I recently went on a date with someone, but I also have this man who I am friends with always make jokes about how he's gonna fight my date or asking me what he needs to do to win me over. There are lots of statements like that, but all in a joking manner.
Is he really actually joking? Or does he like me?
Is he really actually joking? Or does he like me?
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Difficult to say... but I'm leaning towards there being SOMETHING behind the constant joking comments along the same line. I mean, an actual friend isn't going to make those jokes often enough to seem weird to you. Which... is why it seems weird to you. I would suspect he likes you.