I'll make this as short as possible. One of my really close guy friends has had an on and off crush on me for the past 2 and a half years. He's one of those guys who pretty much has a crush on any girl who pays attention to him. Now don't get me wrong here, he's a sweetheart and has been there for me when I needed him and I do value our friendship but ever since my girlfriend and I broke up he has been absolutely relentless about dating me. He flirts with me 24/7, hits on me constantly, keeps asking me out on dates, tries to get me alone ALL the time (when he's home. he goes to school out of state) and when we do hang out he is ALL OVER ME. He even fights people for my attention when we're with a group of people. He started this the day me and my girlfriend broke up. I was with my girlfriend for almost 2 years and was (and still kinda am) in love with her and was crushed when we broke up. I keep trying to tell him he needs to stop and just be happy with being friends with me because I'm not jumping into a relationship with anyone (especially not him). It's really irritating the hell out of me because we can't just hang out like we used to. He always has to try and take me on a date or be all over me. The only way I can see him stopping is by coming out to him but I don't feel like I'm ready to do that. Another reason I don't want to tell him is because I know it will crush him and he's extremely sensitive and doesn't take rejection well at all and I don't want to hurt him. I just don't know what to do. Help? :bang:
The only thing you can do is tell him. If he won't listen then maybe ignoring him for a while until he gets the hint. As he's a good friend of yours I would try to make it as gently as possible since you want it to remain that way. He should respect your boundaries and how you feel. Maybe he's just messing around with you but it sounds like he's pretty serious. Either way, try talking it out with him (again, I'm sure you have) and let him know how you feel and that it's bothering you.
I just don't want to lose the friendship and I feel like I will. He's coming home this weekend (today actually) and we're hanging out (along with my best friend and a mutual friend of ours) and our mutual friend who I'm close with told me to wait til after the weekend to talk to him and not to do it in person. I'm just not sure what to say to him :/
At the moment, I feel like this situation is a little frightening. He seems obsessed. I mean, you're a lesbian and I'm fairly sure that over the time you've known him, you would have told him you're not into guys. Getting dumped wouldn't change that. The fact that he's "all over you" and jealous of others who gain your attention aside, the fact that he believes that he suddenly has a chance because you were dumped means that he doesn't really believe you're a lesbian. It was a phase and now that you were dumped, it's over. You need to be firm and tell him directly that it wasn't a phase and you still very much like the company of ladies. Right now, you can't think completely about his feelings on this matter. Don't pussy foot around the issue because he'll just take that as you saying that it's possible. Be blunt and then put out any fires you need to after. I've been in this situation before--surprisingly--and nothing worked other than comforting him bluntly about it. We remain friends to this day, so it is possible to be blunt and keep his friendship.
He is seeming obsessed, yes. You just need to tell him you are not interested in him in that way and that you are a lesbian. I can't imagine he would stop being friends with you over something like that. If he cannot accept that then that is his problem. That's what I would do anyways. Just tell him how it's bothering you. I don't think he'll get mad from something like that. I'm not saying get into an argument with him but just saying it so you get the point across.
Also, add that perhaps, if he cannot simply be friends with you and nothing more, then you'll have to distance yourself from him. Distance helps in situations like this. He seems like he doesn't get the hint, so tell him you're a lesbian (I think you have to in this situation), and that means you're not interested in men. You don't need an obsessed in your face lesbro. You need your space and time and if he cannot be friends you need to get him out of your life for awhile. Perhaps he will back off and find someone else in time.