My Girlfriends past is preventing me falling in love with her

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    Hello all,

    I am a young man in my early twenties who has never considered themselves particularly good at dating, in part, because I struggle with generalised anxiety. When girls would express interest in me, I would talk myself down from doing anything about it, paralyse myself with possibilities, until the only thing that made sense was inaction. For years I remained single, until one day I decided I’d had enough, and I decided to conquer my self sabotage. I wrote extensively, began dating online, and for a time, it seemed I had finally made it.

    Unfortunately, this was not the case. I am plagued by a terrible obssesiveness that was present in my previous relationship, other crushes I’ve had, and I’m forced to consider the possibility that this may have played a role in my dislike of dating altogether. You see, I fixate on my partners previous sexual partners. Relationships don’t seem to bother me so much as casual hookups. My new girlfriend is wonderful – kind, understanding, sensitive. For a long time, she dated hoping to find a relationship, but were strung along by boys (and girls, she’s bi) who were only looking for something “casual”. None of these bother me particularly. Even the “friends with benefits” situation she had for awhile – because I can understand that in itself is a form of a relationship, and it ended because she caught feelings. What I cannot move past is learning that my new partner once hooked up with one of her friends and their boyfriend – who are polyamorous – on a couple of occassions.

    I must have approached this from every possible angle, and the conclusion is usually the same – if an attractive couple told me they wanted to sleep with me, I was single, drunk, and nowhere near as insecure, I almost definitely would have accepted. I can understand that, my girlfriend, having never had a boyfriend before, values me far more than a couple of one night stands with her friend and their boyfriend. Yesterday they told me they were close to falling in love with me, that before, they had believed they were in love, but it was only infatuation. I understand it was 2 years ago – and while my life has been uneventful in that time, a lot has probably happened for her – she is at College, afterall. She’s told me she has no desire to sleep with this friend again, and presumably, she has had plenty of opportunities in the past. Her reason for this no longer happening was “not seeing them enough and deciding she wanted a relationship” – though I obsessive over this first one, that it could have happened more if only they’d “seen them more”, the second one is really of more importance – they decided they wanted a relationship. This couple sleep with other friends of theirs too – this in not hugely uncommon among gay communities in London.

    It saddens me greatly, because this discomfort and obsession I seem to have strikes me as deeply regressive. I admit I am insecure about sex and sexuality, but there is nothing inherently wrong with what happened. It was also two years before they even knew I existed. I haven’t spoken to my girlfriend too much about it – she knows I feel a little insecure when it comes to her past, but I tell her it is my problem (it is) and that I will deal with it. The sad thing is, I struggle not to think about it. Yesterday for instance, I saw this friend of hers in an instagram post from a mutual friend, and immediately I am set off again, feeling bad, not being present with my partner. She can sense something is wrong – but I don’t want her to feel bad about it, and I don’t want her to think lesser of me either. I question whether clarity will make things better or worse. Today I have considered that I could ask them if it ever meant anything to them – perhaps if I still feel like asking her this time next week.

    In terms of actual damage done, there is little. None of the conversations where I learned of this event were heated, I simply became a bit anxious and withdrawn. I’ve made it very clear that they never did anything wrong – they may even not know that it still bothers me. They are a very apologetic person, I have no doubt they would apologise for doing it, even – but they shouldn’t have to. They have done nothing wrong – this is something I need to try and accept and move on from, but I do not know how. We are both very happy together – but as I’ve said in the title of this post, I am afraid this obsession is holding me back from truly falling for my girlfriend. I feel wounded, and greatly ashamed. Any advice would be greatly appreciated.


    Hi Shaydee

    I think you have a really good perspective on this already. You have a lot of emotional maturity and self-awareness.

    Please only answer the following if you are comfortable.

    How do you feel about your own sex life with your partner?

    I only ask because on the surface a three way sounds like a fun thing. I would think of a partner as sexually adventurous if they were open to things like a three-way. But I hear that three ways don’t always go well. If anything, it tells me that your girlfriend is open minded.

    I’m curious about your thoughts and feelings about this? Does it raise any fears for you? I would imagine it could feel intimidating for someone who has a different background and has experienced anxiety and difficulties with relationships previously.

    It’s okay to have different experiences and backgrounds. You are different people! One positive thing that you can expect in the future is that you have an open minded partner. I’m sure that together you can have much better experiences than a three way situation. That is only something that she only wanted to try a couple of times. She will want to be with you more than a couple of times for sure. Clearly, a loving relationship is much more fulfilling to her than a three way.


    <p style=”text-align: left;”>Hi Shadee,</p>
    I can see your emotional maturity shine through. Asking for help is a true sign of a desire to grow. I’ve always found the way forward in a tricky relationship situation is through talking. Why not share all of this with your girlfriend? In fact just send her the letter just as you posted it here. It’s clear you want to be able to move forward and let this go but are struggling on how. Maybe by talking to her you can begin to see a new perspective and hear her response to your letter. She is lucky to have someone so caring and willing to be vulnerable and wanting to grow.

    There is a Buddhist story of 2 monks who came upon a woman crying because she could not cross a river so one monk picked her up and carried her across. He set her down and the 2 monks continued on their journey until the other monk stopped and said ‘I just don’t understand, how could you have done that, we are not supposed to touch women.’ The first monk turned to him and said ‘I put her down on the other side of the river but you are still carrying her.’

    Sometimes we move forward when we can put the baggage down and let go. I hope this helps.


    Hi Helcat,

    My own sex life with my partner is going pretty much as well as it could, though she is currently stressed with her College work, and I am secretly stressed with this. I am open to exploring pretty much everything she’s interested in doing, and she’s told me I am probably the best she’s been with, though this was admittedly after confiding in her about my own insecurity around sex.

    She has also asked me if I personally would be open to a three way, which I would be. She’s expressed that she’d only want to do it once or twice, and probably not for a few months at least.

    It does raise certain fears for me yes, for one, I wonder whether I would not be good enough compared to the other person, or perhaps, come the actual event, I wouldn’t be as into it as I thought. It’s certainly intimidating for someone who has only been with two people individually before.

    You are correct that a loving relationship is clearly more important to her than a three way. As strange as it sounds, I cannot seem to get past the notion that this three way may have been some kind of formative experience – something that her and this couple will share that will always be special to them. Maybe, in an individual sense, more special than any one time we have slept together. Even if we did have a three way with someone else, for instance, it would not be as special as the first time she did it.

    I can respect this is certainly something I will have to get past in the future. Say this relationship shouldn’t work out for any reason, and I’m dating again, it’s likely I’ll end up meeting someone who actually did have a fulfilling relationship before me, maybe even one they would have liked to stay in. My current partner, it seems, never did. In my mind, this event is the closest thing, though I’m sure in reality there were more meaningful sexual experiences in her past. For me, the reason for my obsession is that she’s still friends with this couple. The events that brought together my first relationship were a lot more idylic and romantic than this one – but I don’t look back too fondly because of the terrible way that relationship ended. Had things ended on amicable terms, and were will still friends today – as my partner is with this couple – I’m sure it would be a lot different.

    I understand that obsessive thought is often rooted in some kind of fear, but I’m not really able to work out what it would be in this case. Do I sincerely think my partner would leave me? Absolutely not. Do I think this three way was more important than our relationship? Not a chance. Back then, the idea of looking for a relationship alone was more important than this event. So what am I afraid of?

    Thank you for your kind words about my emotional maturity, it is much appreciated.



    Hi Jalene,

    Thank you for your response. I would normally speak with my girlfriend about any issues I have with our relationship. The reason I am granting an exception here is because I’ve researched people who face a similar situation to my own and what I’ve learned, is that in almost every case, talking with a partner about these feelings causes more issues. It can feed the obsession by giving you more details of the event, and it tells your partner you are insecure, which is generally an unattractive trait. I don’t want to scare them off 🙁

    She’s also presently doing her finals for College, so I don’t want to give her any more reason to be stressed. It’s deeply upsetting that I can’t speak to the one person I would like to speak to this about.

    I also wonder about the nature of obsession – say I did ask her how important this experience was – would it put things to rest, or would I find something else about the event to obsess over? The nature of my obsession has definitely changed since I first experienced it. At first, I was worried about my own performance – that I couldn’t “deliver” the kind of pleasure that this experience did. Now, this detail doesn’t particularly bother me. Then, it was the notion that she would have done it again, which I have now put to rest. I would like to say that this question of how important it was would be the very last obsession, but to be honest, I could not tell you.

    I’m presently trying to get used to the idea of uncertainty. Yesterday, I stumbled upon a helpful means of thinking about this, though I have been struggling to stick to it. Proposing this was an incredibly important event, formative in my partners sexual development, something which brought her and this couple she’s friend with closer together – consider the present. Now, they don’t see each other for it to not be a little awkward for her (she’s awkward around every friend she doesn’t see that often). The conclusion of this experience was that she decided she wanted a relationship – or it reaffirmed she wanted a relationship – and this would lead to her finding me. It’s true that she wanted one beforehand, but this didn’t change her course in any way – or perhaps, having slept with a couple, she was shown the connection she was looking for. If this wasn’t an important event, the outcome is still the same. Regardless of these details I’m obsessing over, the present is what it is, and here, this event seems to have no percievable bearing on anything.

    Thank you for sharing this Buddhist story, it’s certainly very relevant here. In a cruder sense, I have heard another sufferer of this kind of jealousy express the following: “by obsessing over your girlfriends previous partners, you invite them into the bedroom with you”. I have hoped that through thinking I might be able to give myself peace, but it’s possible that letting go is the only option.



    Hi Harry

    It’s definitely interesting hearing your opinions and concerns about three ways.

    I would perhaps agree, if they’d repeatedly shared this experience. Say if it were more of a poly relationship between the three of them.
    But it sounds like they tried it a couple of times and decided it was better to remain as friends. So perhaps not so much a relationship style bond, still just a friendship bond. Perhaps the experience actually meant more to the couple because they got to explore together?

    From my perspective, I think it would be better to have a partner when pursuing a three way as long as everyone was comfortable. It would seem more awkward being the 3rd wheel if you will. But I’ve never had a three way. So I’m really just guessing. Your gf might be able to share her opinions about this.

    Also, I think that sleeping with a partner is romantic than a three way. A three way seems more like a fetish or something to do for special occasions or to add spice every now and then. Considering that your partner said she would be open to it once or twice. Likely she agrees.

    Perhaps you’re thinking about it because you’re considering trying it as part of your relationship? It is a big decision and it is hard to say how it would affect the dynamics of your relationship. As you said, it is a bit of pressure if you both decide to go down that road. If you’re not sure about pursuing an experience like that it might be worth revisiting that discussion. Or at the very least discussing your concerns about the situation may ease your fears regarding it.

    Please feel free to share any thoughts!

    It’s good to hear that things are going well in the bedroom in your relationship. She’s a lucky lady to find someone like you after having difficulties with her previous relationships. I hope that she is treating you well too.

    Wishing you both all the best! 🙏


    Hi – thank you for explaining.  I agree that college finals are not a good time to add more stress.  This summer, when you are both less stressed would be a lovely time to share.  I disagree that sharing our vulnerabilities and fears makes us appear insecure.  In working with my therapist and my partner of 15 years (who also goes to a therapist on his own and we go together), I’ve found that communicating what I need as well as what my fears are with my partner when done in a healthy productive way allows us to grow closer.  My therapist helps me craft what I’ll say so it is transparent, not needy, and lets my partner know how they can help me move forward.  Recently I felt insecure about something he had posted on his blog and I shared that I was feeling excluded from his blog and that I would love to be included in some way.  It was SCARY as hell to tell him this but we have both agreed that we want more intimacy and connection in our relationship.  I reminded him that I was coming from this place to share my needs.  I was so afraid he would see me as insecure but instead, he appreciated hearing what I was feeling and did include me in his next post – he was caring and lovely which only made me love him MORE.

    I wish you well in your relationship and hope that you can feel the feels, honor what you are experiencing and then let go to move forward 🙂

    Cheers, Jalene


    Hello both of you, I hope this message will reach you both. In the end, I did decide to speak to my girlfriend about the situation. It brought us closer together I felt, and we had a very nice day together.

    To put it frankly, it sounds as though my girlfriend was at a different point in her life, in which she was somewhat depressed and trying to “feel something” by having casual sex. She told me she felt empty afterwards, and this particular liason – the threesome thing – was not great. This is enough to ease my feelings for now, though I must admit, one person whom I know she did it with is kind of triggering to me. I just do my best to remind myself it was not important, and given it was two years ago, it is well in the past. This still involves me accepting somewhat that my girlfriend has had better sex with someone else, but I doubt she has had a better partner, from what I’ve heard, so this seems somewhat unimportant by comparison. Even so, how good can an experience be if it leaves you feeling empty afterward?

    Unfortunately, the following weekend me and my girlfriend met up again and when she got a little too drunk, she started crying and said how she still felt I was angry at her… I wasn’t – in fact – I explained calmly, I never was angry at her, but myself. This seems to have put things to bed once more, but if I can be honest? I’m left with a feeling of dread. It felt as though as much as I tried to reassure her, she was still convinced somewhere deep down that I was angry at her, even though I never, ever said that. It sounds like she is dealing with her own mental baggage… I hope with time she will be able to move past it. Her finals are over at the end of this week, so perhaps without that stress, we can have some good times uninterrupted by this. I confided in a friend who believes it will all be okay, but I must admit I’m feeling scared for the relationship. I know every one is different, but this feels like a lot to be dealing with so early on. A part of me is honestly convinced that it is doomed, though I know I am catastrophising.

    Thank you both for your kind words and advice, they have been of great help. Jalene – a note on the insecurity thing. Congratulations on your realtionship, I can only hope to be so successful in my own love life. Part of my views on insecurity are no doubt informed by toxic masculinity, which I am not a fan of, but which has nonetheless been hammered into my ego through my upbringing. Sadly, a great deal of shame still follows my efforts to be vunerable. Recently I have confided in my girlfriend and a few of my friends about various difficulties I’ve had, and I feel doing so has only weakened me somehow, perhaps my image of myself. It is very strange.


    Hi Shaydee!

    I’m glad that talking to your girlfriend brought you closer together. It sounds like she has her own anxieties too. It’s good that you reassured her. It tells me that a) she cares about your relationship b) she’s under a lot of stress c) she trusts you enough to express her concerns d) she may have had bad experiences in other relationships. I hope as the stress calms down things will get easier for you both.

    Another way to think about being vulnerable is about being authentic. Sure, you’re not relying on an image anymore. But being authentic gives people the chance to love you wholly for who you are. Surely this is better than only a small piece of you being loved and being too afraid to share more than that with others. Every single person has weaknesses. The question is how brave people are in being open about them. Of course there is a time and a place. You don’t have to share all of you with everyone. But it’s nice to be able to be with loved ones wholly.

    Wishing you both all the best! 🙏 Proud of you for having some healthy conversations.


    i have no idea why she had a 3 way , but have you considered that it may have happened because she had not had a boyfriends before, and just wanted to feel accepted. i personally am not going to have a 3 way because im not into some creepy couple that cant be in a relationship by themselves and need to drag some other chick into it to get off.   why is the girlfriend not enough for the boyfriend? why is the girlfriend okay with sharing her boyfriend , why would she be okay with her boyfriend needing to be sexual with someone else , and make her participate ? i could be completely wrong about the motivations of this but personally i feel that a young female without any real relationship experience , likely had/has little self value , or maybe does not have the courage to say she isn’t interested, and ends up doing something that she may not regret at the time, but  eventually may impact The future connection with someone who wanted to care . its hard to respect someone when you know that they haven’t respected themselves, but maybe this is not the positive experience that they are all making it out to be , maybe they don’t know how to form healthy attachments and mix in the influence of todays   everything goes culture. maybe people end up doing things that might feel good then but with time and maturity are not something they are particularly proud of or would do again. and i am not a prudish person by any means. but in my personal experience , sex with out feelings or emotions feels like your being used, amd it really only takes 1 or 2 times for you to be able to KNOW this. so if you keep doing this , you are kinds a sell out, wich in turn lowers your value , cause if u are willing to have someone touch your body and touch theirs in return that , you cant claim to have a real connection or desire to be with , then the only reason your doin is would to gain something rite?  what is the gain what was the price for you self respect and your body ?   none of this is specific to this situation , they may have completely different mind settings than me , but if she had similar thoughts, the fact that she did it is not the bad thing, it would only be bad if she feels similar and continues the same behavior.  if it makes u feel dirty , then lesson learned , now she knows what not to do and u cant hate on that but f she feels dirty but continues to repeat the same actions with the same or other people whether it be a 3 way or not so casual for her only sex, then she may have some attachment issues that are not your problem unless you want then to be, having said that , Goodluck  finding someone who had not “sold out ” or has healthy attachment style.   lol that was not very helpful hu? sorry , hopefully i was able to put into text what i wanted to get across ,i have difficulty doing that most times. i think I’m trying to say , if she does not feel good about what she has done before, but now knows that she does not want to pursue that again because she has experienced good with you , then you should try to forget it little harder, but if she has negative feelings about what she has done and continues that behavior , its a cycle that is not gunna stop until she stops it. on the other hand if she feels no negativity , than that is just how she feels and you cant fault her for it but maybe your values are misaligned and no amount of trying to make it work will fix that. for reference i am 30 female and just married my bf of 9 years  soi may not relate yo your age and life  .   hope you figure out something that you can be happy with  i say this alot but seriously look up  attachment styles and get insight on why you form the attachments that you do .

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