“Did you happen to bring any cash with you?”
I don’t have a bunch of pre-planned questions because I don’t want the whole thing to be like a job interview.
If the guy has a bunch of pre-planned questions to ask me, I try to get out of there ASAP.
Great tips! Usually when I’m around new people (regardless if I’m in a date setting or not) I’m usually too nervous to think of my favorite so-and-sos. Even if I do happen to locate my favorites, I’m not sure if I want to share them before they share theirs. Being judged inevitable, but the sooner the worse. Also, being somewhat evasive in the beginning, is a good way to be a little mysterious…which is a turn-on for some people.
And please, no crazy hypothetical questions such as “If you had to be an animal, which one would you pick?” :dubious:
Not even “what are you hoping to come back as in your next lifetime”? 
I always ask: If you could do anything you want, free from financial worry, what would you do?
My favorite, “Do you take American Express?”
Well, it’s not something you can ask out of the blue. But I’m a nerd, so I’ve dated quite a fwe guys who could ask such things as “how much of a bonus to ‘scare opponent’ do you get if you have a dragon behind you?”
So, anything about hobbies.
Another nod in agreement to Bear_Nenno.
I don’t think there is anything wrong with having a (mental) list of conversation starters for dates, dinner parties, new cow-orkers, etc. But especially for blind dates or internet dates where you don’t already have something or someone in common, having a conversation starter in mind is essential. Sometimes even the best conversationalists and people who are getting along great stall out for a minute. If the whole date is nothing but a series of questions, then obviously it’s either not a good match or someone’s socials skills need some fine tuning.
After exhausting the obvious topics, I too am looking for some good ones to get the conversation rolling. I absolutely hate questions like “tell me something about yourself you don’t normally tell strangers” (sorry FilmGeek). If I don’t tell strangers, why would you think I would tell you? I don’t like being put on the spot for witty answers. I like witty questions that engender natural conversation, but it shouldn’t be a cleverness test.
Ditto. I hate being put on the spot. Then again I don’t go on blind dates, so I always would have something to talk to my date about, even if we’re just making fun of mutual friends or remembering TV or something. I guess my conversations are pretty lame.
Conversation flows pretty naturally if the person is at all interesting. So my favorite questions are ones attuned to the specific person I’m talking to. I would hate to ask/answer blanket questions.
Of course there’s the obvious one:
“Did you bring any condoms?”
“Can I touch those, are they real?”
Ernie or Bert?
Oh, I see, thanks
That is a shame, because I usually ask:
If you were a rock in the proterozoic era, what kind of rock would you be? 
“Is that infectious?”
“Did you find Jar-Jar as annoying as I did?”
“Is that your real hair?”
“Do you swallow?”*
“Why are you shouting at me?”
“Would you like to pet my monkey?”
“What’s the strangest thing you ever ate?”
“Leave here often?”
“What’s your grandmother’s brother’s wife’s third daughter’s sign?”
“Have you ever dated a sex maniac before?”
*shamelessly cribbed from Me, Myself and Irene.
This thread reminds me of something I read about Bill Gates a while back…
They said that Bill didn’t date much in college, but when he did, he always asked his date what SAT scores she got, just so he could mention what *his * (very high) scores were.
<<Miss Rhode Island, please describe your idea of a perfect date.
That’s a tough one. I would have to say April 25th. Because it’s not too hot, not too cold, all you need is a light jacket. >> /Miss Congeniality
Thanks for the tips, especially Bear_Nenno!
As mentioned, it’s great to simply have an idea of a few fun questions to throw out there whenever the conversation lulls or hits a slow spot.
Of course, you don’t want to come off like you’re giving a job interview, but I love to have questions in mind that will help spark up conversation again without putting the person on the spot and/or uncomfortable.