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Not long before we started to date he had sex with a girl who is one of my friends. Now I know I feel uncomfortable about it. How should I respond?

Tagged as: Dating, Friends, Sex, Trust issues<< Previous question   Next question >>
Question - (8 June 2016) 12 Answers - (Newest, 13 June 2016)
A female United States age 30-35, anonymous writes:

Would you date a guy who had slept with your friend not long before you decided to date? Note that it was not a one night stand, but happened a few times...

I have known this guy for a while and only recently have we hung out a lot and gotten to know each other better. We have decided to start dating and before we do, he told me he had slept with my friend more than once, who was also his housemate. He said it was just sex to him and he didn't and doesn't have any feelings for her. He told me he wanted to make sure I knew this information before we got involved, as it may be a problem for me.

And yes, now I feel uncomfortable knowing that this has happened, even if it was just sex, it was only about a month ago when they last slept together and it's because it happened more than once. For some reason, it does not seem so bad had it of been a one off.

I am aware it happened before him and I grew closer and decided to date, so really

He hasn't done anything wrong and i've said this.

But he is angry at himself and said he didn't know anything would happen with him and I, or that he would feel this way about me and he wouldn't of slept with her otherwise.

I am unsure how to respond or what to feel, all I know is now I feel uncomfortable with it and find it weird thinking that him and my friend were having sex and now I'm with him.

What is your opinion on this and what would you do, or feel if in the same situation?

View related questions: one night stand

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A male reader, Serpico United States +, writes (13 June 2016):

I wouldnt go near a women who one of my friends already has been with. Zero chance.

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A female reader, Little Heart United States +, writes (11 June 2016):

are you still friends with this person? if so yo shouldn't be. A real friend doesn't do that. and for the guy, well dump his ass he slept with your friend, nice way to gain your trust right? dump his ass

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A female reader, anonymous, writes (9 June 2016):

This is not a problem that will go away any time soon. I would feel like you do. I think I'd walk away from it before it gets to the point you love him but cannot cope with this situ. It's all too close for comfort. Lines are blurred. The start of relationship should be a little more pure.

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A female reader, anonymous, writes (9 June 2016):

It all sounds a bit seedy. Not a good start to a relationship. I dont think this will end well if you date him.

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A female reader, Dionee' South Africa +, writes (9 June 2016):

Dionee' agony auntI can totally see how this would be an uncomfortable situation. You did mention that he told you the truth beforehand so you could make a decision as to whether or not you'd like to proceed with dating . . . why not just let him know that although you appreciate his honesty, you cannot seem to move past the facts. You will not be able to date him and be ok with the fact that he used to sleep with your friend casually. I think that it might be best to move on OP. Good luck

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A reader, anonymous, writes (9 June 2016):

If it makes you uncomfortable, maybe you should end it before you attach your feelings. You'll continuously be conflicted and jealous. Every-time you see her you'll cringe, and you'll never be able to handle them both in the same room.

Don't start dating the guy exclusively if you're always going to be ambivalent about how you feel about him and his past.

He can't undo what's done; and you shouldn't torture yourself with something you're better off avoiding. You'll make the both of you miserable, and he'll end up dumping you!

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A female reader, janniepeg Canada +, writes (9 June 2016):

janniepeg agony auntWhen it comes to casual sex, there will always be people who are not okay with it. For those who try to accept it, it's always okay for other people, but not for people closest to us. Whenever you see your friend you will always be reminded. I think this is uncomfortable for your date too. Unless he's perfect for you in many ways, the fact that he had sex with your friend is something that you always try to get over. It also depends on how your friend feels. It's better if it's sex for her too. If she secretly had a crush on him, that would be a disaster and it would affect your friendship.

I am not even trying to answer from a moral stand point. It's more about getting along with everyone, in your friendship circle without awkwardness. He showed himself to be a respectful person. He told you the truth before you fall in love so deep that by then it would be harder to make a decision. I'd say if you had a doubt it's better not to go forward. You can always date someone else without these issues.

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A female reader, Andie's Thoughts United Kingdom +, writes (9 June 2016):

Andie's Thoughts agony auntI disagree with the anon that you should "grow up" - this isn't a case of jealousy or immaturity; it's uncomfortable for many and suggesting you should "grow up" is invalidating your very valid feelings.

It would bother me because it's not as past as would make it easier to forget. It would also bother me that it was more than once, too.

I'm with Honeypie on not judging people who have casual sex, but also not getting it. To me, whilst I don't think any less of them, I wouldn't want to date them because it doesn't match up with how I feel about it.

An example of my view on it: my boyfriend's roommate-to-be (for at least one year of uni) has had casual sex with a guy friend of hers and is now interested in a non-binary person who is already in a relationship. She's a nice person and says she wouldn't help them cheat, but she's already dangerously close because she's flirting and getting closer, not distancing herself. I don't doubt that it's possible she may let her feelings run away with her (which appears to be happening already) and cross the boundary. I would feel uncomfortable with her willingness to flirt and get close to someone who is already in a relationship, as well as have casual sex with guys, even though she says she's mostly attracted to her own gender and wouldn't go for my guy because he's not one of her male celebrity crushes. Luckily, I'm only a little concerned about her actions, as my boyfriend is completely against cheating, is also uncomfortable with the way she's pushing boundaries and has never been into casual sex - doesn't see the point.

You need to figure out if you can get past this, or if it's best to just chalk it up as bad timing and not date him. Personally, I'd thank him for his honesty, but tell him that it's something I just can't get comfortable with.

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A male reader, Garbo United States +, writes (8 June 2016):

Garbo agony auntIf this was a reverse situation and I was with a girl who did this ... Well, I wouldn't be with that girl. Nor would I care to blame her or him, simply such girl if off limits, sorry, bye.

Idk if there is difference as to how a girl is suppose to feel in this scenario, but frankly, to me, it would be irrelevant. If I was uncomfortable with being with somebody, whatever the reason, then I wouldn't be with that person. So my advice is do what makes you comfortable and if that is a deal reader then break the deal.

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A female reader, Honeypie United States + , writes (8 June 2016):

Honeypie agony auntI would feel a bit uncomfortable too. After all SHE is his room-mate so readily available for a shag that means nothing.

How does SHE feel about him? Did it mean as little to her?

I have always thought people who have sex with their "pool of friends" are not always good partners. And people who can hook up and feel nothing? I know some people are like that, I just don't understand it. Nor do I find it attractive.

I think you have to decide if YOU are OK with it or not, in the long run. If it makes you re-think things, then maybe you just have a bit higher standards than a guy who will sex up his roomie, just to have sex.

Just know, he nor you... can change the past. And you can't change HOW you feel.

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A female reader, anonymous, writes (8 June 2016):

Has he cheated on you?

Were you exclusive when he slept with that girl?

Were you even dating?

If the answers are negative (and they are), I honestly do not see a problem.

We all enter relationships with baggage. Usually men like to feed that illusion that their girlfriends/wives are almost virgins.

But the important thing is that it makes YOU uncomfortable and nothing anybody says will change that. It's a matter of opinion.

My husband knows and has worked closely with two ex bfs of mine. I have worked with one of his ex gfs... It never made us uncomfortable, we'd even joke about it.

If you really care about this guy, grow up and put this behind you. He's honest and regrets his actions, although I don't see why he would regret having consensual sex while both of them were unattached. However it is romantic of him.

Dig deep and understand why this is making you insecure and uncomfortable. Again, my husband has been with so many women. Relationships, longer or shorter, one night stands... It never occurred to me to look back and wonder... I really feel that he hit jackpot when he met me ;)

So work on your self-confidence. He's with you because he wants to be with you.

Obviously he has a choice and you are not his consolation prize!

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A female reader, chigirl Norway +, writes (8 June 2016):

chigirl agony auntIf you feel uncomfortable about it, then why does it matter what we think?

I think most people would feel uncomfortable with this though. This is why there's a bro code and a girl code, and why homie hopping is considered a bad thing. It's generally frowned upon.

Im looking to hook up with a guy right now, and I know for sure one of his friends is interested in me. Reason for not sleeping with the friend: It would most definitely ruin my chances with the guy I actually want. Everyone knows this.

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