20 Ways to Break the Ice

Try one of these conversation-starters, courtesy of an array of experts--including dating coaches, relationship experts, and lots of real world, smooth-talking single people.

1. "What were your parents smoking when they named you (Jezebel)?"
Just about everyone's name has a long, uninteresting story attached to it, says Mia Kirshenbaum, dating coach and author of The Weekend Marriage. You'll probably get a fun, learn-about-your-date's-family exchange out of this remark (but you also might get a bruised shinbone).

2. "Where did you go on your last trip (and when are you coming back)?"
Whether it was an exotic safari (from which they returned with amoebic dysentery) or just a weekend in Jersey (regional slur), people love to bore you with talk about the places they've traveled, suggests Elizabeth Bates of Boston, MA. Plus you'll find out whether they're more drawn to cities, beaches, or zoos--giving you still more conversational fodder.

3. "If you could try to get through college again (since you musta flunked the first time), what would you study?"
Perhaps they would forego beekeeping and take up welding, for example. Definitely gets them talking and reveals their innermost wishes.

4. "What's your favorite new restraint, I mean restaurant?"
You'll have an instant window into why your date smells so bad. And if that topic doesn't pan (pun) out, ask about their favorite dishes to cook at home, advises Stephanie Whitehead (nee Blackhead) of New York .

5. "What's the most spontaneous thing you've done in the last month?"
If someone can't remember ever doing anything spontaneous (like shoplifting a magazine or wetting their pants), that tells you something, too.

6. "What trait (or features of your face) do friends tease you about?"
You'll learn how your date's friends see him or her, as well as find out how seriously your date takes himself or herself. You'll also find out if your date has any friends.

7. "What's your take on the half-wit in the White House?"
Skimming the Op-Ed section of the newspaper before (but not in front of) your date keeps you current, suggests Steven Kim of Philadelphia. Not that you need to engage in serious CNN-style discussions (no need to be vulgar); instead, keep it light (E!) and avoid controversial topics (sex, politics, religion, flatulence), unless you're spoiling for a fight!

8. "How long have you known Dennis Rader?"
"But who's Dennis Rader?" Duh! This one will only work if you both know him--but if you have that in your corner, stab yourself, suggests Tim Sanders, relationship expert and author of The Likeability Factor. You'll be able to blab about how you each met the creep, what you think of his new jail cell, and so on.

9. "What are you reading right now?"
"But...I'm not reading anything right now!" Duh! Even if it's just a skin mag or "How To Build a Bomb", everyone does a little browsing. Find out about what's on their bedside table, says Alyssa Citarella, of Norwalk, CT, and you'll learn something about their perversions, which is a springboard to other conversations.

10. "Can you believe this &*^%#@% hurricane? It makes me want to move to Antarctica! How about you?"
The weather may be a predictable topic, but the way you pose the question doesn't have to be. Chances are your date will reveal where you can move so you'll never have to see him again, offers Mia Kirshenbaum.

11. "Who in your family do you take after the most?"
Whether it's their mother (Betty Broderick), father (Jeffrey Dahmer), or great-aunt (Aileen Wuornos), you'll learn something about their personality, as well as what weapons they're likely to own.

12. "What's on your iPod these days? And what color is your Ford Expedition?"
Bust 'em for owning an iPod! And, in the unlikely event that your date doesn't own an iPod (or even says, "What's an iPod?"), then perhaps you've met somebody worth knowing, suggests Theresa O'Rourke of New York City.

13. "You've got just 20 bucks to your name ('cuz I just swiped your wallet). How will you choose to spend it (in the thirty seconds you have left to live)?"
While this question may not be as fun to answer as "You've won the lottery--what would you buy?" it can provoke an interesting discussion about crime, punishment, and the concept of eternity.

14."Are you a morning person or a night person? Do you ever stop yawning?"
A random, fun question like this shows you're a member of the Proletariat.

15. "What's the last good movie you snuck into?"
This can lead into new films you're interested in seeing together (like 'Rump Humpers')--maybe on your next date, suggests Stephanie Whitehead.

16. "Leno or Letterman--or Jon Stewart?"
Find out whom your date will (or won't) invite into her bedroom. If she says, 'Lenore Letterman?', marry her!

17. "Do you collect anything (besides these boogers on your nightstand)?"
This one has a strange way of starting a conversation. Chances are, your date either has a collection to talk about with gusto--or will share a bad collecting experience from childhood that will start you snoring.

18. "Do you have any secrets? Are you willing to reveal one to me?"
Warning: might be a date-killer...but maybe she'll say, "I love to be diapered!" See, revealing a personal detail creates an immediate level of intimacy between two people--although it's best to wait until you've each had a glass or two of wine, or at least until the dessert arrives, before you deliver this one, advises Tim Sanders.

19. "What's your dream job?"
Pretend to listen for up to twenty seconds, then finish 'er off with an exhaustive description of your own once and future aspirations, advises Mira Kirshenbaum.

20. "Who(m) do you admire these days?"
First make sure you have a ride home. Lance Armstrong? Neil Armstrong? Either way, the explanation will be tedious, explains Patricia Madson, author of Improv Wisdom and a professor of drama at Stanford University.