I don’t know how to hook up. It’s supposed to be easy. Isn’t that the appeal? No strings attached. But my attempts come riddled in knots.
We didn’t “hook up” back when I was coming out and supposed to be “sowing my wild oats.” We had one-night stands with phone numbers scribbled on pieces of paper that got lost, often intentionally.
What I know of the good old days is based on accounts from friends. I didn’t give off one-night-stand vibes while leaning against the bar, squeezing a half-dozen lime wedges into my bottle of Corona. If I gave off any vibe, it was boy-next-door, with any measure of sex appeal flatlined. I’ve been hookup-challenged since before it was even a thing.
I’m not supposed to be hooking up at all. I’m sixty-something—no need to be more specific. I should be in a meaningful relationship. I’ve yearned for them. I’ve had them. I’ve sucked at them.
Between doomed relationships, I’ve had long periods of being single. This didn’t mean I was a swinging bachelor, an expression even more dated than I am. I once went an excruciating period of fourteen years without sex. I went on more than a hundred coffee dates, almost all of them extending well past the time we’d finished our venti whatevers. I was a great conversationalist, but guys kept telling me there were no fireworks. Who expects bottle rockets at three in the afternoon?
Before getting into another relationship—if another should come along—I decided I needed to explore my sexuality, learn a few things, gain confidence, and lose the prude aura.
Since I live in Canada, my exploration would begin on a visit to Seattle. A foreign country, everyone a stranger, everything a one-off. My trip preparation included overpacking, googling the best doughnuts, and connecting with a couple looking for a three-way.
I’d never been in a threesome. I suppose it’s been a fantasy. Still I wasn’t actively seeking a ménage à trois. Saying it in French makes it sound so cultured; a little something to sandwich between brushing up on Degas and reading Voltaire.
Several days beforehand I logged into a respectable dating site, one that doesn’t allow dick pics. I changed my search area from Vancouver to Seattle. I sent two messages.
The first was to a guy who sounded a lot like me: an active cyclist, into the arts and social justice. His bio was written in complete sentences. Relationship material. Never heard back.
But I also came across a profile I only clicked to test my reading comprehension. The profile belonged to two first names like Jimmy Bob, but with an “and” plopped in between. I’d never seen two guys sharing one profile on this site.
Relationship status: living together; wanting to date but nothing serious. They were seeking a man or another couple for “friendship and exploration.” They wanted “a good, safe time that satisfies the desires and needs of everyone.”
I reread the profile. I concluded that “exploration” didn’t refer to space travel or even a Mount Rainier hike. They wanted a friend with benefits.
I messaged. They replied. We exchanged a series of messages that mentioned spending the night and even going to Hawaii together. Whoa. Benefits first.
We met on my second night in Seattle. Dean, who’d been the one messaging, greeted me with gleaming blue eyes and a broad smile. “Andy’s in the shower,” he said. Surely a routine. Andy would emerge in a towel, if anything. Let the exploration begin.
The shower took a long time. Had I been more forward, I’d have asked: “Am I supposed to check on him or do we both do that?” Instead I sat back in the armchair I’d chosen in lieu of a spot on the sofa beside Dean.
We had a classic coffee-date conversation, talking of families, of places we’ve lived, of authors we like. There were no awkward pauses. On a couple of occasions, Dean regarded something I’d said as profound, repeating it, nodding, smiling. It hadn’t occurred to me that foreplay would involve providing epiphanies.
Andy emerged, fully dressed, and sat in the armchair facing me. Dean said: “I haven’t told Andy why you’re here. Just that we’re having a guest.”
Was I the only one feeling awkward? I couldn’t read Andy’s face. Was this Dean’s fantasy? I got you something, dear. Do you like it?
I tried to bring Andy into the conversation. He was pleasant but chose his words carefully, every response measured. The chat continued to feel more alive between Dean and me.
Without a single kiss or caress, I could see why I’d always restricted thoughts of a threesome to the fantasy realm. The situation was uneven. Did Andy want any of this?
After talking at length, each of us remaining in our separate physical spaces, I tried to move things along. “So. … I’m wondering where things are at.” Dean was all-in and asked Andy: “What do you think?”
“I’m fine.”
Dean assured me this was Andy being enthusiastic, as if three cherries had just come up on a slot machine. Still we remained in our places and the conversation turned to Hawaii. Where did my hookup go?
Finally I headed out. “You guys need to eat. And you’ve both got to work tomorrow.” I’d gone from friend with benefits to mother. I added: “You need to talk without me being here.”
Three hours after arriving for my very first three-way, the only physical interaction involved a pair of goodbye hugs. “I’ll text you,” Dean said.
There was a message waiting when I got back to the hotel: “We think you’re wonderful.” Words I’d hoped to hear at the end of my first experience, but I couldn’t help thinking I’d botched the threesome. Our ménage à trois was missing the entrée. As much as I’d been concerned about Andy’s wants and needs, I’m the one who didn’t get what he desired.
I’ve still got so much to learn.
Gregory Walters is a writer living in Vancouver, BC. His essays have been published by The New York Times, CBC, The Globe and Mail, The Advocate, Little Old Lady Comedy, Next Avenue, and Funny Times. He writes a weekly blog, Aging Gayly, about mental health and being an older gay man. He’s on Instagram at @rxtraveler.
