2. If you could sleep with one of my friends, which one would you sleep with?
Men are men; and most men like to have sex; and sometimes sex doesn’t decipher those who are off limits from those who are. Basically, he may have thought once how sexually attractive one of your friends is or maybe he hasn’t (let’s hope the latter). Still that doesn’t mean he would sleep with her if the opportunity presented itself.
This question is probably one of those questions you ask but definitely don’t want to hear the answer to; you will be angry at him and chances are you will look at your friend differently and she will have no idea why.