While there are plenty of questions that should never be asked on a first date, if I had to pick one it would be:

 "Is it two or three month's salary that you're supposed to spend on a diamond?"

This question covers the two big no-no's of first dates: commitment and money. Nothing is going to make a guy run for the hills faster than "we" talk on a first date. Avoid questioning him on past relationships, marriage, kids, moving to the suburbs, etc. While I agree that it's important to know his stance on these topics if you're in a relationship, they are not first date material. If the two of you hit it off you have plenty of time to discover everything you want and need to know about him.

Also, please avoid talking about money (how much he makes, how much you make, how much your ex-boyfriend made, etc.). It's just cheesy. While you want a guy you're dating to be employed (or at the very least have aspirations of being employed), first dates are about getting to know what kind of person he is, which has nothing to do with what he has in his bank account. If you bring up money on a first date, he's going to assume that you're a gold-digger. Contrarily, if he mentions he tipped the valet $20 to take good care of his Beemer, you can safely assume you're on a date with a descendent from planet douche-bag.

Your best bet is to just keep the conversation casual. Don't ask any question that you wouldn't feel comfortable answering yourself.

The Trixie is a 32-year-old woman living in the Lincoln Park neighborhood of Chicago. She enjoys shoes, clothes, shopping for shoes and clothes, talking about shoes and clothes, and the pursuit of cute golf attire. She blogs about all of this at www.thetrixie.com