“My boyfriend told me I’m ‘definitely not’ the prettiest girl he’s dated”

My boyfriend and I have been dating for eight months, officially for six. Initially, I didn’t want to enter a relationship and wanted to keep casual, but he did things that made me feel like maybe he’s great. Unfortunately, I’ve had my fair share of bad/unhappy relationships, and though I found him attractive and liked him, I wanted to work on myself and develop a stronger friendship with him first.

At first, we had fun going out. He would be all over me, wanting to see me as often as possible, etc. So one day, I stupidly asked if I was the prettiest or one of the prettiest girls he had seen. He said, “no, definitely not.”

I tried not to fuss about it too much. I didn’t think much of it, because we were having fun. But then, when he stayed over, he would look at pics of nudes etc. when he thought I wasn’t looking. I started to get insecure and asked questions about why I’m not as pretty, and he would roll his eyes and say, “why does it matter?”

I would message him the same when he wasn’t around, and he just became withdrawn and less wanting to talk. He starting getting less warm and less affectionate in public, which I asked about, and he just remarked that the honeymoon period is over. I tried to revamp it by sexting and being as wild as possible in the bedroom, taking him to dinner, buying him gifts, sending him cute messages, etc. But he would just lecture me and tell me to stop.

He also lectured me about how I spend my money in general, and told me what things I should wear and about my diet. I might add he agreed to a BDSM arrangement where he is my Master, but I think he is taking it wrong and just using it as an excuse to tell me what to do at times.

He also used to say only a certain type of girl was prettier, because that’s what he very much likes to look at, and after making him aware that I am insecure about the women in porn etc., he initially said, “I think of you while I watch it, and no, they aren’t the girls that are prettier then you.” And he said confidence is what is prettier in those girls etc.

Seriously I’ve tried everything to spice it up and gain his admiration and attention — BDSM, presents, strippers, even a swingers club. I will admit there was a time for six odd weeks where sex was extremely painful with him, because foreplay wasn’t enough with him and still isn’t. Fingering my lady parts for a few minutes until he is hard is his idea of foreplay, which I have talked to him about, and he’s like, “oh but I’m impatient etc.”

At that time, I went for all these tests to see about the issue, because I was worried he’d leave if I couldn’t perform. There were times he couldn’t keep hard, then would look at nudes when he thought I was asleep, even early on in the relationship.

Anyway, I confronted him about my pain and asked if he’d leave because of it, and he said it depended on how long it occurred for. I feel like I’ve made all these sacrifices for him. I quit smoking for him, cut down on drinking — yeah, I know both are unhealthy — but there’s heaps he didn’t like, all of which I have stopped.

He doesn’t want to acknowledge that he still compares the way I look to these so-called perfect women. Like, the other day, he admitted some of the women in porn are prettier then me, and when we hang out and aren’t getting freaky, he just sits on his phone. I have to instigate conversation, and he barely listens to me, but when talking to a prettier girl, his eyes light up as they talk. I ask him why he’s dating me still, and he says it’s because he loves my insecurity. I’ve even said we can be friends and I would help him get with one of the prettier girls he’d prefer, and he says, “no, I want you.”

He has said I’m smothering, which I guess I have been, though I WOULDN’T be if my mind wasn’t anxious or insecure over stuff like this. I don’t know what to do. I mean, I’m still attracted to him, but my head is aggravated and so filled with worries when it comes to us. He also has mentioned sharing another girl with me in the bedroom, and I wonder if that’s why he wants to keep dating — to have that arrangement. I really really need help please.

10 thoughts on ““My boyfriend told me I’m ‘definitely not’ the prettiest girl he’s dated”

  1. missmeliss25 says:

    This was hard to read. I think you might benefit from doing some research on “codependency”. From what you’ve written, you have completely transformed your life based upon what you think this guy wants. And neither of you is happy. What do YOU want? I don’t want to assume, but I’m guessing that you are in your late teens/early twenties? I really think you could benefit from taking some time for yourself, completely away from a relationship (especially this one).

    Also…think about the questions you ask before asking them…ask yourself WHY you are asking them. Are you asking because you want to hear a particular answer? If so, it’s better to let it go. I don’t care what you look like – you could be the hottest supermodel – I guarantee that there is someone prettier. There always will be, and that is true for everyone. Find your confidence based upon who you are, your values, what you enjoy doing – don’t base it off of how you look.

    Good luck. And for real – this guy is doing you no favors.

    • Anonymous says:

      Me and my man have been together for 8 months at 1st he told me he was a real gentleman who would never cheat on me and when I fell pregnant I found out that he was messaging other women telling them how gorgeous they are but never told me that also few days ago he said to me out the blue that I’m not pretty an that his ex girlfriends are all above me it’s broke my heart and soul and wen I had a miscarriage he was masturbating looking at 17 years old girls wot do I do

  2. Ken Liu says:

    Having given advice to a girl in a very similar situation as you, all I can say is that you are better than this, and you deserve someone better. All of your insecurities about him are true, and that’s why he’s keeping you around, unfortunately. And even if you don’t leave now, he will leave the relationship eventually, no doubt.

    Stand up for yourself and tell him that he doesn’t deserve you.

    Oh, and the other girl I was advising? I suggested that she leave him ASAP, but she didn’t want to. Eventually he left her anyway.

  3. Dennis Hong says:

    We can all tell you to walk away. And I guarantee, that’s what we will all tell you.

    But, I know it’s far easier said than done. So, you have to be the one to make that decision.

    Good luck on this.

  4. Kate Keller-Kriozere says:

    I was insecure in my teens and early 20’s too, so I totally get where you’re coming from. You think you should be an absolute goddess to this guy. He should think you are the most beautiful woman he’s ever set his eyes on, and if you don’t inspire this feeling in him, there must be something wrong with you. You must not be pretty enough. You must not be good enough. Something in the relationship must be deficient.

    The thing you need to understand is that all of that love-at-first sight; one and only desire stuff is a fairy tale. It is utter bullshit. It is not real life. We all internalized this nonsense as little girls and young women watching disney princess movies and romantic comedies where the guy instantly falls for the drop-dead-gorgeous girl, wants only her, and spends the entire movie trying win her affection. These are not real relationships. As someone else said, in the real world, there are always other, better looking people. Looks are not the only thing that matters. Real love is built on finding the right combination of qualities that attract you in a person who doesn’t drive you nuts all the time.

    Get over your insecurities. Find your attractive qualities and rock being you.

    As for whether you should stay with this guy, I would say no. It sounds like he feeds off your insecurity. You’re never going to find your confidence dating someone like that.

  5. Velda says:

    If he likes the relationship because of your insecurity, what are you getting from all of this? You can’t prove yourself to him. He would never let you believe you are enough for him because that’s exactly how he gets what he wants.

    Let me guess: he only seems to truly appreciate you when you’re gone and he’s trying to win you back? And then he distances himself again? Again: it’s only to get what he wants from you. This is not love. Nothing good can come of this for you. I hope you will get out of this merry-go-round relationship, and get some therapy if you can to help rebuild your confidence. You are enough.

  6. Phot says:

    What a dick! Dump him, any guy who makes you question yourself, doesn’t appreciate you and is uninterested in you, doesn’t need to be in your life. You are doing yourself a disfavor, mentally and emotionally by keeping him around.

  7. Sad insecure says:

    I’m going through the same thing. My boyfriend has told me a couple of times that I’m not the prettiest woman he’s dated…also while describing how we met to his friends. He talks to beautiful girls all the time. Holding their feelings and opinions above mine, making me feel second best. It happens constantly. I don’t know why I don’t leave. He makes it seem like it’s me and all my fault I guess. I don’t know what to do. He says he’s madly in love with me but I don’t know if it’s true or even if I trust him. He even broke up with me while he was in Vegas on a batchelor weekend. Help!

    • Constantina says:

      It sounds to me like he has you just to have a girlfriend. To me it’s obvious the reason he broke up with you while that bachelor weekend was on. Most importantly, he doesn’t respect your opinion and feelings, that’s not something you can fix and it’s definately not your fault. And how could it be?! If any woman read your text and imagine herself in your shoes I bet she’ll feel the same.
      My advice, stand up for yourself, dump him. Respect is more important than attraction. Plus you should really get this to your head that when you start having trust issues it can NEVER EVER be you the cause. So he does something wrong too and your mind can’t detect it but your gut warns you.

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