I admit, I'm totally confused. He flirts with me sometimes, calls me beautiful and says "you really are hot, Sam, even if you don't realize it", we talk on the phone until the early hours of the morning (we fall asleep talking sometimes), says I'm probably the sweetest girl he's ever known and out in public, I guess we look and sometimes act like a couple.
But then he talks about how hot/beautiful other girls are with me, said once he doesn't want to ruin our friendship by going out (I guess I'm always the friend he falls back on when a relationship fails), and once we even made the deal that if we were single at 40, we'd get married (haha).
Are we -just- best friends, or is it possible that there's something more there that he's hiding?
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Don't worry, he's got me confused, too.
He can't be that clueless not to realize that he is sending you signals, but then to talk about other girls when he is with you doesn't make sense. Has he dated other girls off and on while you have been friends? If so, perhaps you are right, and that he is comfortable with you, likes flirting with you, but values the friendship more than a possible dating relationship.
I'm assuming you wouldn't mind more than -just- friends. Perhaps he doesn't realize this? Perhaps he is trying to protect himself from rejection by not making more of a move?
What if you tested the waters a little bit to show that you have some interest, just to see what his reaction is... if you said something about when he talks about other girls, the flattery he gives to you seems less meaningful. Or if he comments on ruining friendship by going out, say that some things are worth the risk. These comments aren't really commitments on your part, but more of a nudge to get him off of the fence.