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 favourite 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 socialising, a meticulous home and much intellectual snobbery.
I was done with guys asking why I didn’t like to stay out late, while I wanted to ask why they never cleaned out their refrigerators. I was tired of men who thought I should change to suit them or who saw me as a sounding board for their woes. If younger guys wanted sex, older guys wanted someone they could complain to. Apparently, a diatribe against their ex-wives plus a demand that I adjust to their schedules constitutes foreplay these days.
I had my rules too. A real prospect should have at least one graduate degree from a reputable institution, an impressive career, and not wear Teva sandals (they just don’t look good on anyone). He should read actual books and not sneer at the word “fiction”. He had to get my sense of humour and, most importantly, not be patronising.
I was done with men acting superior to me, from the overloaded contract lawyer I met who didn’t do litigation (which I had as a lawyer) to the polyamorous doctor who scoffed at my monogamous nature but at 60 had never been in a long-term relationship.
Still, I was lonely. My rules had not yielded love.
Rather, I was setting myself up for the pretty limited life of an introvert and homebody who was done venturing out of her comfort zone.
When Randal picked me up on Memorial Day morning, I almost didn’t recognise him. The mild-mannered realtor in the plaid sports coat and designer loafers I’d met for coffee turned out to be a buff beach guy in a tight blue T-shirt driving a vintage convertible. More importantly, he was still kind.
The day was a blast, from the eggs benedict at Fred’s to the impromptu dinner at the Spinnaker, despite the crowds, the traffic and the heat. He graciously accepted my offer to navigate from my phone when he made a wrong turn. It was a sharp contrast to guys who’d acted as if having a woman direct them from a maps app was an admission of erectile dysfunction.
The date lasted 12 hours, with two meals, a champagne stop, and a performance by a bad country band. We were not bored.
Our dates continued from there, and I found myself outside of my cherished comfort zone. We had late dinners after his workdays, even though I liked to eat by 6pm. We even went for drinks afterward, even though I didn’t like to be up late on a hiking night.
One date early on involved an overnight to Carmel with separate rooms because he’d read my blog entry about missing that area since I lost my husband. Another trip involved a few days in Santa Cruz in a two-bedroom cottage. Both plans seemed premature given how long we’d known each other, but they brought us closer and, to my surprise, they were really fun.
I began to notice how often my first response to his ideas was no. Because of traffic. And parking. We’d get home late. I’d miss my regular yoga class. But I started wondering whether my objections were really less about convenience and more about protecting myself from disappointment.
Eventually, when Randal suggested something, I tried pausing before answering negatively and listing all the things that could go wrong, a holdover from my marriage when my late husband didn’t like being delayed getting home. Usually, saying yes led to memorable days together.
As we spent more time together, I saw that we had similar values. We both wanted a love that lasts, even though that isn’t easy, especially when you’re older and already set in your ways.
We wanted someone who’d be there on the hard days, which for me meant my late husband’s birthday and when my house was breaking down. Randal won my heart on our Carmel overnight when he helped me decide on a bid to replace my damaged air conditioner even though we were on a romantic outing. He understood that life continued outside of the bubble we had created when we were together.
For Randal, hard days meant grieving his mother’s recent death. We were both looking for a grown-up.
Randal gave me a little picture book of beach drawings, which was truly charming. He is a visual learner who doesn’t read a lot. He is athletic, and gets up early to run or ride his bike as the sun rises. He’d send me pictures of sunrises, shades of pink sliding into orange above dark hills, usually accompanied by an upbeat message about having a great day. This was also charming although I do neither sunrises nor upbeat. He has a good job (no graduate degree), but he lives for skiing, being on the beach, and other passions beyond work.
Over time, I realised many of my rules came from a sense of insecurity. I’d wanted someone with a graduate degree and an impressive job because I felt like I hadn’t done enough with my own law career. I also wanted someone with similar hobbies because I was afraid that someone with different ones wouldn’t be interested in me. I’m a nerd, and I’ve never done well with athletes.
Worse, my rules had hardened into rigidity after years of being disappointed. When I’d first started venturing out as a widow, I’d been open to new people and experiences – to living differently than I had in my marriage.
But that had left me bruised because so many interactions with men felt like power struggles, as if they were seeing how much they could get while giving the least possible. I’d also lost many of my female friends from my friend group after one of them accused me of going after her boyfriend, even though he had reached out to me online without disclosing that he knew her.
By the time I met Randal, I was aiming for the life of a self-contained hermit, but he surprised me by genuinely seeming to like me as I am.
Despite being almost opposites, Randal and I have been together for eight years. He’s chill and occasionally a bit scattered while I’m Type A and often obsessive. He’s sincere, which was tricky at first, as my communication style used to lean towards sarcasm and vitriol. I had to be careful how I spoke to him.
I also had to learn a bit of patience, which I’m terrible at, having grown up with a single dad who was a physicist (our joke had always been that “patient physicist” was an oxymoron).
After three years, Randal and I moved into a new place together, and I was surprised at the joy of letting go of my old house of 27 years along with the memories that lived within its walls. Getting rid of things I used to cherish but that didn’t fit into our new home felt like opening a window in a stagnant room.
What surprised me wasn’t just falling in love after widowhood; it was realising how much of “who I am” was really just made up of inflexibility and routine. Rigidity isn’t an accomplishment – although it can be a defense.
I dealt with my own feelings of not having accomplished enough by going back to college for an MFA degree and writing a book. Randal was super supportive and picked me up after my evening classes. I encouraged his return to skiing after an injury, and he helped me decide to do yoga teacher training for my 60th birthday. We hike together sometimes and I’ve heard that Teva sandals are really comfortable to change into afterwards.
Falling in love didn’t require compromising my standards. I just needed to separate the ones that reflected my values from the ones that protected my fears.
It did require me to open myself up again to new experiences and abandon my cynicism, which had been quite well-earned over years of dating. But saying yes to one long date led me to companionship – and eventually love – at age 55 when I’d almost given up. Because love sometimes arrives disguised as the exact kind of day you’d normally avoid.
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. She writes about grief, relationships, and the unexpected turns of midlife on her Substack, The Hungover Widow. Find more of her work at debbieweissauthor.com.
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