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Anonymous asked in Family & RelationshipsSingles & Dating · 2 months ago

Would it be weird to date someone your sister hooked up with 5 years ago?

A guy that I recently met and have alot in common with asked me out on a date. But he had hooked up with my older sister 5 years ago. They weren't boyfriend and girlfriend. Just had a short fling that didn't end well. My sister has a reputation of sleeping around and has been known as a Maneater lol. She's married now but she still has issues and has always been  shady to people and family members. We are not super close but I still love her and we talk sometimes. What should I do? He's a good guy but I want to vomit thinking about them hooking up. He says he doesn't even remember it and I'm just making it weird.

3 Answers

  • 2 months ago

    Not sure why you're living in your sister's and this guy's sexual pasts.  live right now and you can make a more sound decision, which would have nothing to do with your sister.  Your decisions are about YOU.

  • 2 months ago

    In short yes, your sister may not appreciate it. There is a reason why he is her ex and she probably doesn't want to have anything to do with him so by you dating him you are re-introducing something she doesn't want. Kind of shows that you don't care about her feelings no matter how much you like him.

  • Anonymous
    2 months ago

    It's weird if you make it weird? No, it's weird, and there's nothing weird about you thinking it's weird. The opposite. It's totally normal for you to think it's weird. Why? BECAUSE IT'S WEIRD! There's nothing wrong with weird, but let's call a spade a spade and not pretend that it's not weird and just you "making it weird." The larger issue is if you can't handle that he hooked up with your sister, if it weirds you out, if it makes you "want to vomit," then you need to give these feelings of yours serious consideration and not just shove them down because you're being shamed into doing so by being told that you're "making it weird." 

    Why give it serious consideration? Well, they're your feelings and so are worth your serious consideration. Also, extend those feelings beyond today into the future. Say, for the sake of discussion, you and he become an actual thing, a major relationship, one that goes on for months or years or maybe even ends up with you and he wanting to get married or even getting married, you will forever have your sister lording over you that she had him first and threw him out, that you got her sloppy seconds, that she's had her hands all over your man, that she remembers exactly what his penis was like and remembers feeling it inside her, blah, blah, blah. Based on everything you've said about her, she'll do that even if she doesn't remember having sex with him and will definitely say she does, but somebody has to remember it if your boyfriend doesn't remember it for you to know about it, so she probably actually DOES remember it, meaning she'll be able to slam you with accurate descriptions of his body, of things he does, of sounds he makes, etc., and it'll cut so deep that your expression will betray the truth of it, because you know that his body is like she says, that those are things he does, that those are sounds he makes from you having sex with him, and when she sees it slam you like that, she'll know she's hit a nerve and say it again and again, say it in front of friends and family to mortify you and to your face and behind your back, all the while laughing and playing it off as just fun teasing as you try to pretend it is too because you don't want to give her the satisfaction, but she and you both know she's digging away at you, throwing shade.

    I guarantee—GUARANTEE—that's what will happen. No question. So if you can't handle it now, if it makes you want to vomit now, how will you ever be able to handle it, keep it from making you vomit, and not let it drive you absolutely crazy when your this sister you love but is super shady really cranks up the heat and just never lets you forget it? A maneater who has a reputation and sleeps around is the black sheep and she's going to do everything in her power to constantly knock you down, and she's going to do that by lording this over you.

    So decide now— Can you handle it? Can you picture yourself being able to deal with your sister making it a thing every time she sees you that she screwed your boyfriend and didn't think he was worth keeping and in the process getting into sordid details about him, sexually graphic descriptions meant to really get under your skin?

    Some people can handle that and would just tell their sister to fvck off. To me, you don't sound like you're one of those people. So you need to think about that before getting in too deep with this guy, because contrary to every sappy movie ever made, there isn't just one guy out there for you. You can decide that the sexual baggage he brings having had sex with your sister is more than you want to carry, especially knowing that your sister is going to load that baggage onto you at every opportunity and you're going to be carrying it a lot for a very long time and it's going to get very, very heavy, and deciding that is totally OK and not at all weird.

    I mean, I understand why your boyfriend is trying to downplay it, because he sees he's got a good thing going with you, but at the same time I don't agree with it and it throws up a couple of red flags about him and your relationship with him:

    One red flag is he's not empathizing with you at all. He's acting like your weird for by making it weird when you're not being weird or making it weird but are totally normal, are having a totally understandable reaction. Him having had sex with your sister actually IS weird, by anyone's standards, so you being weirded out by it is something he should completely get, not something he should treat like you're having this overblown, out-there, reaction, not like you're the one "making it weird." And I feel like he does get that it's weird, but he's pretending like you're the one making it weird so that he doesn't have to deal with his past and its effect on you but puts the onus entirely on you to deal with it silently on your own, even coercing you to stifle your feelings by making you feel embarrassed for having them, embarrassed for "making it weird," embarrassed to bring it up, so you're stuck dealing with it on your own in silence while he doesn't have to deal with his past at all, because now for him by making you feel this way, it's out of sight, out of mind. 

    A second red flag is he's lying about not remembering having sex with your sister. I'm a guy. I lost my virginity six years ago, and since then, I've had sex with about a hundred girls. I remember each one. I mean, I don't remember all their names or everything they ever told me, but if you point a girl out to me that I've had sex with, I'll remember her, remember having sex with her, and be able to sensorially remember aspects of having sex with her, her body, the way she smelled, how her boobs felt, etc. Sex is huge to guys. It's not something guys forget, not even one night stands, not even when guys have had a lot of one night stands. Guys make a point of turning on a video recorder in their brain when they have sex and commit as much as they can to memory because guys very much want to be able to remember it later, maybe not so much when it's someone they've come to routinely have sex with but DEFINITELY when it's a one-off or a first time, what with not ever really knowing if a first time is going to lead to more times or be the only time. So there's no ifs, ands, or buts about it— your boyfriend is lying about not remembering having sex with your sister. And, yes, as guys do, as I admittedly do, he will stick to that lie to his dying breath, but that doesn't make it not a lie.

    Frankly, it would be a lot more encouraging if he showed you some empathy by showing you he totally gets how you'd think that's weird instead of doing the opposite and making you feel like it's really not weird but you're the weirdo making it weird. It would also be a lot more encouraging if he just honestly admitted remembering having sex with your sister. How are you supposed to start a relationship on such dishonest? What kind of basis is that? And if he were honest, he could lay everything out on the table about what he remembers, which while maybe difficult to here, will earn him your trust and prepare you for whatever your sister might say so that you're not hit with something out of left field.

    I mean, he's totally lying about not remembering. If he really doesn't remember and your sister is such a ho that she'd never remember, certainly way more of a ho thane he is, then how did it even come up that he had sex with your sister? If your sister brought it up, then how is it that she remembers having sex with him 5 years ago when she's had sex with way more people than him but he doesn't? I'm not buying it. That doesn't make sense, especially considering how guys are about sex, how guys find it way more memorable than girls do, and not just to be able to play it back in memory but also because for guys, all guys in our society, sex is an achievement, an esteem builder, something to be counted and remembered, the more, the better, unlike with girls in our society where sex is often used as an esteem destroyer, something not to be counted or remembered because the more, the worse, because that's how girls get reputations— guys studs, girls hos. If it doesn't make sense, it's almost never true. There's just no way in hell he doesn't remember having sex with your sister, especially when your sister does, which she must, because if he doesn't remember it, you can't have found out about it from him, so you must have found out about it from her, for if not from her or him, who? So not only is he making you out to be the weirdo for having an issue with him having had sex with your sister instead of empathizing with your totally understandable reaction, he's also lying instead of owning up, being honest, and dealing with you honestly.

    I dunno. With all that in mind, I think I'd move on from him if I were you. His big red flags this early on plus the how your sister is going to lord her having had sex with your boyfriend and then tossing him aside over you the whole time you're with him and probably even long after you're no longer with him equals NOT WORTH IT! That's just my humble opinion.  

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