I'm hung up on my/my GF's sexual past.

"It's the most fulfilling and happiest relationship I've ever been a part of and so, naturally, my brain spends every waking hour tearing it apart at the seams."

🌭Today’s letter writer—our sweetie pie—asked me to edit out some details of their life for anonymity, which is why you will see some things X-ed out and why there are some details replaced in brackets. It doesn’t change any of the letter or the advice!🌭


I’m a XX  year old guy living in XXXXX, and have been with a truly wonderful girlfriend for about XXX now. It's been far and away the most fulfilling and happiest relationship I've ever been a part of and so, naturally, my brain spends every waking hour tearing it apart at the seams. Here's my history and our history and ultimately what I need advice with:

My dating history is something that I've always told myself is not normal compared to my peers and something that, is clear now, I harbor a *lot* of insecurities over that I've never addressed. I can only be described as what may be known as a "late-bloomer". I had friends, honor-roll student, involved in school, but just not good at the whole dating thing. I always assumed once I went to college I'd have a fresh start and lose my virginity, then freshman year went by and nope. Sophomore year I met an amazing girl, it finally happened and we ended up dating for ~2 years, breaking up, then on and off for another ~2 years. There were various reasons why we broke up, but it became clear to me that there was a combination of A) doubt that this person was right for me, and B) a desire to live what I told myself was a "normal" dating life and do things like...sleep with more than 1 person before settling down. So ultimately I was single again....but nothing really changed. I started hooking up with (slightly) more people and sleeping with (slightly) more people but they were still few-and-far between and mostly drunken escapades. When I was in my relationship I was like "oh man I need to break up with her so that I can sleep with more people before ultimately settling down, cause I need to get it out of my system now!" but then I became single and...I didnt care? About any of that? I wasn't exactly ever putting in a lot of effort to find people and hook up with them and live the life I *thought* I wanted to live. But the feeling of being "different" from my peers in terms of dating was very prominent.

I went through the motions for about a year and a half or so, sleeping with a small handful of people a small handful of times, and then another girl came along and we started dating for real. This was the true definition of "going through the motions" as I genuinely had no real feelings for her, I was just supremely bored at the time as I was failing to do what I wanted to do while single so I was like okay whatever back to this, I guess. Another year and a half, another breakup, single again. And finally! For the first time in my life! I genuinely took advantage of being single. I was going on dates, I was hooking up with people, I was experiencing the life I told myself for a few years I wanted to experience. I was even at a point where I genuinely turned *down* hookups from people I had always wanted to hook up with. It was a complete 180, I was sleeping around, looking for nothing in terms of a relationship and then....I met my girlfriend. This stretch didn't last very long, because the first night I met my now-girlfriend I knew how strong my feelings were for her. At the beginning of our relationship, I never thought about my sexual history or being unsatisfied in any way, shape, or form for about the first 6 months or so that we were together. I knew that my dating past was still "weird", at least in my head. I had always been an attractive (yes I cringed typing that - but its true! and its something that caused my anguish because I felt attractive but *still* couldn't hook up with people), smart, funny-enough, personable-enough, [insert accomplishment here that is great and impressive that was edited out for anonymity’s sake], and yet I could count on barely over 2 hands the amount of people I'd slept with in my life. That's weird right? But who cares, I found somebody that I finally for the first time in my life genuinely have very real feelings of love for!

Our relationship has been wondrous. I've never connected with another person like this, and she has so many qualities that I truly cherish. To be honest, one of the reasons *I think* I always kinda just went through the motions when single is because I thought I'd mostly always be single?. I hadn't really ever felt the feelings of "Wow, I can genuinely imagine spending the rest of my life with this person", and I kinda thought I never would, so I figured I had plenty of time to do whatever I wanted, what's the rush? 

As we started to become more familiar with one another, naturally conversations about our dating history came about. I don't open up to people about my sexual past or dating history. The only person I've ever even somewhat spoken to in-depth about it is my college girlfriend. Oddly enough, we've run into many issues in the past where my current girlfriend gets jealous because she genuinely thinks that I used to be some sort of cocksmith running around town knocking boots left and right. It would almost be funny if it wasn't so dark that the reality is the only reason she thinks that is because I haven't been truthful. When we talk about her past, though, my mind just...crumbles. She's more experienced than me, by what I perceive to be a decent margin, but also our histories are just...different, which is okay! All of this is okay. And that's a statement that I find myself saying 20-30-40 times a day...that this is okay and this is normal and her past is A) not my business, B) not a problem unless I'm selfish, and C) has no affect on our relationship. But the retroactive jealousy has been *crushing me*, day-in and day-out, for months now. To the point that I think about her past with other guys....while *we* are having sex. And I'm not even insecure about our own sex life! We have amazing sex! We are very open and communicative, we are good about sharing our feelign and emotions re: sex, and she's been open about how there are many parts of our sex life that are brand new to her (that aren't new to me, yet here I am getting jealous).

I don't know what to do about it. Where I've settled is this: 1) her sexual history is what a *normal XX year old's* sexual history should look like. I am the one who has a different past, and because MY past is different I am not free to hold it against her for being normal, 2) I know, to my core, that I trust her and do not think that anything in her past affects our future, and ultimately.....3) I think that my jealousy isn't about her, it's about my longstanding desire to experience a life I never did, and having frustrations that I think I'm in a relationship that I want to be my last but I now don't know if I'm truly ready and I feel so insanely fucking...STUPID for having this be a reason I'm not ready for her. But maybe this is just how I am? Maybe I just WON'T be ready until I solve for this annoying jealousy?

I'm worried that I'm going to lose her over this, because I don't know how to solution for the very toxic way I think each and every day. I honestly feel like I need to just, like, take a month and sleep around and get things out of my system, but I know that's not realistic at all. But I also cannot live with this jealousy forever, because the way that it makes me feel is so shameful, guilty, disgusting, pedantic. It's so confusing to acknowledge that being jealous over this is inherently wrong and unfair yet being unable to get myself to feel differently. And it's...really uncomfortable to think that I may have found a person I can imagine spending my life with but I'm now considering losing her over something so inconsequential?


OH BOY OH BOY!!!! There is some really good news here for you: this is so incredibly normal. There’s no way for this to not sound condescending so I pre-apologize because I don’t mean it that way, but I feel a wee little bit bad for you because you’re so normal and you think what’s happening/what you’re feeling/your history is so abnormal. It’s the letter writing equivalent of calling your doctor because you sometimes have leg cramps after you work out. Like yes, they hurt, but they’re very normal/common.

NOW!!!! That doesn’t take away from the psychic pain of your dilemma (ps I mean psychic as in “relating to the soul / mind” not as in “can see the future”). Knowing that other people are also freaking about about some of this stuff does not make you all of a sudden go, “Oh, chill. I’m not upset anymore.” I just want to remind you that you’re not wildly off base or completely adrift with absolutely no hope of turning this around. To quote Paul Simon, “The cross is in the ballpark.” This is surmountable and addressable.


As I see it, you have a few nebulous, interconnected problems. Think 14 iPhone headphones tangled up together but also tangled by themselves. Nightmare! Here’s what I think are the problems:

  1. You’re worried about your own sexual past.

  2. You’re lying about your own sexual past because of #1.

  3. You’re worried about your girlfriend’s sexual past because of #1.

  4. You’re ruining fun times for yourself and your partner because of #s 1-3.

  5. Because of #s 1-4, you’re considering going out and sleeping with other people.

I’m sure there are other little issues here and there, but I think those are the big boys that we need to worry about. I’m going to go backward from number five to number one and address them each.

You’re considering going out and sleeping with other people.

For the love of all things holy, please do not do this. I will pay you $7 to not do this. Not only would having a fuck-around-suck-around month be INCREDIBLY, UNBEARABLY hurtful to your lovely girlfriend, but it also won’t actually do anything. Anything at all. It’s the equivalent of drinking 3 bottles of wine because you have appendicitis. Like, yes, technically, drinking 3 bottles of wine might make you feel a little bit better about the problem because it will numb you, but it most certainly will not help with your appendicitis. In fact, it will make things worse!!! And you will ultimately feel worse because you will have both an inflamed appendix AND a hangover.

I know you know this is a foolish solution to the problem at hand, but I just want to let you know that no matter how many randos you sleep with— even if you have a really fun time— you will not fix the issue which is internal and actually has nothing to do with # of sexual partners. If I thought that you going and sleeping with a bunch of people would magically fix this, I would absolutely encourage you to break up with your partner and go bang your way through your city for precisely 7 months and then try dating again when you’re more ready. I’m not going to pretend that having casual sex is hallow or empty or whatever else that people ascribe to the act; it can be very fun!!! But it cannot make you happy or fulfilled. So let’s drop this idea. No offense, but this plan sucks.

The highest likelihood outcome of going around sleeping with people for a month is that you hate yourself for leaving a good relationship and you feel even worse. Please do not pick this path.

You’re ruining fun times with your partner because of your insecurities.

I can’t simply tell you stop thinking about the things you obsess over and then you stop, and unfortunately, neither can you. (At least I assume so, otherwise I would hope you would have simply done that). But what I can tell you is that intrusive, unhelpful and unhealthy thoughts are super common. They seem to be especially common for people in new relationships around the idea of jealousy or unrealistic expectations from their partner. Part of that, I imagine, is that when you’re in a new relationship or experiencing jealousy, you’re uncertain and insecure. You don’t know what to do. So your brain— who is a big brat sometimes!!!!— says, “I have an idea of how to deal with this problem. And you’re not going to like it but…hear me out… what if we just think really unhealthy bad things all the time?????”

Obviously, this brain tactic sucks shit to deal with. The best thing you can do (at least in my experience) is try to stop and label those thoughts. You literally stop yourself and say, “This is an unhealthy thought based on being insecure right now. Thank you for stopping by thought, but I am not going to invite you in.” Will this work 100% of the time? No. But labeling unhealthy, obtrusive or obsessive thoughts as such goes a long way to taking their power away. It’s a little bit like after you’ve watched a horror film and all of a sudden your brain becomes convinced that there are people outside your window or under your bed or behind the shower curtain. It becomes convinced of that because you’ve just spend 2 hours telling your brain that there is a threat. You can’t make your brain not be scared, but you can remind your brain/body/self that, “There is not someone actually under the bed, I’m just amped up because I just watched The Conjuring.” Again, admitting that the fear is unfounded doesn’t chill your brain or heart rate out immediately, but it’s a necessary step to cooling off.

Treat your jealous thoughts the same way. “This is an unreasonable fear but I’m feeling worried/insecure/jealous right now because X happened. This isn’t the truth, but the story I’m telling myself right now is that Y is going to happen next.”

Ultimately, you’re going to have to work on your insecurities (we’ll get to some of this below) which will go a long way to helping with this, but it’s not like you’re never going to feel worried/insecure/jealous again, so you need to learn how to cope with how your brain works.

You’re worried about your girlfriend’s past.

I get it. I get this 100%, but I also think that you are correct in thinking that your concern has nothing to do with your girlfriend and everything to do with your past.

I would strongly recommend you coming up with some kind of comforting line / mantra (sorry, I know it’s corny as all hell!) that you tell yourself when you start thinking about her past. It might be, “This is none of my business.” It might be, “She’s with me and she wants to be with me.” Whatever helps even 1% to get you away from thinking about this is good. Start there. Get a mantra and repeat it to yourself over and over. Then go do something else! Go for a walk. Take a hot shower. Read a book. Play Smash Brothers. I don’t know or care, but go do a different thing than what you’re doing if you can. Your brain is literally getting stuck and you have to get it focused on something else. Even tossing and catching a ball with yourself helps because your brain has to focus on that and not some weird shit you made up about your girlfriend.

Your girlfriend, when you open up about this— AND I DO MEAN WHEN BECAUSE YOU’RE GOING TO TALK TO HER—can absolutely play a supporting role in helping you deal with these issues, but it cannot be about her past at all. Do not bring that into play!!!! I will cover what I think you should say to her below, but for now please know that you should not address her actual sexual past with her. That’s her business. It has the same bearing on your relationship as what her favorite outfit was in 7th grade, which is to say: NONE. No bearing. She could have been having sex every day with Brad Pitt circa Once Upon a Time… In Hollywood and it still wouldn’t have anything to do with you two because she wants to be with you. Do you know how I know this?


She is not comparing past partners— you are. I’m sure she does not think of them in anything other than a fleeting, “Oh yeah, that guy used to put ketchup on his burritos that was so fucking weird,” kind of way. The way we all think of our exes/ex-hookups. I guaran-damn-tee you she is not sitting around thinking about how experienced her exes were.

You’re lying about your past.

OK!!!! NO!!!!

You have to sit down and have a conversation with your girlfriend STAT. Here is what it would sound like coming from me (please obviously change this so that it’s coming from you. Fill in your truths!!!!): “Perfect angel, I’ve not been doing so great recently and you may have noticed this* and I wanted to talk to you about it. Most of it stems from my insecurity about my past and I haven’t been totally honest because I’m so insecure. I inflated how many people I’ve been with because I’m so concerned that I’m not experienced enough. I was a bit of a late bloomer and that fear of not being adequate sexually really stuck with me so no matter how many people I’ve been with, it always felt like I was behind somehow. I know that this has nothing to do with you, but I’ve been letting it seep into our relationship and I’m sorry for that. I’m going to really try to work on it. I might need extra reassurance sometimes from you that I’m what you want because I’m really getting in my head thinking I’m not enough. And I know it’s not true, but that’s the idea that gets stuck. I love you and I don’t want to mess this relationship up with my jealousy or insecurity. I’m sorry I inflated the stories.”


Now, your girlfriend is 100% going to be totally cool about it and loving and she’ll probably give you a big hug because she’s a nice person and she gets what’s going on. In no way will this be a big deal for her, I virtually guarantee it. She would MUCH RATHER you open up and tell her the truth than be doing this unhelpful suppression shit.

Also, good news bears—your girlfriend doesn’t give A SHIIIIIT how many people you’ve slept with. I’ve been friends with thousands of women at this point and many of them have been into men and never once—EVER—has any of them been like, “I’m concerned Steve hasn’t fucked enough people.” Certainly, I’ve heard from them, “Steve is concerned that he hasn’t fucked enough people and it’s making him uncertain of commitment and I’m freaking out about that.” But never ever ever ever has a female friend of mine been like, “I wish he’d had more casual sex because I think that would help make our relationship better.” Everyone—everyone!— would much rather have a partner who listens to what they want in bed than someone who happened to have a specific number of past partners.

Stop lying; it’s required.

You’re worried about your own sexual past.

PAL! I have some excellent news for you: no one but you cares, but not only that— you probably have a way more…active…past than you’re even imagining. If you’re really interested (not that I think comparison is healthy for you) you can check out the Slate calculator where they let you compare your sexual history to others. (Well, others who have been on Slate).

I’m almost certain that you’ll find that your “number” is quite high compared to most people (NOT THAT THAT MATTERS). Why am I certain of this? Because everyone—all of us— have been tricked into what I internally refer to as How I Met Your Mother Syndrome. Shows like HIMYM (which I actually haven’t seen, sorry) taught us all that everyone is Ted Mosby, constantly hooking up with new people, dating new people, and then having messy but short break ups only to find a new person they’re into right away. You know why? BECAUSE THAT MAKES FOR GOOD TV.

Literally the rules of writing are that your character has to want something. That’s like the main rule of writing. And giving your main character a new “want” every episode for 208 episodes is HARD so they took an easy way out and made Ted Mosby want a new woman who he couldn’t have. And then he could have. But then he lost. And then he wanted again.

That does not mean that normal ass people are doing this!!! Most people don't have as many exes as Taylor Swift or as many hookup partners as Wilt Chamberlain. Those are celebrities with abnormal ass lives and lots of money and assistants. That is not the life of ANYONE you know. I swear. I know I’m right about this. Most people have had a few partners. A lot fewer than you think.

The reason you feel insecure is because 1) HIMYM Syndrome that taught you that everyone was having a lot of sex/experience constantly. 2) You were a late bloomer.

Almost every late bloomer I know (myself included) feels this inescapable sadness about having missed out on what everyone else got to do in high school. I’m not going to pretend to you like, “Oh you would have hated high school sex. It wasn’t even good!!!!” I think that’s bullshit. You lost out on something and you can be sad about that! That’s reasonable! Sometimes I get sad that I’ve never hooked up in a car even though objectively I know that hooking up in a car probably SUCKS. But to me, it’s about the fumbling high school mess of not having anywhere to go and needing to be a horny teenager with someone, and I never got that experience.

You’re allowed to be sad that you missed out but you have to stop letting that sadness and grief guide your current life! You’re about to miss out all over again because you can’t let go. You need to find a HEALTHY way to cope with your “lost” youth years, because that is the crux of this issue.

You think your sadness is unreasonable and it’s not. The way you’re coping with it is what’s unreasonable and frankly, unhelpful.


I’m sure I didn’t magically solve all your problems or anything. I can’t do the work. Unfortunately, you have to do the work. I have some work to do on these exact issues myself. It’s not going to be magical. It’s going to be life-long. You’re not going to go to therapy four times, learn how to change your thinking and then never have insecurity about being a late bloomer ever again. You’re going to struggle with it your whole life. But if you actually start addressing it, it will become a whole hell of a lot easier.

I do think you should try therapy if you can afford to. Will it be uncomfortable at first? YES IT WILL, SWEETIE!!!! But I also think that your relationship is worth a couple hours of discomfort. Eventually, you’ll get to the point where therapy is no longer excruciating. You’ll get used to talking to someone about your fears and concerns. I promise you that TONS of people come in about this exact issue. Almost every self-dubbed “late bloomer” has had similar issues. Your therapist will have 100% dealt with this before.

One last thing: please slow your mental roll a little bit in regards to your girlfriend. You do not have to commit right now to marrying this person, even if you love them love them love them. Give yourself some space to breathe, to enjoy one another. Commitment is probably going to always freak you out a little bit because of the whole late bloomer / I feel like I missed out thing, so don’t rush. Talk to your partner about your concerns. Be open and honest. I’m not saying that you should say, “I’m thinking a lot about fucking other people because I don’t want to miss out!!!!” But you can say things like, “I’m kind of freaking out about us moving in together because of my fears about commitment. I’m not suggesting I don’t want to commit, but just that it’s a bit of a trigger for me, so if you feel me pulling away, I’m sorry. I’m going to work on it, but also feel free to call me out. I’m trying my best.”

Ultimately, you’ve got a great partner who is totally going to be there for you and understand. You’ve got a common problem that (especially with the help of therapy) you can address and work on.

You don’t need to fuck everyone to know your girlfriend is great. It won’t make you any happier. I promise you.


❤️❤️❤️NOTE: because so many sweetie pies have been asking questions, it can take up to a month or two to answer them. I’M SORRY. I try to answer “urgent” / timely letters ASAP and more general questions later. 


Sophia Benoit writes this very newsletter; she also writes about sex & relationships for GQ, tweets about everything else at @1followernodad, is a researcher for Lights Out With David Spade, and has had bylines in The Guardian, Reductress, Refinery29, Allure, and The Cut. You can reach her or yell at her at 1followernodad@substack.com.