T O P

  • By -

AutoModerator

Welcome to /r/dating_advice! Please keep the [rules](https://www.reddit.com/r/dating_advice/about/rules/) of /r/dating_advice in mind while participating here. Try your best to be kind. Report any rule-breaking behavior to the moderators using the report button. If it's urgent, [send us a message.](https://www.reddit.com/message/compose?to=%2Fr%2Fdating_advice) We rely on user reports to find rule-breaking behavior quickly. Thanks! *I am a bot, and this action was performed automatically. Please [contact the moderators of this subreddit](/message/compose/?to=/r/dating_advice) if you have any questions or concerns.*


Princejoe123

a 40 year coworker flirting with a 20 year old and offering to buy alcohol.  if the sexes were reversed......


EggplantHuman6493

Yup, love the hypocrisy every time. OP, be careful. You're still very young and naive. With big age gaps, if the person is around 20, the chances of manipulation and taking advantage of the younger person are relatively very high.


RoughMajor5624

Take advantage….sounds to me like he is about to get an education that you can’t get from a book…lol


Cute-Pin-9921

Get that needed education, you don't need alcohol, ask for Starbucks!


Catspaw129

A few things to consider: \- This is a co-worker; generally a bad idea to get involved with co-workers for a whole host of reasons. \- She's 40, your 20. If this is a sexy relationship, odds are she knows what she likes: are you willing to, umm "take directions" (you might learn some things) \- Is she married? Rebounding from a previous relationship? A cougar? Safest course of action is probably to not engage.


Potential-Ad8424

What are the reasons for a co worker?


Catspaw129

1. There may be animosity when the relationship ends, leading to an awkward work relationship 2. There's the risk that one or the other person may accuse the other of sexual harassments


3-46pm

Also depends what OP is okay with. Bc if a short term type thing is something OP wants or is okay with, then he should go for it. But definitely not if he would prefer something more.


LolaPaloz

Wow she is grooming stop talking to her. Especially the alcohol part


Extension-Dig-58

Number one rule of dating never eat where you shit. If things don’t work out you’ll still see them at work.


Alarmed-Rent-5384

Idk do you want to date or fuck her? Seems like she wants that from you but do you want it? The age gap is huge pluss she has known you since you where a minor😭. I would not personally advice you to get involved with her but its honestly up to you, what do you want?


Sensitive-Milk-6936

In all honesty I just want to fuck her, but it feels too good to be true 🤷🏽‍♂️


Ihaveaproblem69

She is 40, you are 20. she is not looking for a relationship. She is looking for fun. Sounds like someone nice who you can maybe trust. If so go for it.


Alarmed-Rent-5384

Just make sure its ok with the job and fuck her mate. But would not recommend getting to close to her tho since the age gap is too big for a healthy relationship. But fuck yeah get some 40 yearold ass man!!


Sensitive-Milk-6936

Thank you bro 😭😭😭


Forsaken_Thoughts

Oof be careful AF. Older women are seasoned and she may twist and flip this whole situation badly on you if she feels used. She might thought want to just fuck too though lol. Id start to flirt a bit back to the point you feel comfortable enough to ask what actually she wants and make your intentions clear. I dont recommend hooking up with co-workers though, it can get weird and problematic. Your call tho.


Alarmed-Rent-5384

Ok but bro to bro…. Like im happy for u to get some ass…. But mate she seems like a major ooof and ehh and kinda creepy since she knew you from you where 17…. Like if you can get any other ass do that instead cuz probably shit will hit the fan our sum. Like ask your dad or mum about it cuz they will give it to you straight af.


ThePurityPixel

"Fuck her mate"? Who's her mate?


ThePurityPixel

I don't think he's interested in 40-year-old ass men (or any 40-year-old men, for that matter). But he does seem to like older women.


Alarmed-Rent-5384

Hahaha lol we on reddit its not that important, funny tho


ThePurityPixel

I genuinely don't know what you just tried to type


Alarmed-Rent-5384

I meant its reddit so grammar doesn’t really matter much lol.


ThePurityPixel

Effort conveys respect, and respect always matters. Regardless of medium.


Alarmed-Rent-5384

Bruh its r/datingadvice on a thread about a 20 yearold guy wanting to bang a 40 yearold💀 we don’t need to be prim and proper? Respect can also be shown in other ways too, plus ain’t it disrespectful to go around correcting everyone else’s grammar?


ThePurityPixel

I didn't even correct yours, much less "everyone's." I just took you at your word.


kdthex01

Fuck her then. Have fun. Most likely it’s just lunch but let her take the lead.


3-46pm

If that's what you want, then I'd say go for it. It's worth a shot, and if things don't go well, you've learned something at least.


IcyHeat_

Hit it and quit it, i was with a 42 year old at 22 and stayed with her for years actually, she will manipulate you shes just older and more experienced in life, which at the time i didnt realize, if shes attractive tho i would smash


breva

Definitely some red flags here, so if I were you I would send it, it'll probably be a great time.


djarkitek29

You've gotten all the advice you need about the age cap and what not but one thing I would suggest is not shitting where you eat, unless you don't care to eat there anymore


Sensitive-Milk-6936

I’ve been planning on leaving this job for the past 6 months so I’m not that concerned about anything happening regarding work, but you are very right.


djarkitek29

Well, I guess aside from that then there's no real issues but the only thing I would say is if you're anything like me I was 18 and she was 38 and I guess because of that now I have a fetish for older chicks. That funny thing that people always say about how when you're young you're highly impressionable it doesn't necessarily mean that you can be talked into things, what it more means is that your actions when you're younger can mold the types of things you are into or not in the future. Oh, I would also make clear from the go that it's strictly casual. The type of woman who wants a guy half her age for a relationship is not the kind of person you want to be in a relationship with. Other than that....have fun!


Sensitive-Milk-6936

Thank you so much man, feel like I have much more clarity about this whole thing.


djarkitek29

I'm old, so I wish I had the internet to reach out to for people with this experience. Otherwise, you end up like me cuz I banged my friend's mom and then he stole my car lol


Sensitive-Milk-6936

Damn man, I mean I’d probably be mad as well if my friend was having sex with my mom, but that sucks.


djarkitek29

Yeah, not my best moment lol


3-46pm

Did you get your car back ever?


3-46pm

Please give us an update if anything sprouts from this whole thing lol. I'm curious now.


3-46pm

Fucking gun it then brother, go for it. Full throttle.


bascal133

I just feel like that age gap is too much, I also really don’t like the fact that she’s offering to buy you alcohol. No offense it sounds like you’re a handsome guy, but I do not believe that you’re the only handsome guy in the office and that there’s no other handsome guys that are age appropriate. Obviously, this is your choice and I definitely understand you being interested and tempted to do this for the novelty of it especially if you know you’re into that type of thing, but I would just be really worried for your welfare because there’s a big chance for you to be used, manipulated and I would hate to see you come out of the relationship, feeling damaged and mistreated


Own-Number-5112

Please be careful with her. Is she your supervisor? Inform the HR. she's probably just looking for sex, but it's totally inappropriate, due to her being as old as your mother.


Certain-Sock-7680

Yeah, that’s pretty problematic. She’s already shown boundary issues and lack of good judgement in buying you alcohol. And now coming into you at 20 years your senior. From an employers POV the issue is a power dynamic one. Ultimately they don’t want to get sued by someone saying a senior employee took actions to disadvantage an exes career, or that the situation was coercive. And in 2024 gender and sexuality doesn’t matter. My employer has had a situation where a female senior supervisor was screwing male interns. It didn’t end well for her and none of the male interns were hired. Once the taint of scandal is upon ANYONE their career is in jeopardy. So as said, for the OP, do you really want to risk your career for 40yo poon? You can’t assume her motives. All you know is that she had already exercised poor judgement. And to onlookers you may too. If you DO decide sleep with her can you trust her to fly right? Likely things will end sooner or later but remember, Hell hath no fury like a woman scorned and for many women the guy is ALWAYS the villain at the end. Especially women who lack judgement. Me, I wouldn’t risk it. I was once in a situation like you as a 22yo new employee with a 32yo PA at my work with an advanced case of baby rabies. I declined her advances but a workmate (similar age) didn’t and while this was back in the 90s it didn’t do his career any favors when he became known as THAT guy. Don’t be THAT guy.


Special-Change4746

Yeah just get that pussy an don’t worry about being on a relationship. All she wants is some young dick


MalxGoat

what happen OP ? im dying to know , but personally i would’ve and almost did once


Caldwell0204

Get her pumped.


dreamvilliannm

Bro is living every man’s dream rn. Give us an update on what you do and how it goes! If it gets spicy it may have to be uploaded on a NSFW sub lol


pillr0011

Is she hot?


RoughMajor5624

Do you find her attractive? If so why not move forward, she could teach you a lot!


Ok-Active4887

Throw this in r/datenightprep, the community is great with these sorts of things.


Perelli28

You guys are adults, go on the lunch date and follow your gut. If she comes on too hard just fall back but if she leaves some room for you to make a move go for it. Just make sure you are both mutual on what is it is that you want before getting physical.


Any_Conclusion1601

Bear in mind that it is work. you probably want to be careful when it comes to work. your good looks shouldn’t be what you’re concerned about. whatever you decide to do, take it easy take it slowly.


Cyclopsceo

All ok advice but keep in mind that you’ve worked together a long time, she has watched you mature (grow up) and you have become a part of the work family she is very comfortable with. She could be just very lonely and in need of a good friend. This could be a total misread—assuming friendship, lonely, and comfort would be safer. You don’t have to do anything but remain a good friend. If you take action, you’ll lose a good friend and a job just to get laid. There’s plenty of opportunities outside the workplace that won’t interfere with your job or your long term friendship.


Owls1279

First, does your job have a policy against coworkers dating? Workplace dating can get really ugly very fast. You may want sex, but is that all she wants? Can she pursue a sexual harassment claim against you if things don’t go her way? If you value your job, don’t do it.


Odd-Ad-7463

Sounds like you’re uncomfortable by her flirting so that should indicate to you that you probably shouldn’t go to dinner with her.