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Who would you play strip chess with??
The selection should be mathematically weighted in regard to risk and reward.
That is, the greater you increase your chance of getting a stunning beautiful woman, the greater your risk of getting an ugly shocker.
The maths could work like this:
low risk = 80% chance of getting a pretty average girl next door who isn't that great. For instance Kirsten Dunst would be in this category. The other 20% wouldn't be that bad either. Say some washed up ex star like Olivia Newton John.
Medium risk = 50% of the above with slightly prettier or uglier women respectively.
High risk = 20% chance of getting an absolute stunner like Jessica Alba or Jennifer Love Hewitt. But the 80% chance are total shockers - 80 year old, wrinkly, denture-teethed bitter divorcees who would cut off your proverbials without a thought.

I choose the woman with whom I have a discreet romance. I tried to teach him to play but we need to focus more on it.
The Kosteniuk/Pogonina match would be interesting to say the least, but it would be even better with more chess hotties on that stage. There are enough chess hotties today to make any man confused regarding where he should place his attention!
As for the selection of a chess-dumb opponent for myself, I'm torn between a couple of local options and a variety of actresses who are now either starting to get too old for this (like Angelina and Charlize) or not quite as hot as those two used to be. I have a hunch that Mila Kunis looks better with clothes than without them, but I'd be happy to be proven wrong. I think I'd go local--especially if Mila continues to ignore my calls.