I know it would seem more worthy if it were to win a barroom wager, or to get through a turn of Pictionary....

You don't want much, do you?!?!?

Let's review-- you want the lady to win him at poker, AND you want him to win HER at Pictionary?!?!?!? In a Western?

AND she has to be respectable? How about merely redeemable? :~)

That would be La Femmme Nikita. (French version.)

~Susan