I'm planning on taking a girl out for some drinks and then challenging her to a game of foosball to settle and old debate we have about who is a better foosball player when we're drunk. These challenges are always more fun when there is some type of wager involved.

She will probably want ice cream if she wins, but I was thinking of taking my reward to a higher and more risque level. Providing things are going well and we are both having fun, do you think it would be too forward to ask for a kiss or boob flash if I win? I almost prefer the flash option because its more funny and suprising, and if she agrees you know she's awesome.

Any other ideas? I was thinking a shoulder massage for me (booring), a dance (ie: other date, fun but nothing I will enjoy on this date), or a lap dance (very cool, big risk big reward situation).

I think you should go ahead with the rewards you already wrote down there. A kiss is fine and flashing is great too.

At the very least those will get a laugh.

WOW you created a count for this problem. this is a no-brainer. man if everyones women problems were only this easy.

I guess I'm wondering how to escalate without being too sleazy.

I don't want to come off like one of those sleasy douches who hits on a 10 who won't even look at him, strikes out, and spends the rest of the night at the bar repeating, "Where are all the hot chicks at?" as they dance all around him, oblivious to the sad sack he is.

So enlighten me to the no-brainer good sir!
Ok, maybe I'm in no danger of that, but I usually escalate slowly but constantly until she can't stand waiting any longer and attacks me. It doesn't always work, but when it does the girl turns into a hurricane of sex and nothing is off bounds. I would like to start initiating contact myself, and it is new territory for me.

Enlighten me to this no-brainer sir!

Just go for a kiss, then give her an awesome kiss. That's what I'd do.

keep mentioning what am I going to get if I win. maybe what she wants will be worth losing for. flirt around and talk to her and then see how its goes.