How I Found Love At 55 By Abandoning My Rules

Detailed summary

Debbie Weiss is the author of the award-winning memoir “Available As Is: A Midlife Widow’s Search for Love.” Her writing has appeared in The New York Times’ “Modern Love” column.…

Two weeks after I’d met Randal for coffee, he called on the Sunday night before Memorial Day to say, “Tomorrow I’m going to spend the day driving through the Marin Hills to Stinson Beach with stops at my favorite restaurants along the way. Have you ever had breakfast at Fred’s in Sausalito?”

I hadn’t, and I didn’t particularly want to. My initial reaction: absolutely not. There’d be holiday traffic, parking nightmares, overpriced under-refrigerated shrimp sandwiches, and worst of all, an entire day trapped in a car with someone I barely knew.

Besides, I’d already signed up for my third hike of the weekend with my regular meetup group. I was looking forward to a familiar trail, chatting with the usual folks, then returning home to DoorDash for one and a new rom-com.

“Don’t feel bad if you don’t want to go, I’m going anyway,” he added, perhaps sensing my hesitation.

I considered. His dating profile had not looked promising. Sure, he was tall, tan and trim with a cap of white hair, but he liked tennis and skiing, both snow and water. I don’t do any of that. His picture showed him shirtless on a ski boat. Not my type — both the shirtless part and the ski boat.

“I’m not as athletic as you,” I’d texted when we first started communicating. “I don’t think we have much in common.” I figured we’d be good for a couple of lunches.

But he’d been kind on our initial coffee date, so despite feeling fairly certain I’d regret it, I said yes. I offered to meet him at his place since it was on the way, but he insisted on picking me up, even though it would add an hour to his trip. That unexpected courtesy was a pleasant surprise.

Dating at midlife had felt like an exercise in masochism. Widowed for six years and having dated for five, I was done trying to play well with others. I’d stopped marketing myself as more fun than I actually am, and it was a relief to settle into a comfortable rut of limited socializing, a meticulous home and much intellectual snobbery.

I was done with guys asking…

Opening of the article, excerpted from HuffPost. To read the rest, open the article on the publisher's site.