Bad Date Ideas in Boston

I met Amy on the subway from Boston’s Logan Airport. I struck up a conversation with her son (6 years old?) and asked him to guess what was in my friend’s bike box (hint: a bike). He guessed rollerskates.

Have you had times in life where you feel yourself glow? For me, it has been a place of generosity, humor, and a sense that I can do no wrong. I’m more patient, kinder. It’s like Csikszentmihalyi’s flow, but not activity-dependent. This time it had something to do with coming back from a week skiing in Utah, recharging the batteries that had drained as a graduate student at MIT. My glow caught Amy’s attention and she agreed to go on a date.

I grew up in rural Alaska and never felt at ease in Boston. I was struggling through a Ph.D. program, starved for recreation and companionship. I gave up on recreation because driving my 1981 Chevy S-10 in and out of Boston was stressful. The best feature of the Chevy S-10 was an after-market wooden steering wheel I inherited from an ex-girlfriend. The rest of the truck was crap: A finicky idle, plexiglass passenger window, and squishy brakes.

I drove the truck to the hospital for foot surgery and a college buddy drove me home. I warned him that the brakes were squishy and that he needed to anticipate his stops. He blew through a stop sign leaving the hospital and I was like, dude, Alex, you have to anticipate the stops. He replied that the brakes were really bad, and that the truck was unsafe to drive. I was like, duh.

I was on crutches for a few weeks, but when I could drive again, I discovered that the brakes weren’t just squishy, they were gone. The brake line had broken free. Sorry Alex! I installed a new brake line but then I caught the truck on fire troubleshooting the idle, so it was kind of a moot point.

My safe place in Boston was the Arnold Arboretum—a precious pocket of the natural world. This is where I proposed to meet Amy for our date.

My officemate at MIT, Brian, was almost as excited about the date as I was. He cheered me on and provided passive guidance through questions: Are you going to shave? And wear a different shirt? How are you going to get there? He was unimpressed with my plan to pedal the BMX bike that I bought from a high school football player.

I had planned to go straight to the arboretum from campus, but I followed Brian’s advice, raced home, shaved, and changed shirts. I was too late to catch the T, so I hopped on the BMX.

I rolled up to the arboretum and the first thing Amy said was, “My son wants a bike like that.” I was like, yeah, these are sweet bikes. I showed her my only trick (hopping up and down on the rear tire while standing on the pegs) and gave her a short ride standing on the pegs, which were an awkward fit for her shoes.

We entered the arboretum as daylight turned to dusk. We made small talk but it was obvious that Amy was uncomfortable. At one point she said, “My girlfriends would be so worried if they knew I was out here.” And I was like, “Because of those heeled shoes?” And she was like, “Uh, no. Because I don’t know you and you could murder me and hide my body. Haha.”

I teach rescue training in Alaska, and a constant theme is the need to get better at situational awareness. Well, I failed that task with Amy and I felt terrible. I wish this was just an Alaskan-kid-in-the-big-city thing, but it was more of a men-are-clueless-about-women’s-experiences thing. And that sucks. I stopped in my tracks and showed her the contents of my backpack: snacks and a flashlight. Because that’s what an Alaskan kid brings on a walk in the woods.

We quickly pivoted to a pizza pub where the lighting and other customers helped Amy feel safe. I did a poor job of coming up with relatable conversation topics. After dinner, she put my BMX in her car trunk (so practical!) and gave me a ride home. I thought it was a disaster of a date, so I was shocked that she wanted to make out.

Brian was pacing circles at the office in the morning, waiting for my report.

How could you give me all of that advice and not mention that it was totally unacceptable to take a date on a walk in the woods in Boston?

Oh. Yeah, that was a terrible idea. The arboretum at night was so far outside the range of possibilities that it didn’t even register. So … no second date?

There was a second date. It was the evening after my foot surgery and I had just survived a drive home through Boston in a truck without brakes and was loopy on half of a painkiller. I don’t remember much from the date.

I soon discovered that golf courses (closed for the winter) were a better walk-in-the-woods-date destination. After a walk through the Woods Hole Golf Club, my date said, “I love that we just got lost on a golf course. I didn’t even know that was possible.” And that made me glow.