Then Jack Happened


Dear Jack,

I’ve been seeing my girlfriend for about six months. Everything was great until we had the talk about our sexual histories. I initiated the talk. The problem is, that her number is way higher than I thought it would be. To the point I’m not sure that I still want to be with her. She could tell I was upset/surprised and then she got mad and we got into a little bit of a fight. It’s been a couple weeks but things are still simmering. I don’t know if I want to stay with her because of the history, but on the flip side, I really like her and things were going well, so how do I get over this, and second, if I do, how do I fix this?

I’ll start with your second question. You need to apologize. That would be the course of action if you ‘decide’ to fix this, and it is the course of action if you ‘decide’ not to, because you should treat her with dignity and respect. The only way that you’ll ever fix the relationship is to be sincere and demonstrate some real understanding of why you’re being inappropriate.

I really don’t understand what the point of trading numbers. You say ‘the talk’ as if it were inevitable. Short of health issues, which should be shared before intimacy, a person’s sexual history is probably pretty immaterial. These questions mostly come from insecurity and its dopey friend jealousy, and nothing will come of it. You get number X, you feel great! You get number Y, and now you don’t. During those six months, when you were having fun and sleeping together and getting on, the number was always Y, and Y has more to do with you than it does with her.

You have to try and account for her perspective and feelings. Look, you just told her that she isn’t worthy of you, morally reprehensible, or gross. Your disapproval is an attack on her worth and an attempt to make her feel bad about herself. What is she supposed to do? Apologize? “Three years ago, I met this guy Bort, he was a lot hotter then you and we hooked up. I’m sorry.” Are you going to start apologizing to her for actions that you took before you even knew she existed? Clearly not. She can’t change her past and, hopefully, she is quite happy with who she is and what she’s experienced. Attempting to diminish that accomplishes nothing and is hurtful.

My tone is a little bit rough, but you need to grow up. You aren’t likely to find someone that fits your perfect formula, and until you realize that there is no ‘perfect,’ your problems will persist.  Remember, everything was great until you discovered she didn’t fit your arbitrary mold. And nothing is different! You’re the same people you were before only now you’re acting spoiled. If you want a successful relationship, you need to learn to accept her for who she is, history and all, or it will never work. I know the defensive response, “Man, I shouldn’t have to date someone I don’t want!” Yes truly. You can dump her. You can never get with a woman that has ever dared to hold the hand of another man.  But let’s be real, she’s not some no-good-nik or murderer, you just disapprove that she was with other people that weren’t you. And that’s not her problem to change.

Listen Delray, there’s a million fine looking women in the world, but most of them don’t bring you lasagna at work. Wait, what? Send your problems to