The pair of Vans with skulls on them that my boyfriend asked about in his first OK Cupid message
The shoes that started my relationship


“Are those Vans with skulls in that photo?”

That was the message on OK Cupid that started my current relationship of almost two-years. Yes, they were Vans, I answered. (Really they were some fancy designer brand trying to look like Vans, but that was too complicated and I didn’t want to get into my spending habits).

“Hey, I think I’m going to get some for myself,” was the next message a few minutes later. The next day my new friend sent me a photo of some custom sneakers with skulls he’d put together on the Vans website. But he wasn’t sure about his color choices.

At First, This Did Not Seem Promising

Over the next week I discovered he lived near the water in a cute little town about a half hour away. He got up early before work to run or ride his bike as the sun rose. He’d send me pictures of the sunrises, shades of pink sliding into orange above dark hills. They were usually accompanied by an upbeat message about having a great day.

Which was a balm. Even though I didn’t do upbeat. I wasn’t sleeping much at the time and everything looked gray. I wondered, with all the early morning communication, maybe he couldn’t sleep much either.

A few weeks before my then boyfriend of eight months said he was leaving me while were at his friend’s house in Germany at the start of what was supposed to be a vacation together. I had to get home on my own with an injured leg. I wrote about that here. I’d been in fight or fight mode since I’d returned, but I’d gotten back on OK Cupid. Despite not being able to spot a sociopath and having dated the abusive guy and the polyamorous mansplainer.

I was bruised. And pretty sure I was cursed. Mom dead at ten. Husband dead at fifty. Middle-aged men pretty irredeemable.

I wondered if I could settle for a friend with benefits kind of situation. I certainly wasn’t finding anything better. But I wanted love. The kind of love that helps you paint your walls and uproot your dead plants and stays around when you’re sick or have your period. (Why are so many older men so squeamish about menstruation? It’s not like they never got married or had daughters or had to deal with their own fluids).

My new friend’s profile did not look promising. Sure, he was tall, tan and trim with a cap of white hair, but he was into tennis and skiing, both snow and water. I don’t do that. His picture showed him shirtless on a ski boat. Not my type, both shirtless and ski boat. He ended his profile with, “May you find friends, lovers and more.” Which I took to mean he hoped most women would look elsewhere.

“I’m not as athletic as you,” I texted when we first started communicating. “I don’t think we have much in common.” But he also sent me a picture of his place, telling me about the new furniture he was getting. And a photo of another pair of skull Vans he’d bought. So we were both into shoes and design. At best, that was probably the stuff of a couple lunch dates.

On vacation together in Carmel last year. Actually happy.

I Didn’t Think What I Wanted Existed in the Modern World

We met for coffee a week after we started texting. He’d come from work, and in his sports coat and leather slip-ons he looked too grown up for me.

“Look I’m really sad,” I told him. “My ex dumped me in Europe. And I think dating is pointless and time-consuming.” So much for best foot forward.

“I’m really sorry about your husband,” he said. “And your mom. I’ve been reading your blog.”

What? Nobody I’ve dated ever bothered to read my blog. He then told me about his own mom dying just six months earlier. He was still grieving. An hour and a half later we parted, having decided we would try to cheer each other up during these times.

Two weeks and more upbeat texts later, I got a call the Sunday night before Memorial Day. “I’m going to take my old convertible on a drive to Stinson beach with stops at my favorite restaurants along the way. Have you ever had breakfast at Fred’s in Sausalito or been to Spinnaker’s?” No and no.

“Don’t feel bad if you don’t want to go. I’m going to go anyway,” he added. By now I knew he did lots of things alone, from eating at restaurant bars with water views, to taking his little ski boat out for drives, to going for overnights to Carmel by himself. He clearly had a capacity for being on his own that I lacked.

He planned on leaving around 8:30 the next morning. “Could I meet you at your place more like nine-thirty?” I asked. But he said he’d pick me up, which would mean an extra hour of driving for him, but he didn’t mind. I’d been missing chivalry. It seemed to have died many years ago.

He picked me up wearing white jeans and a blue t-shirt and I realized, he was gorgeous. I hadn’t caught that before. Months later, he would tell me he was very careful not to look at my legs since I was wearing shorts.

When he wasn’t sure about a street, I offered to navigate on my phone. He accepted gratefully, also a surprise. Most men needed to look like they knew where they were going, as if having a woman direct them from a Maps App was an admission of erectile disfunction. Our date lasted twelve hours, with two meals, a champagne stop, and a bad country band. More on this to come.

Do Not Settle for Something You Don’t Want

There are good people out there. Even if they’re temporarily available only on Zoom. There is no upside to these times, but we are forced to slow down and that gives us time to think about what we really want.

I could have saved myself a lot of agony (and idiocy) if I’d been okay with saying I wanted love in a committed relationship. Someone to wash my patio furniture. Someone with traditional manners instead of acting like we’re both bros. But that would have been uncool.

Yet, once I got that, I realized how little I’d been settling for. Mark Manson came up with the Law of “Fuck Yes or No” which states that “when you want to get involved with someone new, in whatever capacity, they must inspire you to say “fuck yes” in order to proceed. I’d been saying “whatever” but proceeding anyway. So, don’t give up hope. I found my partner when I was 55 and at one of my lowest points since my husband died.

I’ve gotten lovely stories from widowed folks (and divorced ones) who’ve found love at middle-age. Please share yours as a comment if you’d like.

Take care, Love, Debbie