How to Flirt on an Airplane Ride

I flew to Wisconsin over the weekend for an old friend's wedding ... and got in some good flirting practice on the plane.


Over the weekend, I was in the very pretty city of Madison, WI*--home to the world's largest producers-only farmer's market; to one of the most desirable state colleges in the country; and, also, to my dear friend from college, B.B. (a history professor) and his lovely bridge (a history professor-to-be).

Unfortunately, my trip started out rather inauspiciously.

I rarely fly, partly because I'm irrationally scared of death by airplane crash, and partly because I find the whole thing so stressful--between flight delays and early departures and red-eyes and waiting in long lines and even simply getting to the airport on time, there is so much potential for things to either go wrong or just flat-out suck that I don't always enjoy the process. (When is the U.S. going to get a decent train system, by the way?)

But on Friday morning--despite the fact that I initially took the subway in the wrong direction, away from the airport--I managed to figure out quickly enough so that I didn't arrive at the American Airlines terminal at JFK too terribly late; I still had 45 minutes to go before my flight, which seemed like more than enough time to me. I was even saying to myself, Really, this stuff is not so hard; I really ought to avail of the airport more often.

Now, I'd forgotten to check in online before I left my apartment, so I marched right up to the service counter and pushed my itinerary across the counter to the American Airlines clerk there.

She looked down at it, frowned, and then had what seemed to be a five-hour discussion with a co-worker about whom the co-worker could get to cover for her while she ran an errand. Once that was settled--in what was actually only about five minutes' time--the clerk looked up at me and asked me a very polite question: "You do know you're at the wrong airport, don't you?"

One of the many things that makes living in New York City stressful: the presence of not one, not two, but three possible airports to keep straight.

I dashed out to the street. climbed into a cab and took a very expensive ride over to where I was supposed to be: at New York's LaGuardia. Amazingly, I managed to arrive there with about 7 minutes to go before my flight took off ... and I managed to check in, sign up for a standby flight (just in case), get past security and race to the gate that my flight was leaving from ... to get there exactly on the dot of 12 noon, which was when the plane was supposed to take off.

I watched the doors close before my eyes. I pleaded with the woman at the counter there to let me on, but no dice. She said there was a decent chance I'd make the next flight to Chicago an hour later.

And sure enough, I did make that one. And as long as it landed on time, I'd be able to make my connection to Madison, no problem.** Woo-hoo!

As we got ready to depart for the Windy City, I'd already settled into my aisle seat when an attractive red-haired dude stopped by my side and pointed to the window beyond. "Excuse me," he said. He was wearing bright red sneakers with a shirt with blue, red and yellow lines in a neat, cheerful pattern, as well as a pair of smart rectangular glasses with a thick black frame, and carrying a red and grey Freitag messenger bag. In other words, he was quite cute, in his quirky way.

But beyond smiling and thanking me when I stood up, he didn't seem to take much notice of me. Shoot! I thought.

At the same time, there was something open and friendly about him; and when he got up, shortly after the pilot turned off the fasten-seatbelts sign, to use the restroom, he left the thick book he was reading on the seat between us, which I interpreted as something of an invitation. Eyesight Alone: Clement Greenberg's Modernism and the Bureaucratization of the Senses, it was called. As it so happens, I've read an essay or two by this Greenberg fellow--who was probably the most influential critic writing during the heyday of Abstract Expressionism (as well as one of the first to praise Jackson Pollock). What's more, I love modern art.

So when the cute red-head came back from the loo, I took a chance and said to him, "You must be getting a Ph.D. in Art History, huh, if you're reading that book?"

Indeed, he was getting his doctorate in Art History. So I plied him with questions: What was his thesis on? What was the book about? And how had he decided to get a Ph.D.?

We fell deep into an intriguing and pleasant conversation, during which I noticed one more appealing thing about him: an attractive gap between his two front teeth.

I had a hunch that Dr. O. Art might not be straight, however, and as we continued to chat, I found out he was, indeed, gay. That led to an even more interesting discussion, as he told me about his strict religious upbringing, and his early attempts (encouraged by the members of his church) to re-program himself so that he would eventually be attracted to women. It wasn't till his first year in college--when he found his way to a community of gay men, for the first time in his life--that he finally began to come to peace with his sexual orientation. Regardless, although he's in his late thirties now, he's had a hard time finding a relationship ... and sometimes, he worries that he'll be alone forever.

"Believe it or not, I totally relate," I told him.

Anyway. Yes, the guy I ended up flirting with was a gay man, but I was quite glad to make his acquaintance, and to have such a wonderful conversational partner, who made the time, um, fly ...



Since we're not always lucky enough to be seated next to a charming stranger on the plane itself, choose your seat in the boarding area strategically. Look around for someone who seems appealing--and seems to be alone (without any finger jewelry). Then take a seat diagonally across from the person, or a seat or two away on the same side.


To increase your chances of a having a "serendipitous" flirtation with someone, pack a book--or maybe a few, and make sure the cutie you've seated yourself next to has a chance to see the cover; that might just be all he or she needs to start a spontaneous conversation with you, the way I did with Dr. O. Art. I think a non-fiction book is your best bet, since it's usually fairly easy for anybody to get a handle on what the book's about just by reading the sub-title (the way I did). Try one of Malcolm Gladwell's bestsellers, for instance--either The Tipping Point, Blink, or his latest, Outliers--would probably serve you well. After all, lots of people have at least heard of him (if they haven't read his books or his New Yorker articles); lots of people find his writing really interesting and applicable to their lives; and while he gets credit with the smarty-pants crowd, he also has such an accessible style that you don't have to be a brainiac to enjoy his books.


Of course, no matter how interesting your reading material, the Attractive Stranger you sit next to might not be bold enough to strike up a conversation with you. So you'll have to take a little more initiative. Don't worry; it should be easy. Simply say something like, "Hey, I have a question for you." Then explain, in a sentence or two, the hypothesis of the book you're reading. (You don't even have to have read the book to do this; you can probably find the main thrust of the book summarized on the cover jacket, or the back.) Then ask The Attractive Stranger what he or she thinks about the hypothesis. (Or, simply summarize the article you've been reading in a magazine, and ask The Attractive Stranger what he or she thinks about that.)


The beauty of the airport flirtation: There's only about an hour before you board ... so if the conversation goes terribly, or falls flat, you won't have long to wait before you can escape. (You can also excuse yourself at any point by saying you'd like to use the bathroom or buy a snack.) Similarly, if you start chatting in-flight, the whole thing will be over once you land. (If you're going somewhere far, far away--like South Africa or Australia--you might want to wait until T-60 minutes before engaging with someone sitting next to you, just in case.)


So what have you got to lose? Go for it! Chat up that hottie!

Anyway, I did arrive in Chicago just in time to make my original connection to Madison. I'll tell you more about the weekend tomorrow!

But what about you guys? Have YOU ever flirted with a stranger in the airport or on a flight? Do you have some insights for us?




Sounds like our fathers are peas in a pod: The grocery store is also my dad's favorite place to flirt.

AND MADGE: A cool helmet, huh? The trend here in NYC seems to be that bikers are waiting skateboard helmets--which do look cooler: they fit closer to the head, are a bit smaller and less shiny. The drawback, I hear, is that they get much hotter than bike helmets; I also wonder if they are as safe (since skateboarders can never go quite as fast as bikers--and the faster you go, the greater the potential impact). Here's another idea: Call the people over at Ride Brooklyn, and ask them for their thoughts.


A few notes on Madison, in case you are planning to go:

-There's a gorgeous park on Lake Mendota, one of the finger lakes.

-I stayed at the exceptionally lovely Madison Concourse Hotel. The service was impeccable--and so were the pillows!

-The bagels at a place called Gotham were surprisingly delicious--which is high praise, coming from a New York bagel snob like myself.

-The favorite local bar, as far as we could tell, seemed to be Genna's.

**I can't tell you how nice American Airlines was about accommodating me, after I made such a stupid mistake!