Anything You Ask

Hour 19

“So, do you have a special lady friend?”

His question was a surprise. I hadn't had many personal conversations with my flight instructor. Gary was an older guy, crotchety, always wearing an old baseball cap over a thin ring of white hair, and occasionally prone to complaining about “women drivers” when he'd see an aircraft having trouble following the taxi line. We were sitting in the cockpit of one of the flight school's aircraft as I prepared to start the engine for the day's lesson.

I looked up from my checklist. “Uh, yeah,” I replied, a little cautiously.

“Oh,” he said, with a hint of disappointment. “Well, I've gone out on quite a few dates up there,” he said, motioning to the sky with his eyes. I had to hide a smile. If you met Gary on the street, your first thought might be that he enjoyed sitting in a rocking chair yelling at kids to get off his lawn. But Gary the Lothario? That was unexpected!

“Let me tell you something,” he continued. “If you take a woman up there on a first date, one of two things will happen. Either she'll run away screaming and never want to see you again,” he paused, looking at me.  “Or she'll do anything you ask.”

I laughed. I had no idea if he was serious. I went back to the checklist.


Hour 449

The next few years brought many changes: after graduating, I moved to Seattle, and my girlfriend D. and I eventually decided to part ways. When I started dating again, I remembered Gary's advice and -- okay, I'll admit it -- I was curious to see if it was true.

Soon after this, I found myself browsing an online dating web site, and tried using “flying” as a keyword. And there she was: well-read, fun-loving, in a professional career, ridiculously sexy, and with experience both flying and skydiving. What more could I ask?

“That one is not going to write back to you, dude,” my friend Dave told me when I sent her profile to him. “Write to her, but don't get your hopes up.”

“But I have an in!” I countered. “There's a picture of her with her arm draped over the propeller of a Cessna, and I recognize the airport from the pavement marking she's standing near. That's gotta count for something.”

“Eh, try it,” he said, doubtfully. “But she's ... well ... out of your league.”

My sister, a veteran of online dating, was also skeptical. “Bro, I love you, but a woman like that gets like a thousand messages a day. You have to set your expectations a little more realistically.”

“But her handle is I_Love_Nerdy_Men!  That's me!”

I wrote to her anyway: “Hey, that's Friday Harbor Airport, isn't it?  What do you fly?” A few days later, we were eating sushi and chatting like old friends. I suggested an aerial sightseeing tour for our second date and she eagerly agreed.

“Okay, here's what you do,” Dave said. “Make sure you have plenty of DVDs. When the date is ending, ask if she wants to come back to your place to watch a movie. It sounds better than just asking if she wants to come up to your place for a drink.” Dave is a dating ninja so I decided to give his strategy a try.

The following week we went out for dinner, then drove to the airport together. I pre-flighted the plane and got serious for a few minutes as I did the passenger briefing. We launched into the calm summer evening air and lazily circled over the downtown Seattle skyline without a care in the world. As the sun set over the Olympic mountains, the cockpit was filled with a warm orange glow, and L. was all smiles as she took the controls for a few minutes before I brought us back to Earth.

I was nervous as I put the plane away. Our date seemed to be going well, but I was afraid to ask her to come back to my place. I practiced silently in my head as I attached the tie-down ropes.

Just ask her if she wants to watch a movie or something.  Hey, want to watch a movie?  I have some movies. Want to watch one? Do you like movies? I have some movies. Just act natural. Act natural...

With the plane secured, I walked back to where she was waiting for me on the ramp, when--

“Hey, you wanna go back to your place and watch a movie?” she asked breezily as my mouth hung open, the same question sitting in it, half-formed. The fish had jumped right into the boat.

Oh, Gary. You old devil.

Spoiler alert: we got married almost exactly two years later!

Wedding rehearsal dinner, July 2008