Getting the Conversation Started: How to Relax & Open Up on Dates

So you’ve spent the past days or weeks texting, emailing (yes, people still do this!), and talking to a match. Now you’re finally meeting face to face, in the flesh. But then it strikes you: this person is essentially a stranger, a stranger with whom you have just agreed to spend time with for a drink, meal, or outing.

Yes, you’ve been chatting online and on the phone, getting to know each other. But that’s not the same as meeting in person where you can gauge whether or not you have any chemistry with one another. In real life, your match is still very much a variable — an unknown.

So, when you meet for the first time, how do you get past that initial awkwardness? You know, the limbo where you feel compelled to be friendly and affectionate because this is “a date,” but know acting too familiar could make you come off creepy and weird.

As a matchmaker who utilizes a combination of matchmaking databases, online dating, and the latest scientific studies in the world of romance and dating to help my clients find love, the first-meeting-chilliness is a problem I’ve had to coach my clients through regularly. There’s just no getting around the fact that when you meet your online match in person for the first time, they’re not much more familiar to you than someone you met that night simply because an in-person meeting is multidimensional.

You can see your date’s facial expressions and body language, hear the intonation in their voice more clearly, even smell them (which, hopefully, doesn’t offend you). It’s a lot to take in and can all be overwhelming. Fortunately, I have a few strategies to help you break the ice on a first date, putting both of you at ease.

Make use of small talk.

Ugh, yeah, I know. Small talk can be the worst. You want to get right into the meaty, exciting conversations and back to the witty banter you’ve exchanged over text. But that’s like going to the gym and instantly doing high-intensity-interval-training without doing some warmups first. You’re going to wind up pulling a muscle — or making your date feel uncomfortable.

So why should you waste your first impression with a new match by talking about what you perceive as nonsense? Like warmups for exercise, small talk gets your body, which is in a state of rest, into a state of activity. Then, once you spend some time talking about how your day has been or what the traffic was like on the way to the restaurant, the hope is you and your date will feel acquainted enough to begin engaging in conversations that are a little more personal.

Ask plenty of questions.

Once you run out of introductions and small talk and your blood is pumping, ready for the main workout, it’s time to get to know your date. And what better way is there to do that than to ask him or her questions?

People generally love to talk about themselves, and they will love talking to you more when you listen to them talk about themselves. So your questions will serve a dual purpose: you get to know your date, and your date gets to enjoy your company.

Talk about yourself, too.

I advise my clients to prepare for a first date the way they would an interview. If you think about it, a first date serves as an interview for the position of “boyfriend” or “girlfriend.” Just as you are on this date to get to know your match, your match wants to have the chance to get to know you. Use the information your date tells you about himself or herself to put your best foot forward and start conversations you both could enjoy.

As you listen to your match, discuss their interests, finding some common ground for relatability. Suppose you both like to hike. Talk about your favorite hiking trails or where you would like one day like to visit. Now you have bonded over a specific area of interest, helping you feel that much more familiar with each other.

One caveat: you may want to think about excluding some topics from your conversations. Those include money, politics, religion, exes, and dysfunctional family dynamics. There will be plenty of time for those talks later, hopefully over cocktails or wine if things work out. Remember, if you do touch on these subjects, there’s never an excuse for treating others with disrespect.

Don’t just tell stories, be a storyteller.

I believe that individual life experiences make us unique while making us relatable to others. As you listen to chapters and anecdotes from someone else’s life story, you get to know who they are in a fundamental sense, particularly what they value. This information helps you form a meaningful understanding of that person.

It’s why I advise clients to keep a selection of stories to share at the forefront of their minds. No, I’m not referring to the one about your divorce (save that for the tenth date, at least!). Instead, talk about the time you went to Las Vegas and met some crazy person on the strip at 3 a.m. How did you react? The funnier, the better.

I don’t expect you to create a list of canned stories to tell in your mind. Instead, as you have a conversation with your date about, say, when your steak will be ready, let the random memory of that delicious steak you once had come to mind, and tell a story around it. You’d be surprised how the most insignificant memory can spur a laugh and bonding moment.

Final thoughts.

Even if you start your date feeling nervous, as you go through your itinerary (I say itinerary rather than script because, in my mind, itineraries leave more room for flexibility), a relaxed feeling will naturally come over you. If it doesn’t, you should, of course, trust your gut. The truth is most people you meet will not be for you or you for them. But that doesn’t mean you can’t have an enjoyable time together.

The skill of being a good first date is not too different from that of being a good dinner host. The ability to break the ice and be friendly and warm using small talk, a healthy back and forth, and telling stories will help bridge the gap between those who arrive as strangers at the start of the night and leave as friends by the end of it. As we all know, it’s often how the best relationships begin.

Reprinted by Permission from Innovative-Match, a full-service relationship coaching firm. (www.innovative-match.com)

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