What to do with someone who flirts with you and rejects you at the same time?

IntoNothingness asks: There is this senior guy at my high school who was looking for a girlfriend. We have a mutual friend who suggested that he could talk to me and that I was single. So we started talking. We became really close. He even told my friend that he was interested in me and if she could help him ask me out. I also liked him and we both kept dropping hints that we were attracted towards each other. I don’t know how or what happened, but suddenly this guy shuts me out of his life and I come to know that he has a girlfriend. After some time we started talking again and I tried to be a really good friend. He told me every personal detail like a very close person in his life. We talked and flirted on a daily basis but I kept it friendly as he had a girlfriend. He started dropping hints again and then out of the blue breaks up with his girl. Sometime after this, we had a friendly/romantic meet up at my place and he kept being like “you are single and now that I am single, you know…” His hints were very obvious and I really thought that he was interested. Day before yesterday, we were talking and he was being very flirty and the way I was talking anyone could have guessed that I might ask him out and he was also encouraging the conversation. I asked him out and he went completely blank. He literally told me that he liked me a lot but not like that. We were so close and comfortable with each other but things just became awkward. I am fine with the fact that he does not like me like that but what hurts me is that he never felt anything and still reciprocated every feeling and also gave hints. I would have been very happy had he honestly told me that he never felt anything for me rather than fake reciprocating and that we could only be friends. I invested a lot in our friendship and he didn’t even care about our friendship and let things become awkward between us. Our friendship was really special for me and after our embarrassing “asking out moment” I was the one who tried giving it another shot. But now I feel like I shouldn’t have. Am I portraying myself too available or desperate or vulnerable to this guy? Is giving our friendship another shot wrong? What is the mindset of the guy – like why did he do this? Why did he give hints and talk like that when he clearly felt nothing? Was our friendship also fake?

Hi IntoNothingness –


Okay, so I am completely confused.  Just as I’m sure you are!


So this guy told his friend he was interested in you, then started dating another girl, then broke up with her and flirted with you, talking about how you were both available, but then, once you asked him out, said he wasn’t interested in you.


So I see two possibilities here.  And either or both are possible.  First, he’s just playing with you, completely aware that he’s toying with your affections, which for some reason seems like a good idea to him.  Or, second, you’ve been misinterpreting him a lot.


Now you ask a bunch of questions – about whether you were too “available” or not, about whether it would be right or wrong to push for that friendship to continue, about what his feelings are.

But I’m going to suggest that you put all those questions aside for a moment, and instead ask yourself one giant question: given the way things are now, what do YOU want?


You see, it’s like when I was in the pound.  All we pups cared about was someone wanting us enough to get us out of there.   I lucked out and got a wonderful human; others got less-great ones, and of course some others didn’t make it out at all.


But you aren’t in that situation.  You’ll live through this, no matter what.  So while it’s interesting to wonder what he’s thinking, or if you could have done a better job of playing the romance game, the truth is that this guy has made it clear he’s not interested in you, while you’re interested in him.  And there’s a really good chance he’s been playing with your feelings.


So, if you liked yourself as much as I like you (and all my pack members), what would you do?  Would you maybe give this guy some space and see what he does?  Or maybe tell him off?  Or maybe look for a boyfriend somewhere else, and then, once you have one, see if you still want to be friends?


You see, all of those get back to the question of what YOU want.  And letting him deal with his odd feelings himself.  And I like that.


And what if you say “But he’s the only person I’m interested in, and I want to try to make it work with him any way I can?”  Well, then I’ll cheer you on.


But even if you do decide that, I’ll hope that you can keep yourself from saying his feelings matter as much as, or more than, yours.  Sure, his feelings matter.  But yours have to matter more.


They sure do to me.


Whatever you choose, BEST OF LUCK!


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