Great Date-Night Conversation… It’s Yours!

You’ll never face another awkward silence with these four smart talk tactics.

By Caroline Stanley

ure, you’ve exchanged some juicy emails, chatted a few times over the phone, and covered all the basics. Now it’s time to meet up for a (gasp) first date, and the one thing that keeps running through your head is, “What if we have nothing to talk about?” So we asked Dr. Tina Tessina, Ph.D.,
I always ask first dates about their favorite childhood toy.
psychotherapist and author of Gay Relationships: How to Find Them, How to Improve Them, How to Make Them Last to weigh in on some of your first-date conversational tactics.

1. Chat about the closet
In the gay and lesbian community, coming-out stories vary tremendously, yet everyone can identify with them. “On our first date, my boyfriend and I discussed how ‘out’ we were,” says Andy, a student from Wilmington, North Carolina. “We talked about the first person we were out to and when we realized we were gay... these were things that both of us could relate to.”

Why it works: “If you find out you’re in a similar place, you’ll be more relaxed around each other,” says Dr. Tessina. “And if you’re different, you’ll have even more to talk about!”

2. Find out what they love
Whether it’s a beloved pet dachshund, a neurotic best friend or the final episode of Sex and the City, everyone’s got a topic close to the heart that he or she can talk about endlessly. “I always ask first dates about their favorite childhood toy,” says Ben, 33, a lawyer in New York. “Either you bond over having something similar—or you get to tease them about it!” If you’re stumped for something to say, compliment something he or she is wearing. Once your date’s shared an anecdote about the item, make sure to reply with something about yourself and another question: “Oh, you got that in Chinatown? I used to have a favorite dim-sum spot there, but it closed down—do you have a favorite restaurant around there?”

Why it works: Discussing something that makes your date happy will cause him or her to have good feelings during the date—which will later be attributed to being around you, of course. According to Tessina, “Anything that gets your date to talk about personal stuff is good—you learn about their tastes, hobbies, and friends that way.”

3. Take the “out in left field” approach
“Sometimes asking something quirky and provocative, like, ‘If you could start over life again as a man or a woman, which would you choose?’ can be a good ice-breaker,” claims Sarah, 26, from Boston. As long as the topics are silly or out-there enough that they won’t trigger emotional or political
It doesn’t hurt to prepare for certain touchy topics that can come up casually.
debates, “What if…” and “Would you rather…” challenges are fun ways to break up the pattern of first-date chit chat. Check out some sample brain-teasers at

Why it works: Dr. Tessina lauds these questions because they offer an opportunity for a person to reveal something surprising on a first date. It’s also a fast way to find out if your date has a sensibility — and sense of humor — that’s in sync with yours.

4. Know how to handle the tough topics
Now, you don’t want to seem like you’re reading a monologue, but it doesn’t hurt to prepare for certain touchy topics that can come up casually: What you’d like to be doing career-wise in 10 years, how you get along with your parents, and so forth. “I always go into a first meeting dreading the ‘discussion of previous relationships’ portion of the night,” says Rob, 27, from Sarasota, Florida. “I craft a response ahead of time that reveals just enough—without digging myself into a hole.”

Why it works: “It’s important to analyze your prior experiences for yourself and develop something to say about them,” says Dr. Tessina. “But it’s fine to say something simple like, ‘I’m still too close to the experience right now. Let’s save that topic for later.’” And have a positive conversation-continuer on hand (try, “Are you friends with any of your exes?” or, “What’s the weirdest way you’ve ever met one of your boyfriends?”), so that even if you’re deferring the question, your answer doesn’t become a buzz-kill.

Caroline Stanley is a New York-based writer whose work has appeared in CosmoGIRL, Ladies’ Home Journal, and Harper’s Bazaar.
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