How are you down a boyfriend? Obviously he isn't interested in you and that's fine. He doesn't need to date you because you are interested in him.

Maybe with his winnings, he can take you for an ice cream or something, then boom! You get the $10 and take him out with the winnings. That’s TWO dates!!!

He either didn't ask because he's not interested or has no clue you would be. I'm guessing from the fml maybe you never said anything? Though the name of the OP is a little worrying. Did you ask? I hope the OP isn't over the age of 25.

It feels good to be back in the game again!

I feel like since he's your crush and you proposed the bet, the only reasonable next step would've been for you to ask him out on a date.

You shouldn't have said "I bet you can't get a date today!" but "I bet you can't get me to go on a date with you today"

You kind of told him to go find someone else and I'll give you money.

I'd be willing to bet he's going to need that $10 he won off you so as to *pay* for his 'date' with said girl...if you get what I mean ;)

What the hell did you think would happen?

I read cousin at first and was very confused.