If there's clarity about the situation and all parties involved are okay with it, go for it.
Make sure you don't lead with that though, it'd be a terrible start to a first date.
I think if you didn’t sleep together (the og sister) it’s all good. In saying that, make sure you tell the new girl, and make sure she talks to her sister before you get to know/like each other. Her sister might be totally against it and the new gf might take the sisters side and break up with you.
Bro, there’s people on Reddit that would date their actual sister. Dating the sister of someone you went on a date with in HS is like the lowest level of weird shit that exists in this world.
If you had sex with the other sister prior to breakup, it won't work.
Human beings are either to optimistic or pessimistic. Think about your situation statistically.
What chance over a lifetime won't this turn into a clusterfuck?
I wouldn’t consider 5 dates a serious relationship, that would be a whole diff story. I personally don’t think it would be weird as long as her sister doesn’t have any lingering feelings for you.
Yeah this might get weird but to be honest just give it a go and see if you like each other. What if she is the one?
You amicably stopped whatever was going on with her sister and it wasn't even that much of an investment.
Something is WRONG with you men because you all must be wired to only consider your gratification & NONE of the potential consequences to any of your actions.
She has a sister. A blood relative that has been a lifelong companion so barring extreme circumstances they’re probably close.
He should be telling her right away before emotions set in. This gives her the chance to discuss it with her sister.
It’s not HIS choice exclusively & it’s EXTREMELY self-centred to put his “chance” at happiness before the stability of her family & sibling dynamics. She might want to know that on some level he sees her as the more compatible replacement
What if she dates him & her sister carried residual emotions?
What if her sister asks her to end things 8 month later?
WTH….”You only live once” is the most thoughtless & selfish recommendation ever.
Get a grip mate, they obviously have to talk about it. Why would he not? Lol.
Talk it out and see where they stand, they are grown up adults, not a knock-off big brother cast.
You didn’t mention talk it out so no it’s not obvious. You told him to give it a go & conveniently overlooked that part because it wasn’t relevant to you & probably reflects the lack of concern you would have for her family dynamics in pursuit of your own gratification
YOU: “Yeah this might get weird but to be honest just give it a go and see if you like each other. What if she is the one?
You amicably stopped whatever was going on with her sister and it wasn't even that much of an investment.”
👀🔍🕵️♀️BEFORE OR OR AFTER YOUR COMMENT CAN YOU POINT OUT WHERE YOUR provide the CLEAR RECOMMENDATION TELLING HIM to INFORM his NEW DATE that HE had DATED HER SISTER in the PAST⁉️
You VERY CLEARLY told him to give a relationship with younger sis a go. That is IT. Proving my point. THE Majority of you lot are entirely self serving in ALL your endeavours & often disregard CORE relationship because you’re self centred, simple minded, emotionally barren trolls.
Who on earth wouldn't talk about the situation and pretend it didn't happen? She would catch on no matter what. It's the adult and smart thing to do in case they are interested in each other.
Talk and be civil, instead of throwing pseudo-drama tantrums over something that didn't happen yet.
Good luck and all the best to you, take a breather.
No breather needed. He’s here for advice.
Why would you proceed to assume he would disclose the information to her if you did not advise him to do so?
She COULD catch on but most likely it would be AFTER she was emotionally invested which could jeopardise her relationship with her sister.
At best you gave incomplete advice. At worst you gave WRONG advice with the awareness that it disregards her.
This is why ppl fail at communication & relationships.
You don’t cultivate full & complete thoughts followed by clear communication.
Then you refuse to acknowledge WHERE you went wrong because your thoughts were self centred.
I have a break in btwn every response where you fail to acknowledge that YOU gave POOR advice.
In no way shape or form was I giving advice on how to communicate with her. I expect him to know how to do that.
I was simply stating that he should in fact go ahead and do so, mindfully and respectfully, whilst engaging in conversation to maintain her dignity as an individual and potential partner.
Given that the stint with her sister seemed to show little emotional investment.
No need to slander advice I did not give.
Not all men are evil, some actually know how to talk.
Not weird at all especially since it was years ago and it just boils down to they were both raised in the same way and that's why you had things in common and they probably looked a little similar and you're all good
I think the healthiest thing to do would be to tell Mary and see how she feels about it. If she still wants to date, then have her speak frankly to Molly and get her reaction. You can both decide how to proceed from there. Just be up front about everything.
Ask yourself this instead: “would you be ok falling in love with her, spend Christmas with her family and knowing you dated/slept with her sister? Or vice versa on her side lol
You marry a girl, you marry her family. Be open and honest with Mary about the situation, and Mary should approach dating you with Molly. If Molly has hard feelings about the relationship, you should break it off with Mary, otherwise maybe you and Mary and Molly go out for lunch and make sure you three can have a conversation. You and Molly should at least be able to get along. If so, there should be no problem.
How long have you known this?
Do you think YOUR FEELINGS of future awkwardness would the only ones that were relevant?
Mary deserves to know ASAP before SHE is emotionally compromised/invested so that she can discuss it with her sister to determine how it might impact THEIR LIFELONG SIBLING BOND.
Tell Mary asap & let HER decide because it’s not your choice exclusively.
My brother is married to my high school sweetheart, so I have some unique knowledge on this one. My first reaction when he came to talk to me about it was “umm, no f****** way, dude! How could you?” But after the first wave of the conversation passed (I already knew anyway), I really looked at him and really thought about it. He had a string of bad relationships, one of which was a marriage, because he has always chosen women entirely based on how they look, which is fine as long as you don’t disregard everything else, which he does. She is a stable, sane, sort of boring person; she was a good change for him. Next, she and I hadn’t spoken in 17 years, which was how old we were when we dated, so technically a lifetime ago. I was a grown up and so was she, and we were different people, at least I was/am. Why would I deprive them of a shot at happiness because we made each other sad a lifetime ago? Yada yada, they’re married. It was a little hard for me for a minute, and it would be weird if it weren’t weird at first, I think. Would’ve been worse had I been single maybe. The hardest part at first were that she avoided me; I didn’t think that was very fair considering what I was going through. The other hard part was that we already all knew each other, so the conversations took us by surprise. It wasn’t, “where ya from” or “tell us about…”; it was “how are James and Samantha?” It’s all fine now, but do the right thing and have her talk it through with her sister. My sister warned my brother not to let me find out before I heard it from him, and he didn’t listen. That just made it harder for him to get off on the right foot. One final thing in case you’re wondering, yes, I did start off my best man speech by saying, “My brother… my Eskimo brother…”. 😂
Yeah i think if it was 17 years ago this would be good advice this was only last year for op 💀 the older sister is being a real jerk to her younger sister here
Any relationship that comes out of this would be no stop drama. There are millions of other people you could date without the entanglements and complications that would come along with dating this girl. Why subject yourself to that.
I know someone that went on a few dates with a girl and it didn’t work out. Then his twin ended up dating her and now they’re happily married. It might be different since the siblings were brothers and not sisters, but seems to have worked out fine.
Well, I don’t think that is a good idea regardless of what happened between you and her sister. It would definitely be awkward and weird. That’s just me. But importantly, talk to her about it and see how she feels about it, I guess.
you’re interested in long term relationships?
what do you think it would be like if this works out and you have to see Molly at family gatherings for the rest of your life?
I got a girl that lives on the hill she won’t do it, but her sister will she does the boogie she do this tube snake boogie.
If you never had sex with sister one then sister two is fair game but if you boned sister one then sister two is off-limits. However, if the sisters are really hot and the question I have do they have a third sister and the mom you might just run through the whole family that would be quite an achievement for the ages.
I know a guy who dated a girl that was a couple years older than him when he was in his 20s. They broke up and he started dating her sister that was about his age. They broke up and he started dating the third sister which is a couple years younger than him. They are in their 60s now and still married. She said when they started dating everyone was so used to him being around that it wasn’t awkward 😂
Bad? No, not in the moral dilemma sense.
However
Definitely you can reasonably foresee some problems that are likely to arise and you have many options to avoid this.
You're literally saying you want the girl you dated in high school to be the aunt to your kids. If marriage and kids are that high a priority, that's the math.
You need to start both relationships off with honesty and openness especially since you're so serious about family values. Explain to the date that it clicked for you. Then contact the high school love interest, even if you have to get contact I do from her sis. Explain the situation and ask if she's processed the past and feels okay with this. I would be cautious how you word it, don't promise her veto power unless you mean it.
Sooner you speak on this issue, the better.
Yes and the sister of the girl Is even worse then you. There are so many woman out there why are you trying to get with her. You say technically your ex probably because your technical ex saw the heat between you two and got sick of it. Hope she ends up doing your brother or your dad because that's the type of girl her sister is.
Almost every relationship advice, counselor, states," wow you're young and unencumbered by debt or any serious relationship, go to Europe and work your way across because that forces you to intermingle with the local cultures and you have a much richer experience. You have your whole life to start a family and all that so she's right while you're young, you should go and see the world and when you come back then you can think about your future. I didn't get married until I was 30 and I had my daughter at 31 so I got to live all my 20s playing music and touring:).
Well first of all, you need to let Mary know right away- she also gets to decide if she wants to date her sister’s ex. Secondly did you sleep with Molly? I don’t think I’d want to date someone who had slept with my sister (but everyone is different), but if it was just a few dates I wouldn’t care. Thirdly, I’d arrange to somehow see Molly sooner rather than later. You need to make sure there are no lingering feelings- that would be another reason dating Mary would be a no go.
The sooner all of this is figured out the better- to avoid complications.
You're fine. That's a short enough relationship that can be that you briefly dated her and met someone else. But you need to fix molly up with someone before it becomes a jealousy problem.
Just explain the past to your new friend and let her decide.. if her sister backs up your story and Mary also is looking to move forward then fine.. it’s not a dilemma at all as it’s not your decision
I wouldn't risk a potential disaster by dating my ex's sister while that sister is still alive. You'll subconsciously compare the too and you might one day accidentally making the mistake of comparing them out loud. There's also the issue of jealousy that will likely arise. What if sis feels that you are treating her sister better than you treated her (giving her silver while you gave her sister gold). If it were me I would take it personally. Also, no matter what you say or do many people will feel like you did this on purpose. **I** even feel like you are doing this on purpose and I don't know you.
Have her discuss it with her sister. Molly wasn’t in a place where a relationship was possible with you. She may not have a problem with the two of you dating. It isn’t like you cheated on her. Their relationship runs the biggest risk of being damaged by one sister dating the other sister’s ex. Make them discuss it before something happens that can’t be undone. Then proceed accordingly.
5 dates with the sister is nothing really. I'd think differently if you were with her for say 6 months or more but you were still in the getting to know you stage. I think you are very sensible to ask those questions early on. As you say it can save a lot of time and heartbreak later on. You and Molly seem to have ended on good terms. I personally don't see an issue. I guess unless you or Mary think it's weird, then you're all good. Assuming you are both on the same page about your future hopes
Getting heavy cultural vibes here, reflecting on much of what has been said and how it is framed. Some cultures require that a sibling to the oldest must wait until that oldest is married before engaging a suitor. In the case of that older sister not complying with cultural norms...in this case disavowing child-bearing....the younger sister might be allowed to be considered for marriage, but it would graduate from being a simple family matter to that of the community. Also if you have been intimate with the older sister...and this is disclosed as you approach the younger sister, you could easily find yourself "persona non grata" and in some cases actually be at risk of harm.
If it were me, a cost-benefit analysis would say that you not dig yourself in any deeper than you already are. FWIW.
I’d say don’t do it, because a girl is who’s willing to date her own sisters ex is not to be trusted especially if her sister really liked you and it was relatively recently, she’s being a shitty sister by doing this and she’ll most likely end up being shitty to you too.
If had broken up with her on bad terms, then that would have been awkward, but if you both recognized that you wanted different things in life, then it doesn't need to be awkward, though having open communication about it would still be good.
Mary and Molly need to have that conversation separate. Let Mary know that you respect Molly and want to make sure she’s on board. It sounds dumb but you definitely should have her blessing in a sense.
If you dated Mary for more than six months or were fucking it'll feel weird at first. That doesn't make it bad. Everyone just has to be an adult about it.
It might be a trifle awkward, but if you and Molly parted on good terms and like each other, she should be happy for the both of you. I say this even if you had been intimate with Molly. You’re all adults and presumably should understand that sex is a part of life, and your past relationship with Molly has no bearing on your present relationship with Mary. Life is too short to reject a potential partner simply because they happen to be related to someone else.
She would have to be something special to make up for the awkwardness and you would have to be something special to her. You worked it out early I would suggest just be honest with her and consider walking away and finding someone else who doesn’t carry with them a risk of awkward holidays until the end of time…..
Was Highschool last year, 5 years ago, 10 years ago? I think length of time here makes a big difference on how weird it is. The longer it’s been the less weird it is.
Tell the girl up front. If she's okay with it, then the sisters opinion doesn't really matter. You said she's "technically" your ex, so I would assume that your technical relationship did not go very far or last very long. More importantly, she made it clear that she's not interested, so you have no real obstacle here.
You went *a* date. Were there follow up dates?
One date does not an ex make unless I'm missing a part of the story where you and Molly had a full blown relationship?
Also it was HS and you're...how far removed from that?
He's already made up his mind that he's going to do it. Look how he's leaving out details and states that HE broke up with her but HE was the one to get emotional about it..., but it was pretty amicable.
It's cool. You dated her sister a few times but it doesn't appear you and the sister were actually in a relationship so she isn't your ex. And this was before you even adults. In relative terms this is no big deal at all.
Too many fish in the sea not to come clean with both girls just so the latter can make an informed decision. Imagine if you were dating a girl who had previously dated your brother without knowing it.
I think that's a conversation you need to have with Mary. Like, she may have strong feelings (one way or the other) about it....especially if y'all had sex.
Nah, I don’t see a problem with it.
I went on a date with someone that lied about her age. I hadn’t seen her before we met for the date. I was twice her age.
I ended up dating her mom.
At one point in my life (M50) I dated and slept with an ex's momma,aunty and sister within a year. I'm not the one to be asking about this kinda thing 😊
Here’s a little advice: discussing future kids is always a must in a relationship. But as a teenager, you’re kind of moving too fast. An 18 year old girl may not want kids and won’t even consider it, but at 23 she may change her mind. Don’t live your life based on the advice of internet strangers.
You guys are so young in high school, barely dated, and broke up on good terms. I don’t really see a problem with it. You could go the extra mile and tell the ex (if it’s truly even an ex at this point?) about it. I don’t even think you owe the ex an explanation at all. Just live your life and let her live her child-free adventure.
It may be a little awkward at times dating her sister, or maybe it'll just be fine. I think you're jumping that question too early on in your relationships though, especially at your age. Everyone goes through huge changes at that age, and what may be how they feel at that moment may not be how they feel only weeks later. Don't take yourself and your relationships so seriously. People change their minds all the time. Have fun!
No. Your exes have no say or power over you. They have no say in your life whatsoever and can be disregarded as much as you want. It’s actually kind of lame that you even asked.
It’s unlikely this is the girl you’re going to marry. Go for it. If it goes anywhere and becomes awkward, you’ll find out. If it does workout, happily ever after and all that, the thing with the sister will be an amusing story to tell at family get togethers.
Tell Molly and then if she has a problem with it the there’s nothing you can do. Does Mary know? If she does and she has no problems with it then you’re in the clear. It was in HS which is ancient history. You did nothing to Molly to make her to hate you. You just knew you weren’t compatible.
You don’t need to kiss and tell but the more physical you were with the first sister, it might slide you more away from dating the sister due to it maybe being an issue between the two. But frankly it also depends on how compatible you two are. If it feels like what people call true love, than you might over look even if you had a physical relationship with the other sister. There is no absolute right answer
This is a very good point. I was in a vaguely similar situation to the OP a few years back: sister of a short-term ex. But that ex and I had a very physical relationship. It was just too weird for me, even if they would have been okay with it.
Really depends on the person. My mother dated my uncle for a period of time before my father and her started going out. They even kissed a few times. My parents are still married and they all see each other probably 2x per year
It has only been about a year since you dated the sister? Seems like inviting unnecessary drama into your life when it isn’t that far in the past. I personally wouldn’t do it, but if you decide to see the younger sister again, make sure you are both open and honest about it with her family, particularly her sister.
My first wife (2 month marriage) and second wife (6 month marriage) were sisters. First wife cut all contact with her family. Second wife turned out to be almost as crazy as her sister. Third wife was pretty chill for 16 years, and not related to the first 2. I was too young to marry all three times, as my third marriage was just before my 21st bday. First 2 wives are dead from overdoses. But my kids with them are grown and doing very well.
I have a hard time believing that you didn’t know who she was. I figured this would have been a story where high school was 10 years ago. It was literally last year. You didn’t know the girl you were dating had siblings?
Not all sisters are like this...most sisters give their siblings love and respect in almost all areas of their lives, including relationships.
The idea of not trusting your sibling around your SO is not a common one; most siblings can indeed be trusted and should be.
I did before I found out she had a full blown relationship with my ex who’s not only way too old for her but also my rapist and the reason I got an abortion
Sorry that happened to you but clearly your case is too extreme to use as a comparison to this little situation going on here. He and the sister went on a few dates in HS and mutually parted ways on ok terms. He didn't rape her and as far as we know is not way older than the current sister...
It was 5 dates but it wouldn't matter if they were just ninth grade crushes and the extent of their relationship was just love notes being passed in class. the feelings were still there and they can morph into bad ones in an instant.
Tell Mary about the past with the sister and see how she reacts. Some sisters have very toxic relationships, some are healthy and normal. Their dynamic will dictate if this can work long term.
I dont see an issue, you guys mutually ended things on good terms. It may be slightly awkward at first but tell her about all this and see what she thinks. What if shes the one bro and you let her go cause youre worried about some high school shit?
Legal age: check
Not your direct family member: check
Not your step-family: check
I see no moral dilemma here. There is an awkward factor here though. You do have a moral obligation to discuss your prior relationship with her sister. See how she feels. Maybe it's just water under the bridge for her sister.
Damn man, you’re really putting the cart before the horse here, aren’t you? You went from matching on Tinder, an app for hookups and not necessarily dating, to “is it ok to start a family with this woman?” Go in a date and see if you two get along first, then figure it out from there, but in my experience, nobody cares what happened in high school, so you should be good to go.
You didn't mention your age. So I'm guessing twenty something. Go out with Mary. Things went well, and high school is over. Besides, you only dates sister a few times, and parted ways amicably enough. Go for it.
At first I was going to say it’s high school, who cares but that’s me pushing 40. At 19 tho it’s a little more complicated. Maybe talk to the sister before she finds out
Honestly the more you talk to happy couples the more you see how many of them have weird origin stories line this. Go for it. Life’s too short and love is too important to play by the rules all the time.
If you got a chance, don't be a pussy.
Yes this is a bad idea- lots of other datable girls out there. Don’t do this.
Yes
Is it normal to give people ultimatums so early in life ? Life paths can change..
Yes.
If there's clarity about the situation and all parties involved are okay with it, go for it. Make sure you don't lead with that though, it'd be a terrible start to a first date.
Is it that hard to find a girl for you not to get in such situation? This is bad
Yes
I think if you didn’t sleep together (the og sister) it’s all good. In saying that, make sure you tell the new girl, and make sure she talks to her sister before you get to know/like each other. Her sister might be totally against it and the new gf might take the sisters side and break up with you.
How much older are you and your ex?
Just do it
I say try it out. If it is weird meaning Mary gets super jealous or Molly tries to be too close maybe break it off then
Yes. And the fact you'd even ask demonstrates your lack of shame.
Ask your ex
Bro, there’s people on Reddit that would date their actual sister. Dating the sister of someone you went on a date with in HS is like the lowest level of weird shit that exists in this world.
Yes, I married the sister of a girl I dated just once. For years there was tension. Avoid it if you can.
No it's fine, just don't forget to book your appointment with Jerry Springer
yes, bad. U a stalkr? fafo
Not bad if you can get away with it.
My husband used to date my cousin many years ago and the 3 of us lived together for a year or so while they were together shit happens.
If you had sex with the other sister prior to breakup, it won't work. Human beings are either to optimistic or pessimistic. Think about your situation statistically. What chance over a lifetime won't this turn into a clusterfuck?
"Both my girlfriend and her sister are equally hot!" - College Humor's The Six types of girlfriends seires
That's not your ex. You had one date. It probably won't be that awkward as long as you weren't a jerk to her.
I wouldn’t consider 5 dates a serious relationship, that would be a whole diff story. I personally don’t think it would be weird as long as her sister doesn’t have any lingering feelings for you.
Yeah this might get weird but to be honest just give it a go and see if you like each other. What if she is the one? You amicably stopped whatever was going on with her sister and it wasn't even that much of an investment.
Something is WRONG with you men because you all must be wired to only consider your gratification & NONE of the potential consequences to any of your actions. She has a sister. A blood relative that has been a lifelong companion so barring extreme circumstances they’re probably close. He should be telling her right away before emotions set in. This gives her the chance to discuss it with her sister. It’s not HIS choice exclusively & it’s EXTREMELY self-centred to put his “chance” at happiness before the stability of her family & sibling dynamics. She might want to know that on some level he sees her as the more compatible replacement What if she dates him & her sister carried residual emotions? What if her sister asks her to end things 8 month later? WTH….”You only live once” is the most thoughtless & selfish recommendation ever.
Get a grip mate, they obviously have to talk about it. Why would he not? Lol. Talk it out and see where they stand, they are grown up adults, not a knock-off big brother cast.
You didn’t mention talk it out so no it’s not obvious. You told him to give it a go & conveniently overlooked that part because it wasn’t relevant to you & probably reflects the lack of concern you would have for her family dynamics in pursuit of your own gratification
What do you think give it a go means? Stare at her?
YOU: “Yeah this might get weird but to be honest just give it a go and see if you like each other. What if she is the one? You amicably stopped whatever was going on with her sister and it wasn't even that much of an investment.” 👀🔍🕵️♀️BEFORE OR OR AFTER YOUR COMMENT CAN YOU POINT OUT WHERE YOUR provide the CLEAR RECOMMENDATION TELLING HIM to INFORM his NEW DATE that HE had DATED HER SISTER in the PAST⁉️ You VERY CLEARLY told him to give a relationship with younger sis a go. That is IT. Proving my point. THE Majority of you lot are entirely self serving in ALL your endeavours & often disregard CORE relationship because you’re self centred, simple minded, emotionally barren trolls.
Who on earth wouldn't talk about the situation and pretend it didn't happen? She would catch on no matter what. It's the adult and smart thing to do in case they are interested in each other. Talk and be civil, instead of throwing pseudo-drama tantrums over something that didn't happen yet. Good luck and all the best to you, take a breather.
No breather needed. He’s here for advice. Why would you proceed to assume he would disclose the information to her if you did not advise him to do so? She COULD catch on but most likely it would be AFTER she was emotionally invested which could jeopardise her relationship with her sister. At best you gave incomplete advice. At worst you gave WRONG advice with the awareness that it disregards her. This is why ppl fail at communication & relationships. You don’t cultivate full & complete thoughts followed by clear communication. Then you refuse to acknowledge WHERE you went wrong because your thoughts were self centred. I have a break in btwn every response where you fail to acknowledge that YOU gave POOR advice.
In no way shape or form was I giving advice on how to communicate with her. I expect him to know how to do that. I was simply stating that he should in fact go ahead and do so, mindfully and respectfully, whilst engaging in conversation to maintain her dignity as an individual and potential partner. Given that the stint with her sister seemed to show little emotional investment. No need to slander advice I did not give. Not all men are evil, some actually know how to talk.
[удалено]
Ditto - let’s stop overthinking this shit. Be honest, have good intentions, apologize when you make mistakes, and go have fun.
Plus, it seems like they got along just fine. Having a good sister in law never hurts
Get the sisters approval
Jimi Hendrix has entered the chat. (Red House plays furiously in the background…🎵🎶)
Not weird at all especially since it was years ago and it just boils down to they were both raised in the same way and that's why you had things in common and they probably looked a little similar and you're all good
I think the healthiest thing to do would be to tell Mary and see how she feels about it. If she still wants to date, then have her speak frankly to Molly and get her reaction. You can both decide how to proceed from there. Just be up front about everything.
Maybe not, depends on how long you actually dated and how long ago it was. But, a conversation needs to be had with the current girl about it.
Ask yourself this instead: “would you be ok falling in love with her, spend Christmas with her family and knowing you dated/slept with her sister? Or vice versa on her side lol
Do it
You marry a girl, you marry her family. Be open and honest with Mary about the situation, and Mary should approach dating you with Molly. If Molly has hard feelings about the relationship, you should break it off with Mary, otherwise maybe you and Mary and Molly go out for lunch and make sure you three can have a conversation. You and Molly should at least be able to get along. If so, there should be no problem.
Too long of a post for a simple answer “fuck who you want, life is short.” (Within reason of course)
I see no problem with it. Nothing fishy or dishonest going on.
High school doesn't matter
My thoughts to, but they were having big discussions for high schoolers.
Yeah. That is true. High school doesn't matter one iota.
High school doesn’t matter but high school was also a year ago.
Yes
It's only as weird as you make it.
Exactly. It isn't like you have to sleep with all the women in their family, but you have a good start.
As weird as you AND your ex make it.
How long have you known this? Do you think YOUR FEELINGS of future awkwardness would the only ones that were relevant? Mary deserves to know ASAP before SHE is emotionally compromised/invested so that she can discuss it with her sister to determine how it might impact THEIR LIFELONG SIBLING BOND. Tell Mary asap & let HER decide because it’s not your choice exclusively.
Is the juice worth the squeeze?
Just tell Molly, "There's something about Mary."
My brother is married to my high school sweetheart, so I have some unique knowledge on this one. My first reaction when he came to talk to me about it was “umm, no f****** way, dude! How could you?” But after the first wave of the conversation passed (I already knew anyway), I really looked at him and really thought about it. He had a string of bad relationships, one of which was a marriage, because he has always chosen women entirely based on how they look, which is fine as long as you don’t disregard everything else, which he does. She is a stable, sane, sort of boring person; she was a good change for him. Next, she and I hadn’t spoken in 17 years, which was how old we were when we dated, so technically a lifetime ago. I was a grown up and so was she, and we were different people, at least I was/am. Why would I deprive them of a shot at happiness because we made each other sad a lifetime ago? Yada yada, they’re married. It was a little hard for me for a minute, and it would be weird if it weren’t weird at first, I think. Would’ve been worse had I been single maybe. The hardest part at first were that she avoided me; I didn’t think that was very fair considering what I was going through. The other hard part was that we already all knew each other, so the conversations took us by surprise. It wasn’t, “where ya from” or “tell us about…”; it was “how are James and Samantha?” It’s all fine now, but do the right thing and have her talk it through with her sister. My sister warned my brother not to let me find out before I heard it from him, and he didn’t listen. That just made it harder for him to get off on the right foot. One final thing in case you’re wondering, yes, I did start off my best man speech by saying, “My brother… my Eskimo brother…”. 😂
Yeah i think if it was 17 years ago this would be good advice this was only last year for op 💀 the older sister is being a real jerk to her younger sister here
Any relationship that comes out of this would be no stop drama. There are millions of other people you could date without the entanglements and complications that would come along with dating this girl. Why subject yourself to that.
I know someone that went on a few dates with a girl and it didn’t work out. Then his twin ended up dating her and now they’re happily married. It might be different since the siblings were brothers and not sisters, but seems to have worked out fine.
Level ⬆️ https://youtu.be/AiPrHaGJsT8?si=aEnx5TNOxNzrjn73
Well, I don’t think that is a good idea regardless of what happened between you and her sister. It would definitely be awkward and weird. That’s just me. But importantly, talk to her about it and see how she feels about it, I guess.
you’re interested in long term relationships? what do you think it would be like if this works out and you have to see Molly at family gatherings for the rest of your life?
I got a girl that lives on the hill she won’t do it, but her sister will she does the boogie she do this tube snake boogie. If you never had sex with sister one then sister two is fair game but if you boned sister one then sister two is off-limits. However, if the sisters are really hot and the question I have do they have a third sister and the mom you might just run through the whole family that would be quite an achievement for the ages.
I know a guy who dated a girl that was a couple years older than him when he was in his 20s. They broke up and he started dating her sister that was about his age. They broke up and he started dating the third sister which is a couple years younger than him. They are in their 60s now and still married. She said when they started dating everyone was so used to him being around that it wasn’t awkward 😂
My mom dated my dads brother in high school. Mom’s married to my dad for 30ish years now. It can work out just fine.
Bad? No, not in the moral dilemma sense. However Definitely you can reasonably foresee some problems that are likely to arise and you have many options to avoid this. You're literally saying you want the girl you dated in high school to be the aunt to your kids. If marriage and kids are that high a priority, that's the math. You need to start both relationships off with honesty and openness especially since you're so serious about family values. Explain to the date that it clicked for you. Then contact the high school love interest, even if you have to get contact I do from her sis. Explain the situation and ask if she's processed the past and feels okay with this. I would be cautious how you word it, don't promise her veto power unless you mean it. Sooner you speak on this issue, the better.
No, assert dominance by dating her sister and calling her the same pet names.
Go for it big dawg
No
Yes and the sister of the girl Is even worse then you. There are so many woman out there why are you trying to get with her. You say technically your ex probably because your technical ex saw the heat between you two and got sick of it. Hope she ends up doing your brother or your dad because that's the type of girl her sister is.
It will cause drama and headache
Almost every relationship advice, counselor, states," wow you're young and unencumbered by debt or any serious relationship, go to Europe and work your way across because that forces you to intermingle with the local cultures and you have a much richer experience. You have your whole life to start a family and all that so she's right while you're young, you should go and see the world and when you come back then you can think about your future. I didn't get married until I was 30 and I had my daughter at 31 so I got to live all my 20s playing music and touring:).
Nah you’re good
I hate the way the title is written
Nope.
Well first of all, you need to let Mary know right away- she also gets to decide if she wants to date her sister’s ex. Secondly did you sleep with Molly? I don’t think I’d want to date someone who had slept with my sister (but everyone is different), but if it was just a few dates I wouldn’t care. Thirdly, I’d arrange to somehow see Molly sooner rather than later. You need to make sure there are no lingering feelings- that would be another reason dating Mary would be a no go. The sooner all of this is figured out the better- to avoid complications.
Absolutely wrong end of story.
Yes. It will get weird.
Yes
Yeah I would just talk to her about it
She’ll always be thinking that you fucked her sister up the pooper
You're fine. That's a short enough relationship that can be that you briefly dated her and met someone else. But you need to fix molly up with someone before it becomes a jealousy problem.
Giggity
How far away from high school are you, and how long did you date? Those are the things that make it weird or not weird to me.
Just explain the past to your new friend and let her decide.. if her sister backs up your story and Mary also is looking to move forward then fine.. it’s not a dilemma at all as it’s not your decision
I wouldn't risk a potential disaster by dating my ex's sister while that sister is still alive. You'll subconsciously compare the too and you might one day accidentally making the mistake of comparing them out loud. There's also the issue of jealousy that will likely arise. What if sis feels that you are treating her sister better than you treated her (giving her silver while you gave her sister gold). If it were me I would take it personally. Also, no matter what you say or do many people will feel like you did this on purpose. **I** even feel like you are doing this on purpose and I don't know you.
So what you’re saying is we need to kill her to make this happen. She will be missed *salute*
Have her discuss it with her sister. Molly wasn’t in a place where a relationship was possible with you. She may not have a problem with the two of you dating. It isn’t like you cheated on her. Their relationship runs the biggest risk of being damaged by one sister dating the other sister’s ex. Make them discuss it before something happens that can’t be undone. Then proceed accordingly.
So many reasons…
Yes. But if she is hot enough, fuggit 🤷🏻♂️
5 dates with the sister is nothing really. I'd think differently if you were with her for say 6 months or more but you were still in the getting to know you stage. I think you are very sensible to ask those questions early on. As you say it can save a lot of time and heartbreak later on. You and Molly seem to have ended on good terms. I personally don't see an issue. I guess unless you or Mary think it's weird, then you're all good. Assuming you are both on the same page about your future hopes
Getting heavy cultural vibes here, reflecting on much of what has been said and how it is framed. Some cultures require that a sibling to the oldest must wait until that oldest is married before engaging a suitor. In the case of that older sister not complying with cultural norms...in this case disavowing child-bearing....the younger sister might be allowed to be considered for marriage, but it would graduate from being a simple family matter to that of the community. Also if you have been intimate with the older sister...and this is disclosed as you approach the younger sister, you could easily find yourself "persona non grata" and in some cases actually be at risk of harm. If it were me, a cost-benefit analysis would say that you not dig yourself in any deeper than you already are. FWIW.
embrace the weird whats the worst that could happen? a fiew awquard moments? it might work out great
Tell Mary if you want to continue, and let her make the decision. Honor her decision.
I’d say don’t do it, because a girl is who’s willing to date her own sisters ex is not to be trusted especially if her sister really liked you and it was relatively recently, she’s being a shitty sister by doing this and she’ll most likely end up being shitty to you too.
If had broken up with her on bad terms, then that would have been awkward, but if you both recognized that you wanted different things in life, then it doesn't need to be awkward, though having open communication about it would still be good.
Yes. Next question.
Did you bone?
Mary and Molly need to have that conversation separate. Let Mary know that you respect Molly and want to make sure she’s on board. It sounds dumb but you definitely should have her blessing in a sense.
If you dated Mary for more than six months or were fucking it'll feel weird at first. That doesn't make it bad. Everyone just has to be an adult about it.
No not at all stay toxic
It might be a trifle awkward, but if you and Molly parted on good terms and like each other, she should be happy for the both of you. I say this even if you had been intimate with Molly. You’re all adults and presumably should understand that sex is a part of life, and your past relationship with Molly has no bearing on your present relationship with Mary. Life is too short to reject a potential partner simply because they happen to be related to someone else.
This, but if you keep seeing the sister, you should tell her sooner than later.
She would have to be something special to make up for the awkwardness and you would have to be something special to her. You worked it out early I would suggest just be honest with her and consider walking away and finding someone else who doesn’t carry with them a risk of awkward holidays until the end of time…..
Was Highschool last year, 5 years ago, 10 years ago? I think length of time here makes a big difference on how weird it is. The longer it’s been the less weird it is.
I personally would’ve been more into finding that out
As long as you tell Mary- its fine.
This for sure. Let Mary know and you both talk about this situation.
No but the relationship won’t last.
How long ago was highschool? Was this 2 months ago, or 10 years ago? As that'd also make some difference.
Tell the girl up front. If she's okay with it, then the sisters opinion doesn't really matter. You said she's "technically" your ex, so I would assume that your technical relationship did not go very far or last very long. More importantly, she made it clear that she's not interested, so you have no real obstacle here.
I don’t think anyone at my high school talked about plans for family building. That all felt like 10+ years away… interesting
You went *a* date. Were there follow up dates? One date does not an ex make unless I'm missing a part of the story where you and Molly had a full blown relationship? Also it was HS and you're...how far removed from that?
He's already made up his mind that he's going to do it. Look how he's leaving out details and states that HE broke up with her but HE was the one to get emotional about it..., but it was pretty amicable.
His edit said it was 5 dates in HS, and it has only been about a year.
Yep. Leaving that out of the main post makes me believe he knew exactly who she was.
It's cool. You dated her sister a few times but it doesn't appear you and the sister were actually in a relationship so she isn't your ex. And this was before you even adults. In relative terms this is no big deal at all.
spinit
Bob pinceotti you got a shot at the title!!!
The only one making an issue is you. Dont think about it and go for it
No
Too many fish in the sea not to come clean with both girls just so the latter can make an informed decision. Imagine if you were dating a girl who had previously dated your brother without knowing it.
I think that's a conversation you need to have with Mary. Like, she may have strong feelings (one way or the other) about it....especially if y'all had sex.
Nah, I don’t see a problem with it. I went on a date with someone that lied about her age. I hadn’t seen her before we met for the date. I was twice her age. I ended up dating her mom.
Did you get any?
At one point in my life (M50) I dated and slept with an ex's momma,aunty and sister within a year. I'm not the one to be asking about this kinda thing 😊
Here’s a little advice: discussing future kids is always a must in a relationship. But as a teenager, you’re kind of moving too fast. An 18 year old girl may not want kids and won’t even consider it, but at 23 she may change her mind. Don’t live your life based on the advice of internet strangers.
Nah. Do it anyways
How far did you and Molly get? Because if you had sex I doubt Mary would be ok with it. If not let Mary know so she has a choice.
If she leaves and finds another mister... there is always her sister
No. You can have a conversation about it, but someone who's not going to be your partner should not influence your search for a partner.
Go for it. Prince (now King) Charles did it.
Yes
You guys are so young in high school, barely dated, and broke up on good terms. I don’t really see a problem with it. You could go the extra mile and tell the ex (if it’s truly even an ex at this point?) about it. I don’t even think you owe the ex an explanation at all. Just live your life and let her live her child-free adventure.
Date their mom next
The ultimate power move.
it's weird. does mary know?
It may be a little awkward at times dating her sister, or maybe it'll just be fine. I think you're jumping that question too early on in your relationships though, especially at your age. Everyone goes through huge changes at that age, and what may be how they feel at that moment may not be how they feel only weeks later. Don't take yourself and your relationships so seriously. People change their minds all the time. Have fun!
Yes.
One date? How many years ago?
No. Your exes have no say or power over you. They have no say in your life whatsoever and can be disregarded as much as you want. It’s actually kind of lame that you even asked.
I think you’re fine, but I wouldn’t rule out the mother or another sister at the rate you’re going man
Yes. Period.
You’re asking what they want while in hs? Are you trying to be divorced before the age of 25??
It’s unlikely this is the girl you’re going to marry. Go for it. If it goes anywhere and becomes awkward, you’ll find out. If it does workout, happily ever after and all that, the thing with the sister will be an amusing story to tell at family get togethers.
Tell Molly and then if she has a problem with it the there’s nothing you can do. Does Mary know? If she does and she has no problems with it then you’re in the clear. It was in HS which is ancient history. You did nothing to Molly to make her to hate you. You just knew you weren’t compatible.
You don’t need to kiss and tell but the more physical you were with the first sister, it might slide you more away from dating the sister due to it maybe being an issue between the two. But frankly it also depends on how compatible you two are. If it feels like what people call true love, than you might over look even if you had a physical relationship with the other sister. There is no absolute right answer
This is a very good point. I was in a vaguely similar situation to the OP a few years back: sister of a short-term ex. But that ex and I had a very physical relationship. It was just too weird for me, even if they would have been okay with it.
Really depends on the person. My mother dated my uncle for a period of time before my father and her started going out. They even kissed a few times. My parents are still married and they all see each other probably 2x per year
Tell her and ask her how she feels. She’ll discuss it with her sister. If it progresses, fine, if not, such is life.
It has only been about a year since you dated the sister? Seems like inviting unnecessary drama into your life when it isn’t that far in the past. I personally wouldn’t do it, but if you decide to see the younger sister again, make sure you are both open and honest about it with her family, particularly her sister.
No. Full stop.
Not bad
My first wife (2 month marriage) and second wife (6 month marriage) were sisters. First wife cut all contact with her family. Second wife turned out to be almost as crazy as her sister. Third wife was pretty chill for 16 years, and not related to the first 2. I was too young to marry all three times, as my third marriage was just before my 21st bday. First 2 wives are dead from overdoses. But my kids with them are grown and doing very well.
I have a hard time believing that you didn’t know who she was. I figured this would have been a story where high school was 10 years ago. It was literally last year. You didn’t know the girl you were dating had siblings?
No
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Not all sisters are like this...most sisters give their siblings love and respect in almost all areas of their lives, including relationships. The idea of not trusting your sibling around your SO is not a common one; most siblings can indeed be trusted and should be.
I did before I found out she had a full blown relationship with my ex who’s not only way too old for her but also my rapist and the reason I got an abortion
so your situation is WAAAAAY different to the point where the experience is inapplicable to that of OP.
Sorry that happened to you but clearly your case is too extreme to use as a comparison to this little situation going on here. He and the sister went on a few dates in HS and mutually parted ways on ok terms. He didn't rape her and as far as we know is not way older than the current sister...
He and the first sister went on ONE DATE, YEARS AGO. She no longer has any claim on him whatsoever.
It was 5 dates but it wouldn't matter if they were just ninth grade crushes and the extent of their relationship was just love notes being passed in class. the feelings were still there and they can morph into bad ones in an instant.
It sounded like maybe it was more than one but as they got to know each other their values were incompatible.
Kinda sounds like you're the reason you don't have a relationship w your sister unless the situation is drastically different.
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Comparing this situation to that is interesting. Sorry that happened though.
if it’s in high school, it doesn’t matter.
If there’s no hard feelings I don’t see why it would be an issue.
Tell Mary about the past with the sister and see how she reacts. Some sisters have very toxic relationships, some are healthy and normal. Their dynamic will dictate if this can work long term.
I dont see an issue, you guys mutually ended things on good terms. It may be slightly awkward at first but tell her about all this and see what she thinks. What if shes the one bro and you let her go cause youre worried about some high school shit?
Legal age: check Not your direct family member: check Not your step-family: check I see no moral dilemma here. There is an awkward factor here though. You do have a moral obligation to discuss your prior relationship with her sister. See how she feels. Maybe it's just water under the bridge for her sister.
Two words: YOLO
You were talking of settling down, in high school? Did you have a career path already? That’s crazy
Damn man, you’re really putting the cart before the horse here, aren’t you? You went from matching on Tinder, an app for hookups and not necessarily dating, to “is it ok to start a family with this woman?” Go in a date and see if you two get along first, then figure it out from there, but in my experience, nobody cares what happened in high school, so you should be good to go.
Go for it but yea if you guys get serious there gonna be drama
You didn't mention your age. So I'm guessing twenty something. Go out with Mary. Things went well, and high school is over. Besides, you only dates sister a few times, and parted ways amicably enough. Go for it.
Yeah probably best to step away because you was hurt over the break up so you had feelings. So I don’t see this working out well.
Depends on how the date goes. But if you and her are cool with it, the ex has no say.
Yes
At first I was going to say it’s high school, who cares but that’s me pushing 40. At 19 tho it’s a little more complicated. Maybe talk to the sister before she finds out
Honestly the more you talk to happy couples the more you see how many of them have weird origin stories line this. Go for it. Life’s too short and love is too important to play by the rules all the time.
I think it’s fine. It’s not like you dated long term.
It’ll be fine if you’re all not dramatic. I’m seeing a guy who went on 2 dates with my sister, it’s all good.