Have you seen the documentary "My Date with Drew"? If not, you really should. Netflix recommended it to me (since I adore quirky documentaries), and they were right on.

"My Date with Drew" is a 2004 documentary film starring Brian Herzlinger. Armed with the $1100 he won at a game show and a video camera, he attempts to get a date with Drew Barrymore.

Since I'm $100 bucks short of Brian Herzlinger (and probably not nearly as charming), I would use my $1000 to go after a lower tier celebrity. He probably couldn't be an A-lister anymore. And it'd probably have to be a tv actor who never, really had a successful film career. And his 15 minutes of fame would probably have to have been up like 15 years ago. *thinking... thinking*

I GOT IT!

If I had $1000 to spare, I would go on a date with URKEL. Yes, Steve Urkel from "Family Matters". Those glasses! Those suspenders! That laugh! Geek chic doesn't get any better than that.

Yes, folks, you read that right. I would pay Urkel $1000 to go out with me. For the low, low price of $1000 I would have a LIFETIME of bragging rights.