Disclaimer: I’m probably being petty.

So, I (25F) have been friends with this guy (25M) for about 6 years. We know each other really well, lived together at college, still hang out all the time etc. We have never dated and afaik neither of us ever considered that. Like a brother-sister thing.

He recently got a new girlfriend who seems really nice and I’m very happy for him. However, the last few weeks he keeps making weird digs at my appearance, just going on about how much better looking his gf is than me and how I have flaws she doesn’t and how she shows me up when we go out together. Not even as part of a conversation, just out of the blue.

It started as like a bit of a joke about me being less girly, but now he’s just started being nasty. It’s not just in front of the gf either, like trying to flatter her, sometimes it’s when we’re just by ourselves.

I’ve told him to stop it because it kinda hurts my feelings, but he just says he’s only teasing and does it again.

I don’t know if I’m overreacting or if he’s being insecure or if she’s put him up to it because she’s jealous?

Why is he being such an ass? And how do I get him to take me seriously when I say stop? (I am not very assertive).

Sorry again if this is petty and stupid.

TLDR: Very close friend of 6 years won’t stop making rude comments and comparing my appearance to his new gf.
Why?

33 comments
  1. Maybe trying to make sure he has no romantic feelings for you? Doesn’t sound like a good friend tho if he’s hurting your feelings on purpose.

  2. Instead of just saying stop. Ask him whats up, whats changed? Tell him this is unacceptable and counter to how he used to act. She may not have put him up to anything he could just be trying to treat you just like one of the guys and is over correcting.

  3. OK, this reminds me of a few jokes Chris Rock would say

    1) A man doesn’t have female friends, he simply has girls he hasn’t fucked *yet*

    2) Men don’t friendzone girls, you never hear a man say “Damn that girl is FINE, she’s so fine I’m gonna make her my friend!”

    Now obviously it’s a joke, all men aren’t like that.

    But some men ARE.

    Based on his behavior, I suspect he’s had a thing for you for a LONG time and never had the courage to say it. He just HOPED you would see how he was always there for you, and your friendship would turn into love. But never had the courage to say anything out of fear of losing the part of you that he DID have.

    So now that he has someone else, he’s a little bitter that you never saw him the way you hoped he would.

    But a part of him still wants you, so he’s trying to make you jealous.

    There’s a fine line between love and hate, and while I’m not saying he hates you, not even close, I think now that he has someone he’s being a bit spiteful to the person he wanted who didn’t want him back.

    Tell me… is this the first girlfriend he’s had for more than a few dates? At least since you’ve been “close”?

    If he has had others in the past, has be acted “off” but you just chalked it up back then as “he’s busy focusing on her” but might have been a little more mean-spirited, in hind-sight?

    If it IS his first girlfriend since you’ve been close, then I imagine as soon as they break up he will be back to his old self, still being the best friend you can imagine, still silently hoping you will see him as the man of your dreams someday

  4. “Hey bud, you’ve been making a lot of cracks about my appearance lately and it’s pretty mean – especially since I’ve asked you to stop. I know you say it’s just teasing, but regardless I’m telling you it’s making me feel bad, so can I trust that as my friend you don’t want me to feel bad and you’ll cut it out?”

  5. Tell him that next time he does it, you’ll leave the conversation and won’t talk to him until he apologizes. He probably will tell you that you’re overreacting and he’ll do it again. At this point you just have to follow through and leave and no talk to him if he doesn’t apologize.

    Maybe he always was an asshole, maybe he grew into one,either wat he is one now, and you won’t get anything good from being friends with assholes.

  6. Dude STFU you are being an asshole…

    I was just teasing…

    No you are being an asshole.. it isn’t funny.

    EVERY SINGLE TIME.. until the friendship ends or he stops.

  7. Personally I think he wanted more with you and now he’s being a jerk because he still prefers you. But that’s neither here nor there. Set up your boundaries, tell him to stop and if he doesn’t then stop hanging out with him as much. Despite the reason why it’s happening it needs to stop.

  8. Calling him out is a good suggestion but if you’re not quite ready to do that or if you don’t want to give him the reaction I suspect he is looking for, you could always respond to comments like “[Girlfriend] has [physical feature/style] you don’t” with a very bright and cheerful, “well good thing she is your gf and I’m not!” just over and over again. He’ll either get the message or, more likely, he’ll get upset enough to ask you why you’re acting like that which is the perfect time to counter with, no why are YOU making so many negative comments about my appearance.

  9. It is incredibly hard to understand why he’s saying this shit without fully knowing your characters, relationships, and major life events.

    But here are a few theories.

    1.) This isn’t about you, it’s about him really trying to convince himself that his girlfriend is better than you. Unbeknownst to you, he might have had some feelings for you in the past and being in a new relationship now is causing him to wrestle with those feeling.

    2.) For whatever reason he feels he needs to bring you down a peg. Maybe this is kinda like revenge for something that happened in the past? Where you might have unknowingly made him feel bad?

    3.) He feels inferior to you in some way, so this is how he levels the playing field. Like, maybe you’ve been more lucky in relationships than him for example.

    4.) This is his way of trying to make you jealous. For you to see how valuable and cool he is for landing a hottie gf. A weird way to try and get you to feel for him.

    ​

    How to get him to stop? You can either be extremely vulnerable or embarrass him.

    “Friend, listen. When you keep talking about my looks it actually really hurts. Nobody likes to be put down all the time like that. I don’t care that you’re “just teasing me”. It freaking hurts. Stop, or I’ll have to cut our conversations short.”

    or

    “Why do you keep talking about my looks all the time? It’s creepy. You have a hot girlfriend and yet you keep bringing up minor details on my face? It’s like you have a crush on me or something giving my face that much attention. Jesus christ. Get a grip.”

  10. Does he want *you* to be jealous? Was he carrying a torch for you and now that he’s in a relationship wants to rub your face in it?

    He’s being a shitty friend, whatever his stupid reasons.

  11. It’s probably because he’s had a crush on your for years and now he’s got a girlfriend he makes a point of teasing you to get back at you for not picking him.

    Or she’s jealous so he’s doing it to make you feel like shit.

    Either way I wouldn’t wanna hang around someone who’s like that. I’ve had the exact same situation and I’m better off without my “friend.”

  12. Hold on why are you still friends with this guy? Everyone telling you to drop him is absolutely right. If you were vindictive like I am, I would tell his new gf what an ass he is about your appearance. Poor thing should be warned about the type of person she is dating.

  13. He’s attracted to you and his GF knows this and he doesn’t know how to handle it so he projects this by saying things to tear you down/humble you as a way to convince himself that you’re nothing special.

  14. >he just says he’s only teasing and does it again.

    This gets into the realm of being deliberately hurtful. No, you’re not overreacting.

    > how do I get him to take me seriously when I say stop?

    Walk away. Seriously. Boundaries only hold if YOU hold them and the only behavior you can control is yours. If requests are blatantly disrespected, the next step is to remove yourself.

    E.g:

    “Don’t talk to me like that.”

    “Oh, I’m just teasing you, you oversensitive ugly girl.”

    “Okay, we’re done here, goodbye.”

    It may get to the point where you just need to tell him you don’t want to hang out because he won’t stop needling you and you don’t want to be in that situation. (He’ll tell you again that you’re overreacting, but he doesn’t get to decide how you feel or should feel about his hurtful behavior. That’s called gaslighting; denying your reality until you doubt your own mind.) It can hurt to cut people out of your life, but if it hurts you to be around them, getting away is a better long-term option.

  15. It almost sounds like he’s trying to make you feel like you’re “missing out”, like “oh just so you know I’m out of your league, peasant”!

  16. First things, first. Do not gaslight yourself. You’re not being petty. His are hurtful comments. You’ve communicated to him directly that this hurts. Bravo for not taking the passive-aggressive route of simply disappearing/ghosting/etc. He, on the other hand, appears to be acting towards you in a p-a manner. Rather than telling you, directly, what’s eating at him, he communicates, rather ineffectively, via the p-a route.

    But, his issues could be something else, and it may require just the 2 of you hashing this out. You’ve identified the symptoms–his hurtful comments. My intuition is you need to dive deeper. Perhaps ask him directly why he feels the need to comment about you as he is. I think you could let him know it’s affecting your relationship, and that he needs to take this seriously.

  17. This feels like negging and the why could be that he is trying to manipulate you into competing with his gf for his affection. At any rate, I don’t think he is a very good friend and I recommend distancing yourself

  18. Sounds like he either had a thing for you or still has and is trying to flaunt his girlfriend to show either that he can do better than you cause he’s annoyed you didn’t get with him or to make you jealous. Either way he doesn’t sound like a good friend

  19. Every guy I thought was just a friend in high school and college eventually hit on me. One coworker came right out and said “ guys are only friends with cute chicks.”

    Your “friend” still likes you and is too immature to be your friend. Move on.

  20. You need to realize he isn’t your close friend. He’s a dude that’s wanted to fuck you for years, never had the balls to approach you about it, and is now pissed you don’t care that he has a girlfriend. Cut that freak loose and move on. Don’t let him back in either.

  21. I don’t want to flare up your anxiety but it feels his gf is jealous of you (or is uncomfortable with your friendship) so he’s trying to show her just how uninterested his is in you.

  22. One of two things is happening here, from my view. Either she’s jealous and put him up to it, as you suggested, or u/Thecardinal74 is right and he has always had a thing for you. He perceives his girlfriend as being inferior to you in some way, so in his mind this becomes your fault for being too obtuse to understand that he’s loved you all this time. He thinks it’s your fault that he had to settle for less than he feels he deserves (you). That means you’re an asshole, because obviously he’s SO emotionally expressive and intelligent that there’s no way he could simply have failed to communicate his feelings in a way that you would understand /s.

    SOMEBODY’S insecure here – whether it’s him or her is 50-50, flip a coin odds. It doesn’t really matter, though, because negging isn’t cool. You should consider ending the friendship, or at the very least putting some major distance between yourself and him.

  23. You’re not being petty. He’s pissed because he has feelings for you. He’s being a jackhole because he needs to justify to *himself* why he’s not with you.

    Tearing you down is his way of providing that justification. “She wasn’t pretty/kind/smart enough for me anyway”

    I feel sorry for his gf, actually.

    I’d ghost him for now.

  24. I just went through something similar. My friend of several years has admittedly been in love with me but we never dated, we stayed friends. I’m now married. Recently he got a girlfriend, after their first date he just randomly said “this is who I went out with last night,” (I did not ask) and proceeded to send me a bunch of her nudes. I was like oh nice? Glad it went well? After that, he would randomly message me telling me things they had planned (which is all fine) and then get back into sexual stuff saying things like “the head is unreal, her pu$$y is amazing, etc)

    Very very odd behaviour. Which I can only assume is in the realm of revenge in their minds because they never got what they wanted from you, and so they think they can make you jealous and like, rue the day. Men are odd.

  25. Just a maybe here:

    Maybe he doesn’t want to get his gf insecure.

    Or like others have said, he’s trying to ‘show off’ since he’s got feeling for you but you never reciprocated or never realized.

    Or he wants to convince himself that you are not attractive anymore, this..if no.2 scenario is true, that he’s got feeling for you in the past. But now that he’s with another partner, he wants to convince himself subconsciously that he’s totally over you.

    Since y’all are close enough, I’d be blunt to him, if I were you when he puts you down again, you stop him and say ‘that hurts my feeling again. You used to not be like this. What’s up.’

  26. Thank you everyone for your suggestions and advice!
    I’m meeting up with him and some other friends after work next week and will see what happens.

    If he does it again I’ll be more forceful and explain that what he’s doing is beyond playful teasing and is actually weird and upsetting. If he argues I’ll just stop engaging and ignore him, I see now that it’s not worth my energy.
    I’m not going to accuse him of anything, just explain that he’s being a complete ass.

  27. Tell him he needs to stop punching down to lift his GF up. If she is a decent person, I doubt she would even like that.

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