1. “I love your name; what’s the origin? Were you named after anyone in particular?” Just about everyone’s name has a back-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.
2. “Where did you go on your last trip?” Whether it was an exotic safari or just a weekend in Jersey, people love to talk about the places they’ve traveled, suggests Elizabeth Bates of Boston, Massachusetts. Plus you’ll find out whether they’re more drawn to cities, beaches, or exotic locations—giving you still more conversational fodder.
3. “If you could do college over, what would you study?” Perhaps they would forget economics and take theater, for example. Definitely gets them talking and reveals their innermost wishes.
4. “What’s your favorite new restaurant?” You’ll have an instant window into your date’s likes and dislikes when it comes to cuisine. And if that topic doesn’t pan out, ask about their favorite dishes to cook at home, advises Stephanie Whitehead 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, that tells you something, too.
6. “What trait 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.
7. “What’s your take on ____ (current event)?” Skimming the Op-Ed section of the newspaper before your date keeps you up-to-date, suggest Steven Kim of Philadelphia. Not that you need to engage in serious CNN-style discussions; instead, keep it light and avoid controversial topics (sex, politics, religion), unless you really want to feel like you’re on Crossfire.
8. “How do you know ____(mutual friend)?” Obviously, this one will only work if you have a friend in common—but if you have that in your corner, work it, suggests Tim Sanders, relationship expert and author of The Likeability Factor. You’ll be able to blab about how you each met the pal, what you think of your buddy’s new job, and so on.
9. “What are you reading right now?” Even if it’s a magazine, everyone does a little browsing. Find out about what’s on their bedside table, says Alyssa Citarella, of Norwalk, Connecticut, and you’ll learn something about their literary tastes and hobbies, which is a springboard to other conversations.
10. “Can you believe this ____(heat/cold spell?) It makes me want to move to ____. How about you?” The weather may be a predictable topic, but the way you pose the question doesn’t have to be so. Chances are your date will reveal whether or not he or she has considered relocating to another clime, offers Mia Kirshenbaum.
11.“Who in your family do you take after the most?” Whether it’s their mother, father, or great-aunt Louisa, you’ll learn something about their personality, as well as how close they are to their clan.
12. “What’s on your iPod these days?” Discover their musical tastes. And if your date doesn’t have an iPod by now? “Well, that’s a whole other topic for discussion,” suggests Theresa O’Rourke of New York City.
13. “You’ve got just 20 bucks to your name. How would you choose to spend it?” 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 priorities.
14.“Are you a morning person or a night person?” A random, fun question like this shows you’re not all serious, all the time.
15. “What’s the last good movie you saw?” This can lead into new films you’re interested in seeing together—maybe on your next date, suggests Stephanie Whitehead.
16. “Leno or Letterman—or Jon Stewart?” Most people swear allegiance to one of these nighttime chatters—find out whom your date invites into their bedroom.
17. “Do you collect anything?” 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’ll get you both gabbing.
18. “Do you have any secrets? Are you willing to reveal one to me?” Even if the answer is that she (or he) is wearing red underwear, revealing a personal detail creates an immediate level of intimacy between two people—although it’s best to wait until you’ve both 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?” Then follow up with a short description of your own once and future aspirations, advises Mira Kirshenbaum.
20. “Who do you admire these days?” Lance Armstrong? Neil Armstrong? Either way, the explanation will be very revealing, explains Patricia Madson, author of Improv Wisdom and a professor of drama at Stanford University.
Kari Molvar is a writer in New York City.
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