A new type of 20 questions, What would your character say/do? Options

[Eyeless Blond]

One thing I've had a real problem with in non-freeform RP games is that, as your character's skills, attributes, etc. must be finalized before the game starts you really have to get a handle on that character's personality quickly. In many cases I'll start playing a character for awhile, then after about three or four sessions realize that the character's personality does not line up with his attributes and abilities at all, or differs in such a large number of subtle ways that would in the end pretty much necessitate a huge change in the charsheet to bring the abilities in line with the character who embodies them.

I've been thinking of a way to speed up this character learning curve a bit, and I hit on the idea of a situation questionaire. Basically it'd be a number of questions setting up loaded scenarios that help bring the character's personality to the surface more quickly. I'm having trouble thinking of good scenarios, though, other than the most recent one that sparked this line of thought:

1) Your character is approached by someone he/she finds attractive, and uses a fairly lame pickup line on you. In detail, how would you respond?

Any other ideas? Does this sound completely off the wall?