I'd have no problem with him being a Boy George. I always used to say if he does, he could do my hair.
Then my hair started falling out. WTH?
I do think he needs to get back in the saddle, so maybe that earlier idea you had would do the trick.
Originally Posted by: zombieslayer
How about taking him on a bus ride. Just a short one. Let him sit next to a girl of his choice and let him talk to her for a while. Just a short while, nothing too long. If he's even slightly more interesting than a sack of potatoes he'd have a great set-up for asking the girl out. Just getting over that first hump, getting out there and starting to talk and ask her out, that's the biggest problem, usually.
Because really, there's no 17 year old in the world who's tired of sex. It's just that, when you've been out of the saddle for a while, it all seems like such a huge effort. It's easy to go to another outlet in that case.
He'd actually be building towards something, he's doing it on his own power, so it'd be a huge confidence booster and it won't cost you anything more than a busticket.
I hope you're being sarcastic about the prostitute idea, btw. I'd die of embarressment if my dad bought me a hooker. That's a trauma-builder right there. It's a pretty fucking retarted idea, by all means.