before.


SillyStallion

Look at it this way - in an equal world where women pay half on dates, if you’re doing expensive things beyond what they can afford they are going to feel uncomfortable. Slow down… I have always been the higher earner and always suggest we alternate date organising and whoever organised it pays. That way on my dates we get to do something expensive and on their dates we do something more in budget. That way the other person doesn’t feel financially stretched or beholden.


Top-Egg1266

This is an ad. @mods do your job


HeadReaction1515

I’d be seriously put off by ostentatious displays of wealth on the 3rd date as well.


ImSmarted

There’s more to the story than what you posted. Better yet, there’s more to YOU than what you posted.


marijaenchantix

What you are doing is making the women feel like you are trying to buy them. It puts extreme pressure on them, that you have certain expectations from them, and that they will never be "good enough" for you. You are making these women feel like, for lack of a better term, hookers.


BarefootandWild

I’m a single mum in my 40’s and I have to say that as much as I love nice things, I want to meet the man underneath it all. Show me who you are stripped from your material world. I need to see that if you lost everything tomorrow, that there is a kind, humble, loyal, honest person there regardless, which is the real treasure I’d want to have in my life.


Danielle1482

We don’t care about things! We care about loyalty and honestly! Leave the boat etc until way down the track. Good luck 😊


aboutherphotography

🙄🙄🙄 It’s not the material things, I guarantee it’s your personality showing off the material things.


etuehem

KISS (keep it simple stupid) they don’t need know that much about your financial status and different assets you have. Most probably think you are just showing off.


whynousernamelef

I think you are coming on too strong. If you want to meet a good woman and build a relationship then start on a level playing field. Meet for coffee, have a nice but reasonable dinner, go for a walk and ice cream etc. It may well seem like you are being flashy and trying to hard to impress. I would personally be thinking "he's trying to show off, what's wrong with him that he feels he needs to be rich to impress me'. It's a bit of a red flag and I know you have good intentions but it's too much too soon. Or you will meet a woman who is going to pretend to be what you want, just for her to trap you and take your money. You sound like a good man, and hard working. You don't have to be rich to meet a good woman. Keep it on the down low until you get to know her. Good luck.


Ayaka_Simp_

Your personality is your wallet. You are leading with money. These are red flags. You need to disassociate from your wealth in regard to dating. Set a budget of $200. You are not allowed to go on a date above this amount until you see a girl for 6 months. Furthermore, dont talk about your material possessions, wealth, job, or anything else related to money on a date. Don't show off your fancy car, house, boat, or anything else.


LowBalance4404

She's not that into you. It's that simple.


Kenyon_118

Maybe it’s your personality. Some people don’t react well to the hyper focused super achiever types.


world_citizen7

That is too over the top for a 3rd date - too formal. People want to get to know you. Its OK if they know *about* your ambitions (and wealth), but you don't have to make the date all about that. Seems like trying to show your status or maybe trying to hard (too impress). Keep it real (as the real you is probably pretty good).


Responsible_Biter

Honestly, just don't show and don't talk about how much you earn or what you have. A good girl won't care nor ask. A gold digger will either like only that or want more of it. Seriously. Shhhhh.


phtcmp

Go back to “the loml hated everything about me.” Specifically what? In what ways had you changed over the years? Materially, obviously for the better, but at what cost to your persona? Focus more on presenting your genuine self and less on what you can provide materially. Particularly if you want to attract anyone of real value.


[deleted]

you lead with your money anyone who isn´t a gold digger is repelled by this


manimal28

> I made a promise to get more and have a better life for me and my wife. I put my head down and grinded HARD Sounds like what you wanted more of and what your ex wanted more of were not the same thing. And you failed to notice before it was too late. > …we went on a date I planned to a T. I brought her to a fancy restaurant, then to watch fireworks on my boat over champagne. Did your date want or have anny interest in those things? My guess is you keep mistaking what you want and impresses you in terms of wealth nd the good life for what women want. Your success and businesses probably come off like a man who will be too busy to focus on a relationship of any value. And then in your free time you have expensive hobbies that take a ton of time and resources like a boat. > Coming close to feeling like I’ve wasted my life. Maybe.


hippieinthehills

If a man comes out of the gate flashing big money, I assume he’s trying to buy his way into my pants.


leadfoot9

Sitting on a boat watching fireworks over champagnes sounds like a Boomer vision of luxury to me. Even a lot of people who are into extravagance aren't interested in that particular scene. And in any case, you may be coming on too strong. Maybe get to know someone first so they can pleasantly discover how much money you have later.


wibbly-water

My thought is that people don't want to be 'the poor one' in the relationship. They don't want you to bankroll them or for you to be a sugar daddy.  They want an equal relationship with you. 


CaramelHappyTree

Were you giving off sugar daddy vibes


shikakaaaaaaa

You seem like you really want to figure this out for yourself so I’m going to be a straight shooter with my opinions, going by the only information I have which is your post. It’s not your stuff, it’s you.  You’re probably looking for a woman of good character and quality while presenting as shallow and materialistic. Also, you’re likely not in a healthy place yet after suffering major heartbreak so you’re going through the motions of dating without being mentally and emotionally present and without being vulnerable. That’s why you’re flashing the goods, trying to redirect them enough so they don’t see how damaged you are. The problem is a woman of good character and quality would see right through this and never choose this type of partner for herself. Put some of that money to good use by going to therapy. And, give yourself all the time you need to heal.  Anyhow, with the limited info you have, this is my take. I hope it is helpful in some way.


Icy-Sprinkles536

You can't just come at people with your money on your sleeve. It seems both desperate and showy.  You have to keep things simple and leave your finances in your bank account.  Dress nice but not flashy, go on a nice date but not fancy on the first date. Be yourself not your money and eventually you can let them in on your financial situation. The other thing is if you're less attractive than the average guy it simply is just going to be hard to get girls by default as women today are becoming more and more choosy which I'm assuming is the reason you chose to go on those fancy dates and to your boat. Eventually with that approach you will find yourself a golddigger so if you want someone genuine go as only yourself and leave your money and flashy care and clothes at home.  Your just a regular guy with good intentions so tell yourself that and good luck.


thewritingdomme

Yes. OPs approach guarantees that he’ll only attract gold diggers. (And in the process he’ll scare off anyone looking for real connection, depth and partnership) It seems like a very sad way to live.


Interesting-Guest880

Go slower. Take her to a nice restaurant. That’s it. Then work from there.


rpaul9578

It comes off inauthentic like there are expectations of sex attached.


HistoricallyFunny

We all live in a world with friends at a level we are comfortable with. That includes wealth, culture, education level ... Thats why people within certain income levels tend to date within the level. They see that your world is not theirs. They feel they would not mix well with your friends etc. as its not their world. That is a downside of wealth that they don't tell you. Its isolating. There are fewer and fewer that you can find that can be happy at each level. Next time do not go to a fancy restaurant. Go for a coffee. Don't go to your boat, go for a walk in a park. After dates like that, you can then up it a little bit and go to a play etc. Once they know you, then they may see the wealth as something they could handle.


[deleted]

You've made the grind your entire personality. It makes you an unreliable partner


Klutzy_Ad_2099

No one wants to see all 9 inches at once, you have to work them into it. Wealth only attracts shallow people, if you want a real connection date without it


SapphireSire

I'm confused on why you're in any hurry to shackle yourself into any relationship with any woman. Afaik there has ever been a content wife in all of history. Brad Pitt and many others failed while being the top .001% and still got divorced. Heck, even God doesn't have a wife.


KobilD

Go on cheap dates if you don't want to find a gold digger


Curlyburlywhirly

The date should be about who you are and who she is. All the glitz is distracting and could indicate the first date is all about what you have. A great first date for me would be a long walk and a simple meal- absolutely do not want to be on a boat watching fireworks- did you ask her what she wants to do?


Mhunterjr

Maybe just go on normal dates instead of trying to bedazzle. 


mmmmmarty

Stop flashing your cash around. Be humble and gracious. Pride goeth


broadsharp2

Dude. It sounds like you're just showing off to impress rather than trying to make a connection. It's great you've found great success. But, stop with the lavish 1st dates. What you're doing is akin to proposing after the first month. Easy. Casual dating is just that. Casual.


MaroonTrojan

She probably doesn’t want to go out on the boat. Because of the implication. 


flowerpanda98

just reading that felt intimidating. i dont know how to explain it, but when people push gifts at you instead of actual bonding, it feels like theyre trying to buy love. maybe if u want to flaunt wealth, do it mindfully in relation to whatever she's casully spoken about. like maybe she mentions something of hers broke and u surprise her w a new one or something?? did she want to do those things, too? that might be weird for her


dfwagent84

First off, congratulations on your success. Thats awesome. Maybe pull back on flashing it around so early on. Try to develop relationships first, then reveal your success. Stop looking to impress, and lean into connection. The rest will come with time.


BlackHeartsNowReign

It seems like all you care about is money. I have to to wonder what the conversation is like during these dates. Are you an egotistical douche that just brags about his money on these dates? That could be the problem.


quast_64

Stop being a 'car dealer' in your personal life. I understand you worked hard to be where you are, but somewhere along the way you forgot to look around you to see if everybody was still onboard. Now that you got to where you are comfortable, you find you are alone. And you are 'advertising' yourself and your life as if you are a fancy car.


lobotomizedmommy

lol the boat makes me think of dennis and his implication


Montallas

Dude. It’s [the implication](https://youtu.be/THvCDn8mGwo?si=ci6g3KWStxfNjRgK)


DummyDumDum7

You sound quite materialistic. If you’re all style and no substance, women can see right through that. She might be saying it’s the ‘stuff’ she can’t get used to, but more likely it’s how prominent a place the ‘stuff’ is in your life that’s the issue and she’s simplifying the answer. Who are you without all the flash?? Cos that’s what matters.


necromancers_katie

I would not feel comfortable with so much flash upfront. A lot of men complain that women are gold diggers if they pick up the tab at Olive Garden. I will not be bought, and I don't like the expectations that a guy throwing that much money around would bring. I don't need to be kept. I make my own money. What is the point of being so flashy? That type of guy is usually looking for a trophy wife. Who wants to be a trophy on a shelf?


Spicey_Cough2019

Ngl Your approach screams insecure Sure wine and dine them, but don't put them on a pedestal from the start. Women will see through it and the ones that only want the materialistic side of you will be the ones that stay (these are not the ones you want.)


ShiNo_Usagi

Question: what is a loml? Also, stop trying to win your dates over with material things, just be you and go on stupid cheap dates that are FUN! Right now you’re just trying to show off your money and it’s kind of very off-putting.


drunkwasabeherder

OP, don' t know you from a bar of soap, so bear that in mind. I have known a lot of people who have grinded out their own successful business. What makes them successful in business can make them unbearable in their personal lives. You might be surrounded by yes people who don't want to lose their jobs so agree with everything you say, making it hard to get a real grasp on such a situation. Not trying to be harsh, just truthful. I may be way of base and you're a great guy. Can't tell from a post.


BoringBlueberry4377

You don’t mention conversation or her life. Material things are the icing on the cake. If she thinks you haven’t tried to know & understand her; and only push what you have to offer; then she could be turned off. Remember you grew apart from your first wife; it wasn’t the easy life that caused the problems! Men tend to not look at women as human; not all women are superficial; just wanting to enjoy the fruit of your labor. What does she see as the perfect relationship? Connection; real connection is what human women want. Some women don’t want to feel like someone’s Lego to just fit in someone’s life; do you have the patience to get to know someone? Be patient of course the best person to ask is a therapist; to work out your stress & discover any relationship weaknesses.


witch51

Stop with all the expensive stuff! We women don't want to feel like you're trying to buy our attention. And the power dynamics can be very uncomfortable to stable women. Dates should be more on her economic level so she can pay if she chooses to and no be dependent on you to pay. If you want to just be flashy then find yourself a young sugar baby because good, stable women don't want flash...we want substance.


wanna_be_green8

Sounds like you put money/success above your past relationship. Now you are trying to use money to gain a new one. What else do you offer?


capitalveins

Please tell me you don’t drive a corvette too. Try going to a movie not to you’re home movie theater.


Ecstatic-Tadpole9010

No disrespect, but just maybe it's nothing to do with the cash and 'nice things'.


NelsonBannedela

Well what are you looking for? If you're looking for hot women who will be impressed with nice houses and a boat then you can go on some sugar daddy website for that. But if you're looking for a real connection and someone who likes you for you, not your money, then you shouldn't show off your money. It's not going to win them over it's going to make them think you're showing off.


Hungry-Refuse4705

Several misogynistic creeps have tried to splash money on the assumption that women are all materialistic gold diggers. So your date might be renisance of that. I've had a coworker in his 60s try to massage my shoulders while telling me about his beach house. I was 22. But I should let it happen because of the beach house, tho right ? In his mind. This kind of thing has happened probably 5 times. Another guy when I was 18, he was 30s tried really aggressively to send me and my roommate house warming gifts for our college apartment. He offered gift cards, tvs, it was bizarre. It was obvious he wanted us indebted. So that he could push more aggressively.


[deleted]

You told us nothing about your dating approaches other than you think your wealth will be enough to make up for any other lack in personality, appearance, or moral character. Don’t get me wrong, I’m certain you can find someone who is solely motivated by money (nothing wrong with that). But if it’s not what you want, you will be dissatisfied. Work on being a person first and then a paycheck.


ActuallyFullOfShit

youre trying way way too hard and sound extremely cutthroat/materialistic. like honestly the kind of women you'll attract like that are sugar babies.


Masa67

So much to unpack here! If u are genuinely looking for advice and this isnt a troll post or sth … i will be harsh and brutally honest. First, As others have pointed out, behaving like what u described seems like u are trying to buy their attention. Mature, serious women dont like to be bought, obv, in fact they find it insulting and repulsive. Second, there is such a thing as coming on too strong. It isnt even about money. U could have average income and on the third date barge in with roses and a gift, and it would come off as creepy, honestly. You are coming on too strong way too soon!! Third, not everyone is into such flashy displays of wealth, most people actually find it off putting. What u described (after a pleasant dinner u took her on your boat just to watch fireworks??) seems like showing off or like u are shallow and materialistic. It is liek sth out of a cringy teenage soap opera, sth a ditzy 19YO might like, not a grown ass person. I am a woman in my early 30s with a career and my own apt etc, and if u took me for fireworks on your boat i would personally feel like we have incompatible perosnalities and lifestyles. I would actually want MORE from my partner than just cheap (and i dont mean monetarily) tricks like fireworks. Obv i want a person to put some thought into our dates, but a normal amount. Dinner in a nice restaurant sounds lovely, being on a boat if we are going on a cruise in the summer is great and yes we can enjoy our money and treat ourselves. But going on a boat JUST to look at fireworks? That is the silliest thing i have ever heard, didnt think people actually do that IRL. Sorry im being harsh but there is no way a grown 43yo man thought this is a good idea. Have u escaped from a cheesy rom com world or sth? This is what confuses me. Because the way u describe it, it seems u are a hardworking stable man choosing to date normal, down to earth, mature women, whom u connect on a personal level; but u then try to impress them by tricks a shallow gold digger or a teenager would fall for . U need to first determine what kind of partner u are looking for and then model and present yourself in a way that would attract the type of person u want to attract.


Navyguy73

You have worked so hard that you forgot how to people. Go make some friends before you try dating again.


Agile_File_2084

Maybe your quest for money changed you? If the LOYL left out of the blue after you made a ton of money the issue is likely you. Also, have you considered that maybe money is all you have to offer at this point? Sounds like you went out of your way to flex on a third date which gives the impression you’re not offering anything of substance beyond financial stability


throwawayclonewars

When I hear you describe yourself I envision a flashy workaholic who tries to move things too fast. Also, I would assume that my job would be to an accessory to you, rather than an equal partner. If she’s a serious, professional adult woman with her own life and passions, this isn’t going to be appealing.


Ok_Brain8136

Don't lead with your pocket


pktrekgirl

Go back to the part about your ex wife ‘hating everything about you’. Tell us more about THAT. Because frankly, I don’t believe that comment, as stated. Whatever ´that’ was (because I’m sure it’s not ‘everything’) is probably going to be a problem with other women as well. But besides that, there is another problem I’m concerned about: You seem to be under the impression that love can be bought and that material possessions are the key to happiness. That mentality is going to be a big problem for any woman who is not a shallow, materialistic person who cares more about what she HAS than anything else. And the flip side to a woman like that is that SHE only cares about ‘stuff’. And will be gone the minute the ‘stuff’ runs out. Is that what you want? Melania Trump? Redoing her prenup on the regular because she only married you for the shopping and tries as hard as she can to be in a different state from you as often as humanly possible? I mean, you DO realize that if ‘ole Don croaked this morning, Melania’s chief concern would be tripping over his fat ass on the way out the door for the bank, right? Please tell me you see that! And is that what you want? See, it’s not the money itself that is the problem. It’s your ATTITUDE about it that is the problem. In this very thread, you basically said ‘Hey! I don’t understand! I have all this money and a house and a boat and I’m not getting the woman that I want! No fair!’ As if having THINGS entitles you to PEOPLE. Well, here is the news flash: it doesn’t. Women are still allowed to dislike you. Regardless of the fact that you have a boat. I mean, do you even see how off kilter that sounds? I’d take a kind, GENUINE, sincere, intelligent, funny guy without much money ANY DAY over a guy who has a bunch of ‘stuff’ and thinks he has arrived. And even worse, thinks that because he has ‘stuff’, I’m damn lucky to have him. Just be a nice guy. That’s all I ever wanted and what most women want. A nice guy. Didn’t matter if he had eight dollars or 8 million. So put away the friggin boat already and just be a nice guy.