Want to play cards?
If you’d pay that much money to see a woman strip, then you’re a sucker. And she’s not your “friend” because you obviously see her as a stripper. I don’t know how this question can be serious.
Nobody’s going to just hand you a hundred dollar bill for being naked.
I stopped at the bank and got a hundred singles.
Guy and I find it very very creepy.
From Love My Rifle More Than You by Kayla Williams (a woman who served in Iraq).
Bet that Chicago Dopefest this weekend is looking more tempting now, huh? 
I have the cards. You bring the tequila. 
I think Priceline just broke under the pressure of 2000 Dopers trying to book flights into O’Hare all at once.
WhyNot, between you and HazelNutCoffee, I have no doubt.
Anyway, this is creepy. I’m not casual about nudity, but I’m not generally modest either. And I’d be very offended by an offer like this.
Another guy. Creepy.
I’d find it far less creepy without the offer of money.
Yeah, the money thing is creepy.
Basically, you should say “May I please see your tits”.
I don’t have flirting relationships with my friends. I certainly wouldn’t be friends with anyone who would offer me money to be naked for them. That’s creepy. On the other hand, most of my friends have seen at least my tits. 
You just need to hang out with people who aren’t in it for the money.
Socially retarded and creepy. I would spread the word to all my friends.
It’s the offer of money that really bothers me. I can understand wanting to see a friend naked. But offering cash as though it’s a purely business relationship? A woman displaying her nudity to me for money is a stranger involved in a deal. A friendship is something special. Turning it into a financial situation is a horrible thing. Wanting to see a friend naked isn’t unusual. Asking to see a friend naked is acceptable under certain circumstances. Offering money is a good way to ruin a friendship.
I agree, the money angle is what ruins it. Bartering something more mundane is less creepy. Example-
Years ago, I had a friend who I wanted to see topless. We had dated early in High School but it never got beyond kissing so I was always curious what she looked like in that area. She of course knew this and was always teasing me about it.
One night we were all at Denny’s and she wanted to play the claw drop game, but she didn’t have any money. I had a dollar and told her that I’d give it a shot if she showed me her boobs if I won something for her. She agreed.
So I ended up seeing her boobs in exchange for a $1 Plush Gorilla. Best trade ever
Well, it wasn’t all that creepy. However, I’d say you lucked out (she probably should have slapped you) and possibly missed out on more than you realize when it was all said and done.
Depends. I’ve done some modeling, so “Hey, I need a nude model for a project. Two hundred bucks for the day okay by you?” wouldn’t bother me. It’s also a bad idea to dare me to do something relatively harmless unless you really want me to do it, so “$50 if you flash the rest of the party,” would also merit some consideration. (Actually, there are circumstances under which drunks shouting “Show us your tits!” would get me to take my shirt off. I enjoy watching the pandemonium that ensues when I do something like that in an entirely blasé manner. :D) The key here is that the person waving the money is acknowledging that this is some sort of unusual situation, and you do not go around randomly offering your friends money to see them naked like this is part of their normal everyday lives.
Also that the person offering is not skeezy. Skeezy creeps do not get naked-girl-viewing privileges from me.
See, something like that wouldn’t creep me out as much. I might even agree to it, depending on how drunk I am. It’s the thought of someone, after obvious forethought, deliberately offering me money to see me naked that I find disturbing. Something spontaneous like a bet wouldn’t bother me as much. YMMV, of course.
I agree. A bet or dare or joke are all things friends do, so that’s not creepy. A premeditated business proposal is creepy.