Turn a date from awkward to awesome

How to loosen up an uptight date

By Laura Gilbert

You two had great online rapport, and your phone calls were filled with witty banter. But now that this hot prospect is sitting face-to-face with you on a date, it’s painfully obvious that nervousness has this person in a vice grip. Your potentially wonderful evening has turned into an uncomfortable mix of halting small talk and awkward silences.

You’ve got two choices at this point: A) push your peas around on your plate and try not to be caught checking your watch, or, B) use some smart measures to crack through your date’s defenses and help him or her relax so you can, too. Let’s take a closer look at option B to help your anxious date chill out a bit.

Acknowledge the elephant in the room
When there’s tension in the air, sometimes the best thing to do is acknowledge it. “If you’re bold, say something like, ‘First dates are always so uncomfortable — wanna pretend it’s our second?’” says Nancy Slotnick, author of Turn Your Cablight On: Get Your Dream Man in 6 Months or Less. The idea here is to use a little humor to let your date know you understand how rough initial get-togethers can be — and that you have an easygoing attitude about it. Slotnick also recalls a man who broke first-date tension by asking, “On an awkwardness scale from one to 10, how would you rate this moment?” “It’s one of the best lines a guy ever used on me when I was single,” she says. “It put us both at ease.”

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Look like you’re listening
Nervousness often melts away when someone’s certain the other person is genuinely interested romantically. And while you could swear you’ve been nothing but attentive as your date recounted his or her first attempt at surfing in Costa Rica, your expression might show otherwise. “A lot of people, without realizing it, offer very little facial feedback,” says Susan RoAne, author of What Do I Say Next? and RoAne’s Rules: How to Make the Right Impression. In other words, listening is not enough; you must also look like you’re listening — something many of us forget because it’s not necessary in web-based and phone communications. To do this, be sure to make eye contact, smile, and egg your date on with interjections in the conversation, such as “how interesting!” or “I’ve never heard that before.” It may feel forced at first, but the results will be so immediate and effective that you’ll probably soon find that conversation really picks up.

Shine the spotlight on yourself
When dates act tense, it’s usually because they’re worried about the impression they’re making. “People get really preoccupied with themselves, and the best way to get them to loosen up is to put all the attention on you,” says Laurie Puhn, J.D., author of Instant Persuasion: How to Change Your Words to Change Your Life. “Talk about your day, the place where your date is happening, or something a friend did.” As long as you seem to be having fun, your date will feel the pressure to entertain you lifting. “Eventually the person will calm down and you can shift the focus back onto him or her,” says Puhn.

Share a mortifying confession
Remember that moment you tripped dramatically walking into a party or made a Freudian slip in front of your boss? Finally, some good can come out of your past humiliations if you’re willing to share this personal tidbit with your date. “In awkward moments, what seems to work is telling an embarrassing story. It lightens the mood and relaxes the whole situation,” says Javier Alba, a manager at Las Vegas nightspot Tabu Ultra Lounge who’s seen more than his share of uptight dates turned around by a smooth talker. Not only will your confession get you both laughing and demonstrate your (admirable) ability to laugh at yourself, it will also show that you’re not perfect, which can soothe a date who’s intimidated around you. One caveat: Stay away from upsetting stories or relationship snafus, which can send a completely different message to a nervous date.

Ask your date for advice
Everyone loves being helpful, so draw out a shy date by soliciting his or her opinion. “Say something that shows your vulnerability, like ‘Can you help me figure out what’s good on this menu? I tend to order the wrong thing,’ or ‘I always get nervous meeting with my boss because he’s so critical. Any advice?’” recommends Slotnick. Another tip is to ask your date what he or she thinks about one of your friend’s dilemmas. It’s a low-pressure way to get the person talking — and feeling like you value his or her take on things.

Throw in some curveball questions
If anyone knows what it’s like to make conversation with someone who holds his or her cards close to the vest, it’s Eric Alt, a Los Angeles-based celebrity interviewer. His advice? Break the tension by asking something unexpected. “Throwing curveballs is one of the best ways to get someone who’s being reticent to open up,” he says. Off-the-wall hypothetical situations are a good starting point. Ask, “What food would you eat if you had to eat the same thing at every meal for a month?” or “What invention do you wish already existed?” It’ll jar your date out of the cerebral “Am I doing OK?” date-night worries and get both of you engaged in the moment — and each other.

New York City freelance writer Laura Gilbert has written for Health, Stuff, Maxim, The Knot, and other publications.

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