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How can you not see what's wrong with putting down your friends in order to chase tail? Do you only feel morally obligated to be kind and considerate of the people you are romantically interested in?
His comment was still pretty rude even if he did not know she likes him.
I don't know why would you go out with an asshole like him, or even call him your friend, let alone having a crush on him.
What kind of friend so blatantly puts you down like that? Not cool
What kind of girl would accept a date with him after hearing how he treats his friends?
You could do much better than that asshole. I know it's hard to move on when you care about someone but he's not worth a single second of your time.
I hope she turned him down so fast his head is /still/ spinning. What an absolute knob.
What happened afterwards? Did the waitress give him her number or did she stick up for you?
... And that's when you ditched him with the check and the waitress turned him down for being a shallow prick. This guy doesn't deserve your friendship and is definitely not worth more.
Who the hell does that to someone? Especially a friend. You don't deserved to be treated like that, OP.
I imagine the waitress thinks pretty poorly of him....what sort of an asshole does that? (I've had crushes on huge assholes before, trust me, when the spell breaks, you will feel relief whenever you think of dodging that bullet!)
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What kind of friend so blatantly puts you down like that? Not cool
I don't know why would you go out with an asshole like him, or even call him your friend, let alone having a crush on him.