Dear Em & Lo: My Boyfriend Can’t Handle My Sexual Past

photo via flickr

Dear Em & Lo,

I have been in a relationship with my boyfriend for almost a year now. We have known one another three total years. In the beginning of our friendship, I treated him like a best friend, and told him quite a bit about my sexual past with ex-boyfriends. It severely affected him and bruised his ego. I never had a clue that I hurt him so badly until he told me his feelings.

We have since started to (try) and repair the damage that I did, and I have made it a point to try and nullify it. But he is still severely affected by what happened and to be honest, after quite a few months, I am wondering when he will come around. I have made a point to boost his ego. Tell him he is the best in bed, that he is very attractive, etc. He still finds himself in whirlwinds of depression and he thinks back on that time period of when he was in the friend zone. What can I do to pull him out… or can I at all?

— Dating the Green-Eyed Monster

Dear D.T.G.E.M.,

This is the best and worst thing about falling in love with your best friend: you’ve already told each other everything and you already know everything about each other.

We don’t think you’ll ever be able to make your boyfriend forget the things you told him, so the only thing you can do is to help him put those things in context. We’re guessing that you’re not the first person he’s ever dated. Surely he has kissed other girls, had crushes on other girls, slept with other girls, fantasized about other girls, been dumped by other girls? Maybe he’s even been in love with other girls. And clearly those memories in his past don’t affect the way he thinks about you. So you need to remind him of this.

Tell him to try this: Every time he is assaulted by some vivid image of you with another guy, he needs to force himself to call up an equally vivid image of him with another girl in his past. A friend of ours refers to this as the “nuclear option” for dealing with jealousy. He’ll be forced to realize how little each of these girls now means to him in the context of his current relationship. Tell him to do this every single time he thinks of one of your exes. Eventually he might start to realize that our past can be no big deal if we stop poking around at it.

Beyond this — and everything else you’ve told us you’re already doing — you can’t do much more. The problem is really his to get over. You can be supportive and complimentary and offer rave reviews of his, er, performances. You can hold his hand and tell him he’s wonderful. And if he still can’t get over your past, then he may just have to become part of your past.

And everyone else: let this be a lesson to you. We know it’s tempting in those early, boozy, flirty stages of a relationship to share everything about your sexual past. Every single nitty gritty gory orgasmic detail. We know it’s tempting to tell your partner, “No, go on, tell me, I really want to know who was the best sex you ever had.” But you should know that long after you’ve dished the dirt, your partner will still remember these things. Men: years after you’ve forgotten you even slept with that bartender, your girlfriend will still remember where she worked and what it was she did with her hands that drove you wild. And lades: decades after you’ve forgotten you ever slept with a guy who played hockey, your guy will remember exactly what you said about the size of his penis. If you think you can handle this, then, by all means, blab away. But don’t come crying to us and say we never warned you.

So there,

Em & Lo



  1. I can’t think of one relationship question where everyone in the comments won’t say to dump him/her. Either they are they the ones that are controlling manipulative in the relationship/single/ or has multiple partners. Each relationship will have problems and insecurities either you deal with the BS or you don’t. All relationships have BS its just how much your gonna put up with, these days it’s a lot.

  2. Hmmm I think if u brokeup or gone far or get married.U left him suddenly and he become sad n alone.As he is addicted to you as close friend and take care of you a lot ,still he do.only way is too call him after few days,tell him you are happy or not ,ask him about his life, you was so special for him before but now u need to be a normal person in his subconsious,He worry about you.It may take a year but once he started feeling happy and again get confidence over him self ,He will try to hangout with some else and gradually you get fade out.May be he is standing there because he know you take him as inner strength of yours.So he’s just carry as usual.he don’t need any drama,just waiting for time when he feel his job is finished now and you will be not broken if he vanished.Also it depends what u mean to him and which relation he impose more on you.Love,sex,friendship,Hasband rights.

  3. I have been through this. Just saw these posts. From personal experience—this behaviour is the tip of the iceberg. He won’t ever be “normal”. If your past “hurt” him, then he is probably a narcissistic a man who wants to control and dominate you. And since he can’t “control” your past behavior he can’t have the control he wants and is unhappy. He doesn’t want love or sex—he wants control, or power, power over you. A more normal guy, might be a bit insecure or jealous (not the same as “hurt”). But having a relationship with you and your love and affection would be more important than what happened in the past. I agree it’s best not to give anyone too many details about your past, but if a guy is like this, even if you don’t tell him about your past, even if you don’t give him details—he will still “suspect” things. You can’t win with controlling and narcissistic men and they can’t be helped. Best to get away from them as fast as possible.

  4. When you were friends your past was not a problem; but now that friends have become intimate partners it is. A friend does not do that to a friend. You can’t change anyone’s mind or emotional state only they can and if wallowing in poor little me matters more than a friend then this can’t be fixed.

  5. ^ you’re both right, Frannie. It is manipulative, emotionally abusive slut-shaming, AND it is a manifestation of hurt feelings and insecurity.

    My first girlfriend had way more sexual experience than me, and it drove me freakin’ nuts. There were a few things at play:

    1. She made me “wait”. To a guy, that makes absolutely no sense. It was like, “let me get this straight: our relationship is SO special that WE can’t have sex yet, whereas if I mattered less to you – and you mattered less to me – we’d be fucking right now? Like the last guy, who didn’t give a shit about you, yet boned your brains out? oooookaaaaay….”.

    I could clearly see what this truly meant: she was less tempted by me sexually than she was by previous guys, no matter what crap she spouted about preserving the specialness of our relationship by not sleeping with me. That was MADDENING.

    2. It blew apart the boundaries of my fragile, developing “man-box” (term given to the self-imposed, intra-gender, and inter-gender expectations of “real men”). If I was a “real man,” in other words, I’d be the one with more sexual experience. Not only that, but since the her previous guys had more sexual experience than I did, I felt like I was being blown out of the water.

    3. She did like to rub it in in subtle, plausibly deniable ways. “Gaslighting,” if you will (meaning, provoking and antagonizing your partner, then telling them that they’re nuts for feeling provoked and antagonized. I’ve learned so many terms from Em & Lo!).

    So I reacted much like the pathetic little crybaby in the original letter. A combination on immaturity, inexperience, and, yes, manipulation on the part of my girlfriend (not that that’s what’s happening here, just sayin’) made me act crazy and not nice.

    That was almost 15 years ago. Since then I’ve matured; I’ve racked up my own high number (so there!); I’ve CONSCIOUSLY attacked my own insecurities using introspection and logic (most people of both genders will never do this – always easier to externalize and blame, so don’t hold your breath); I’ve realized that I PREFER sexually experienced women; and I’ve solidified the boundaries of my man-box – they’re way harder to knock down these days.

    Point is, some people change. The guy might not be an evil misogynist. He might just be an immature dipshit. Of course it, might take him YEARS to come around, so yeah – in the meantime, dump him. He needs to work this out on his own.

  6. the response was too kind. dump him. he sounds creepy at best and emotionally abusive at worst. you’re being slut-shamed. you need to be with a real man who respects you, not one who is threatened by your past (your PAST!), because this is just the tip of the iceberg. i agree with hannah. this isn’t ‘insecurity’, it’s possessive and manipulative.

  7. I am someone who can’t really handle knowing the romantic past lives of people I fancy, mostly because my own is sparse. So, I know not to ask any questions about exes. I have some friends who have told me things about their former partners and I know that I could never date them now.

    The thing is, I know this is my issue. I would never punish or blame or berate someone for their past just because I’m jealous or insecure. I realize that this is a situation that I need to walk away from because it’s not good for me or the other person. I think Letter Writer, you need to do the same. Walk away because no one should make you feel less than.

  8. Tell your current BF to stop acting like a whiney toddler. He knew all this before he started dating you. Your past is what makes you, you. Don’t apologize or feel guilty. I think the real issue is he doesn’t think he’s good enough and is trying to drag you down by always making you feel guilty. This is chronic behavior, if it keeps up dump him. Find someone who like every part of you and is confident, because there’s nothing sexier than confidence.

  9. I don’t agree with the final paragraph. I was in a relationship like the original posters, where the guy knew a lot about my sexual past out of virtue of our long friendship. It sucked,and he used it against me constantly. I’ll just say that my “number” is in the single digits, and I always wrap it up and play it safe… but he still made me feel like a whore! I think this can be a huge red flag, and the problem was completely with him and not with me for just being honest. This same guy eventually started even more possessive behavior. He didn’t want me meeting with my male friends or even male colleagues!!!I and i could never mention any ex ever, even when it was relevant to understanding huge aspects of my self. I think that level of possessiveness is, frankly, scary, and a guy who is displaying insecurity about your sexual past might very well want to extend his ownership of you to other aspects of your life as well. This behavior tends to escalate, if nothing else.

    Current fiancée, on the other hand, talks in depth with me about both of our sexual pasts. He cares a lot about my feelings and my sexual pleasure, and he is always eager to know what has worked and not worked with other people. Yeah, I get jealous hearing about him with other people, but I don’t want to date some virgin who doesn’t know how to give head either, now do I? I believe in full honesty, since any knowledge about your partner’s past can improve your skill as a lover for them. If you can’t suck it up for such a huge, desirable benefit, then you’re being insecure and selfish. I say dump the loser, and get yourself a real man!

  10. “Severly affected” and “depressed” about your past?! How old is this guy? Because unless he was an inexperienced virgin before you started dating, I feel that this behavior is really over the top. What a whiner!

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