How to Break the Ice with Your Seatmate on a Flight

Do you find yourself on flights full of strangers all the time, but never seem to meet anyone new? TPG Contributor Dan Nainan, who's both a world-traveling comedian and a shy introvert, shares his tips for reaching across the divide/armrest and making a valuable connection with the person in the airplane seat beside you.

I think it's a shame when two people sit next to each other on a flight without saying a word to each other. After all, that person could be a potential friend, date, customer, employer — or even your future spouse.

However, despite the fact that I'm an entertainer, I'm essentially an introvert at heart, quick to clam up and become a wallflower in any social situation — including air travel. If you're shy like me, how do you put aside your fear of being the overly chatty seatmate and actually start up that first conversation?

1. Smile and Say "Hi"

I think it's critical to get things off to a good start when you first sit down by employing the simplest of gestures. I haven't yet encountered anyone who won't reciprocate when I smile at them and say hello.

This impulsive act can seem like a tall order for an introvert, but what's the worst that could happen? If your seatmate doesn't acknowledge you, they're someone you wouldn't want to talk to, anyway. If they say hello and then put on their headphones or stick their nose in a book, then hey, at least you tried. It's most likely that your seatmate will be up for a few pleasantries and a short chat, making your flight go more smoothly, but the two of you may really hit it off.

2. "Can You Take My Picture?"

If "hi" feels too intimate, try what I consider to be the ultimate line for breaking the ice with anybody, anywhere, in any situation: "Can you take my picture?" I've never had anybody say no — not once — and I've managed to make some wonderful friends this way. Skip that selfie and get a better souvenir in the bargain.

3. "Going Home?"

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This seemingly innocuous question is a surprisingly great conversation starter, as it really gets people to open up.

For example, on a flight to Houston last year, I sat next to a gentleman who was only on the flight because his private jet was being repaired (no, really!), a fact I only discovered because I asked if he was going home. I told him I was impressed and surprised, he asked me a few questions about myself, and we soon learned that we actually had a ton in common. When we landed, he invited me to dinner with his wife at a fancy sushi place where the bill came to more than $400, and though I tried to pay my share, he absolutely wouldn't let me.

This past weekend, I texted this same gentleman to let him know I'd soon be landing in Houston and would like to meet up if he had some time. He immediately texted me back and invited me to join him at a Mötley Crüe concert at the Toyota Center, where he and some friends had a suite with unlimited food and drinks (too bad I don't drink alcohol). Afterward, a massive party bus picked us up and drove us to a night on the town. None of this would have happened to me if I'd put in my earbuds and tuned out the guy sitting next to me on a random flight to IAH.

4. Shiny Objects and Open-Ended Questions

Strapped for small talk? Try looking at your seatmate's gadget of choice and asking, "Say, isn't that the latest diamond-encrusted iPhone 9S Plus?" People who love their electronics often love talking about their electronics.

Keep in mind, though, that open-ended questions tend to yield more conversation than simple yes/no questions. For instance, "What do you think of the political situation in South Sudan?" might work far better than, "Do you like this airline?" And you never know, you might just learn something interesting about South Sudan.

5. What (Else) Do You Do?

The conversation with your seatmate will more than likely come around to what you do for a living, but consider waiting until you've both been talking about other things for a while. In America, "What do you do?" is a common question early in a conversation between strangers, but in other countries, this isn't the case. For example, a common ice-breaker question in Germany is, "Where are you going on vacation this year?" And just like that, you'll be talking to each other about where you're going next or which places are your must-see destinations.

Keep the Connection Going

If I'm getting along famously with my seatmate and he or she expresses a desire to get on the Internet, I'll offer to share my Wi-Fi connection. What's a little web-browsing between friends? When we land, if my seatmate and I are both connecting to another flight, I'll often ask if they'd like to be my guest in the airport lounge.

If it's time to say goodbye, I'll ask to exchange business cards or contact info with the person and then I'll follow up with an email greeting within two days. I find that if you wait too long to get in touch, the person with whom you had a seemingly special conversation at 30,000 feet might just forget who you are.

If you're up in the air a lot, remember that you have the opportunity to sit next to and connect with some amazing people — and some of those connections can be life-changing. So don't be afraid to invite that person to talk to you, for as Will Rogers once said, "Strangers are just friends I haven't met yet."

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