By Amy Keyishian

So you know what your date does for a living, where he or she grew up, and even exchanged some lively dialogue about a recent bestseller you both read. And yet, so far your conversation contains not even an iota of a spark. Does this mean you should write this one off? Not necessarily. First-date and early relationship-stage conversations can often feel like a dry exchange of information, but the good news is there are plenty of ways to get beyond that. Here’s how to talk to your date so you’ll truly connect. 1. Get past the facts
Okay, so you’ve established that your date is a lawyer. Don’t just ask, “Really, for what firm? Do you know so-and-so?” Instead, ask your date how he or she feels about his or her profession with questions like, “Why’d you choose that career? What do you love about it? Is there anything you dislike?” By asking about someone’s likes, dislikes, and motivations, you’re getting to know what makes that person tick. “If someone says ‘I traveled to Italy,’ the standard answer is ‘Oh, I’ve never been there,’ or ‘Oh, Florence is nice,’” says Laurie Puhn, J.D., author of Instant Persuasion: How to Change your Words to Change your Life ( “A better answer is, ‘Really? What did you like most about it?’ Get your date talking about the emotions behind the facts, and you’re well on your way to breaking through to a real connection.” Same goes for you when you’re describing your job or hobbies — describe how you feel about the subject at hand and you’re sharing your life in a whole new way.

2. Meander into hypothetical territory
Truth be told, most people’s daily lives aren’t rife with excitement, so dwelling on reality doesn’t always make for the most scintillating conversation. It may behoove you to venture into “What if…?” territory with comments, like “I sometimes wonder what I’d do with my life if I won the lottery. What do you think you would do?” or “If you had to find a new profession, what would it be?” Conversation like this gets at someone’s dreams and desires, and even if these things will never come to pass, you’ll get to know what makes your date tick. “You can make it a game,” says Puhn. “Pick a group of people nearby and ask, ‘What do you think is going on with them?’ Are they friends from work? Reuniting sorority sisters? The makings of a new five-girl pop band?” As you bounce the possibilities off each other, you’ll get some playful banter rolling in no time, which will help connect you two.

3. Choose good conversational stomping grounds
Of course, if you put yourself in surroundings where there’s more to talk about, all these talking tips become that much easier. “Why do people go out to eat on dates?” asks David Wygant, author of Always Talk to Strangers: Three Simple Steps to Finding the Love of Your Life. “It’s the worst idea. All you do is watch each other chew.” Instead, go bowling. Hit a museum. Browse in a used book or record store. Basically, small talk happens in restaurants. Chemistry talk often involves a more creative location. “The more inventive you are with location,” Wygant adds, “the easier it is to get deep with someone who might be a little less socially adept.”

4. Don’t go on about past relationships
While it’s tempting to think that a foray into comparing former flames will get you two bonding fast, it’s generally not a good idea early on. For starters, you’re bound to let slip something negative or disparaging, which may paint you as bitter or, worse yet, hung up on your ex. Secondly, some people will view conversations along these lines as prying, which will make them uncomfortable and tempted to clam up. The best thing you should say about past relationships is this: “It didn’t work out, but I’m glad since it’s allowed me to meet a bunch of other great people.” The subtle compliment you’re implying will make your date warm up in no time and shift the conversation back to what you should really focus on: each other.

5. Don’t feel compelled to fill the silence
Of course, there are bound to be lulls, no matter how successful your date conversations are. If you realize that’s OK, you might actually make even more of a connection. “Men, especially, tend to be comfortable with silence,” says Dr. Helen Fisher, author of Why We Love. “I find that if I stop trying to draw out the most reticent man and just sit through the silence — by God, he becomes downright chatty.” Conversations have a beat, just like music, and if you tune into someone else’s tempo and let him or her set the pace, you’ll be perceived as a truly sensitive soul. And that might be worth more than the cleverest quips.

Amy Keyishian is a New York City-based writer who’s written for Cosmopolitan and other publications.

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