How would you deal with an awkward situation involving a friend and a significant other?

Here goes my opinion
First I think your right, alot of time men do not take female/female relationships serious.
Second I think you should not worry, if your friend does not think he is hitting on her, maybe it is just joking around. You said he has known her longer.
Next time, if there is one, that he hits on her in your opinion. Just ask him if he is hitting on your girlfriend, then say you don’t like it if he is. Then wait to see how he reacts.
It could be that he really does not realize how his words are being interpreted by you.

Let me get this straight and correct me if I’m wrong because a big wall of text the details of a question is sometimes off putting to me but: you have a friend/acquaintance, someone you apparently don’t really have that close a relationship with and he keeps hitting on your girlfriend? And your issue is how to deal with the “awkwardness?” Someone repeatedly hitting on your girlfriend is just a “pet peeve?” There’s this guy you occasionally go to the movies with who hits on your girlfriend in front of you because he might not respect the fact that a lesbian relationship is as valid as a heterosexual relationship and you’re afraid of hurting his feelings and guilty about not R.SV.P.ing to his Halloween party? I must be from another planet or something, I guess. I just never get these things. Life is too short and too precious to keep people in your life who undermine you rather than support, uplift or at least tolerate you and cause you no harm. Except for family; you’re kind of stuck with them.

You pick up the phone and tell him that you’re serious about the girl, and that you think his hitting on her is disrespectful of her and to your friendship, and that if he does it again, you’ll punch his lights out.

Is this person a friend of your girlfriends? Is that why you’re worried about it? Cause otherwise I’m with @lillycoyote. Life is too short to waste your time with this sort of thing.

Why are you so worried about what a mere acquaintance, one who does not behave that well, feels?

Cut the guy off. Don’t go anywhere with him.

Side note: If your girlfriend does not take notice of how you feel about him hitting on her and discourage him, I would begin to wonder about how much she cares for me.

Maybe it’s just me but texting, pm’s and e-mail is not the way to be addressing highly emotional issues such as yours. IMO best handled face to face or at the very least on the phone so there is not misinterpretation of intent of message. Texting is way too impersonal for these issues. Stand up for what you believe is right and tell it too their face…much more effective.

He is a friend of my girlfriend’s which is why I was worried. He also considers me to be a close friend, when really I feel pretty distant towards him. I suppose he’s socially awkward?

He used to hit on all the people at movie night (3 girls and him make up the group including me), but he didn’t want to lead one girl on (he thinks she started to like him, who knows), he doesn’t hit on me when my girlfriend is there (ironic?), and so my girlfriend’s the one left to hit on. I felt like it was more my girlfriend’s place to say something, but since I’ve mentioned it, it hasn’t happened again for her to say something to him. I just happened to mention it first in that text to him this week.

I’ve also had problems dealing with aggression in the past (cutting the person out of my life without thought, so I’m trying to be more sensitive as a mature adult, I guess, anticipating the consequences). It would also ruin movie night, which is pretty fun, I look forward to it after a stressful week of classes. I’ve communicated to her that I can’t date someone who doesn’t say anything when someone hits on her in front of me often. I’d rather break up than deal with disrespect, no matter how much I like the person I’m dating. It’s just not worth it. She’s really into me, so we came up with a plan if it happens again. The thing is, it hasn’t in a while. I just have a feeling it would if I didn’t say anything. I’ve tried to change my perspective, but there’s nothing amusing to me about it, except that I’m the one with my arm around her. He’s actually a really nice guy, just lame/awkward/immature sometimes.

She’s known him a while and seems to think of him as a bit of a joke, I think, in the romantic area (he’s the type of guy that hangs out with his mom often and has few friends), so my feelings were a surprise to her, she told me that he can’t hold a candle to me, and I should just feel bad for him.

I’ll talk to him about it in person if necessary. It’s just nice to have second opinions. Thanks all. Anymore advice is welcome.

Lillycoyote, your view is refreshing. That’s how l’ve been feeling. Because he’s my girlfriend’s friend and it would ruin movie night if I gave up on him, that’s the only reason I’m even trying to be careful.

I’ve had bad reactions standing up to people before, but now that I’m at college my self-esteem has gone up a ton and it’s easier to see more clearly.

@Auxilium Well, if the guy is a friend of your girlfriend’s then, I think you’re absolutely right, she should be the one to deal with this. If she knows that it bothers you then she needs to “man up” so to speak and tell the guy to stop it. It’s not your issue, I don’t think. If she knows that it bothers you and she doesn’t care that it bothers you then your issue is with her, I think.

Or… you could take some kind of no nonsense, Loretta Lynn type approach. There’s this scene in Coal MIner’s Daughter where she comes out at the end of a show and finds her husband in the back seat of a car with another woman. She looks dead at them and says “Woman, if you want to keep that arm, you better get it off my husband.” She just sailed right past the awkwardness and took care of business. :-)

Thanks all for the advice.

It sounds like such a big deal in text, but it’s hard to “send” serious (or lack there of) or awkward vibes of a situation over the internet.

I texted him like I stated, and I’ll talk to him in person if I feel like it’s appropriate. I probably will need to if I want to keep his friendship. My girlfriend knows that I can’t date anyone who doesn’t say anything when they know someone is hurting my feelings, though me saying that hurt her feelings, which I felt bad about, though at least I made myself clear in what I’m alright with.

I don’t think that she doesn’t care that it bothers me, I think she just wishes it didn’t because I suppose she just finds it flattering and not a big deal. It wouldn’t be a big deal if the guy actually went on dates with women—if he didn’t think of me, my girlfriend, and the other girl as his only friends, and if I didn’t feel like he was homing in on mine, all be it jokingly and drunk. He’s been nice to me otherwise, just maybe desperate and not realizing that I took it personally. If it only happened a few times, it wouldn’t be a big deal, but it got to the point where it annoyed me.

I think people tend to avoid awkward situations as long as possible, that’s probably why this has even been an issue. Confrontation tends to be awkward.

Though I’ll happily be single if this doesn’t stop. X_X I’d rather just focus on my grades than deal with people that aren’t willing to consider how I feel.

Sincerely,
Not used to Dealing with the “Jokingly” Desperate, Subtle Guy Friend