Um... awkward...

So, I went to this thing tonight and I had a very awkward thing happen.

Um, ok, so there's this guy I know through STAG, he's 31 right? And so like he generally makes a lot of in appropriate comments, but you know you laugh at them and make them back and never really think anything of it.

Well... Tonight, I was trying to give him a used cup as a present but he wouldn't take it, so I was trying to like force it onto him and he pulled me into a hug and said "are you sure there isn't anything else you'd like to give me?" and in my head I was like "What the fuck? Here we are talking about cups and you spring this on to me?" and so I said "What?" and he pulled me in tighter so I could sort of um... feel "everything" and he goes "Are you sure there's nothing else you'd like to give me??" and he gave me one of those looks, you know the one. So I said "Uhhh, no." and he goes "Are you sure?" and I said "Yeah I'm 100% sure" and he laughed and pulled away and said "100%? Wow, can't get more rejected than that!" and he laughed again. So I said "yep, all I'm offering is this cup, it's free!" and he said "The other wouldn't cost you anything" and I was like "it might" and he said "no it's definitely free" and I said "no, it would cost me" and he's like "what would it cost you?" and I said "my reputation OOOOOOHHHHHHHHHH!!!" and I laughed really loudly.

Anyways, he goes "oh, that's harsh!" and I said "you've got to admit it was a good one!" and he did and we hi-fived.

So, like that's really it, but why would he do that? We had a perfectly fine friendly relationship, where there was never ever any sort of seriousness to the conversation EVER, and I never made those types of remarks about him.

Why do guys think they can do that sort of thing? Now the friendship, to me, is awkward.