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The best $1,419 I ever spent: Flights for my long-distance relationship

I flew on a plane for Ana 19 times before we finally lived in the same place. It was totally worth it.

Ana and I were in Columbus, Ohio, for a friend’s wedding, our first big celebration as a couple. An apartment full of friends hurried to get ready before the night of heartfelt vows, joyful dancing, and talking really loudly over music. I still remember dancing so full-spiritedly to Despacito (it was 2017) with Ana at the end of the night and leaving the party on a high.

Going to sleep only a couple of hours later, Ana and I held each other in sadness.

The next morning, I squeezed into the back seat of a car to head back to New York City with friends. Tears rolled down my face as the car pulled away from Columbus, from Ana, from new love, looking back at her standing alone on an empty street.

She was off to Evanston, Illinois, to start her master’s program at Northwestern, and we were looking at about two years of dating long distance. We had only been seeing each other for six months, but Ana was worth it.

In our mid-20s and not really sure what we were looking for from dating, we met in an obvious place: Tinder. Our first date was at a now-closed Upper West Side bar. Ana told me months later she didn’t like the place, but luckily our conversation and chemistry overcame the unpleasant aura of an empty bar on a Tuesday night. On our second date, we kissed in the dark as an art film surrounded us at the Guggenheim Museum. Everything seemed so easy, so lovely, even on those early dates.

Soon, Ana was inviting me to her large friend gatherings, parties, and even a family trip to Rehoboth Beach. Being with her, and being a part of her life, was more seamless than anything that had ever happened to me. More welcoming and more loving. I’m not someone who really likes going to events, meeting new people, being in unfamiliar situations, but that six-month period was the best version of new and unfamiliar for me.

That’s why any reservations about continuing our relationship once Ana moved to Illinois were slight in comparison to our potential together. That potential was also what made it so hard to cope with the distance.

The tears and sinking feeling of missing Ana that hit me in Columbus became all too familiar. Eventually, so did the absolute dread of being in O’Hare Airport (I’m from Queens, so I found LaGuardia Airport’s dreadfulness slightly charming). I honestly didn’t think I’d be able to keep a long-distance relationship going — my primary love language is touch, as corny as that sounds. In simply being close to Ana, I felt the deep, essential warmth of the connection we had.

That last night in Columbus, we worried about what our relationship would be during weeks-long stretches without holding each other, talking to each other over weekend scrambled eggs and toast, and Ana’s loving, caring responses to my incoherent grunts and ramblings.

Before we’d even geographically parted ways, I booked my first flight to visit Ana in Evanston. Planning a visit before we set off in different directions made us feel a little more secure about the beginning of being apart. Long-distance dating also required far more logistics planning and money discussions than a typical six-month relationship would. We talked about whether we could manage the cost of the flights — luckily, the answer was yes. It did, however, involve rounds of “are you sure,” “I think so,” “well, let’s open Google Flights and check out the prices.”

In Ana’s words, I’m “extremely type A” to her “regular type A.” I was always determined to find the best weekday flights for my more flexible travel schedule — one time I flew roundtrip for less than $100 — and Ana had to take the hit of Friday-Sunday travel and shell out $300 to American Airlines every so often.

We hadn’t thought much about what would happen afterward. We didn’t know if we’d move in together if she came back to New York or live separately for a while as we continued dating. If she got a job outside of New York, I didn’t know if I’d be willing to uproot and move elsewhere. When I talked to people before Ana’s move, I shrugged and sighed. “We’ll see what happens,” I said with the resignation of a mid-20s introverted pessimist working through years of depression, simply stumbling through an alienating world. Still, those first six months with Ana helped me steady myself against the aimless floundering.

In my apartment in Sunnyside, Queens, I’d lie awake late after one of our FaceTime calls, scrolling and scrolling and scrolling on Twitter, trying not to disturb my roommate while I retrieved a midnight snack, feeling lonely, and waiting for my stress to relent enough for me to sleep. In Evanston with Ana, we’d hold each other, falling asleep at a time well before the 1 or 2 am I’d be restless till at home.

The more time we spent together during a visit, the harder it was to part ways, the sadder we were, the more likely it was that I’d be trying to hold back tears in my Basic Economy middle seat. Still, we dealt with the cost, the logistics, and all of the air travel mishegoss for each other.

My very last flight to Chicago was bittersweet, and the sweetness came from more than the fact that I booked the flight with American Airlines miles. I’d come to enjoy the respites from New York and my visits to Unicorn Cafe in Evanston. We still didn’t know where Ana would get her first job; we wondered if it would be long distance all over again. At that point, though, we knew we could do it. I wasn’t fully redeemed from my general pessimistic posture, but I was able to be more hopeful about things. Ana graduated, I bid the Unicorn Cafe and Lake Michigan farewell, and I welcomed the next stage of our relationship.

Then, a few weeks after I flew back to Queens from Chicago for the last time, Ana moved to Philadelphia for her first post-grad job. I so hoped she would move back to New York; alas, we would be living in different cities again. Instead of LaGuardia to O’Hare on a plane, though, I’d go from Port Authority to 30th Street Station on a Bolt Bus. Some would even debate whether New York to Philly could be considered long distance.

Well, now there’s no need to debate.

In March 2020, Ana and I went from not living in the same city for roughly 2.5 years to suddenly hunkering down together during the pandemic in Philly. I took a bus down to see her on March 9, just before the national awakening to the severity of Covid-19, and was not eager to board a Bolt Bus a few days later as the virus surged. With the geographical distance now clocking in at zero miles, neither of us knew how our relationship would weather such an intense, sudden change. Was there going to be too much closeness? We had gotten through months without seeing each other, but could we get through a month (or two or three) of seeing each other all the time?

Those worries faded quickly. Cooking meals together, having the same bedtime, analyzing Tiger King, rescuing our little pup Luna, doling out and fulfilling cleaning chores, it was all pretty seamless. (Luna is a handful but her love language is touch too, so it works out.)

Living with Ana reinforced how much we belonged together, and, really, that too much closeness or touch wasn’t a thing for us. I would take 19, 29, 39 more flights to keep us going — luckily, I don’t think that will be necessary.

Arthur Tarley is a writer, activist, and union member from Queens.

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