MWC Honorable Mention

At 40, I Was Scared to Enter the Dating Pool Again

Plunging into online dating is a daunting experience

One of the kids in my swimming class was terrified of the deep pool. I found his mother sitting poolside and asked if he’d had any traumatic experiences that might have caused it.

“No,” she replied. “It’s me. I’m afraid of the water. I won’t even go in up to my knees.” She’d had a near-drowning experience in her early twenties and hadn’t been in the water since. To help her son with his fear, though, she agreed to work with me on her own.

That’s how I felt entering the dating pool again after 15 years of marriage — I was too afraid to even go knee deep.

My close group of friends after divorce were all single women. They were younger than me and using Tinder most weekends. They made it look easy and, hanging out with them, I started to wonder if I was ready to get my own feet wet. The idea of dating again after a failed relationship was scary but, after 15 years of marriage, dating had also changed. I hadn’t dated much at all before marriage. I’d had two long-term boyfriends in my twenties and then married the third.

Tinder felt like launching off the high-diving board. Except it wouldn’t be a graceful streamlined entry into dating. No. I was convinced I’d be the beginner diver executing a painful and embarrassing belly-flop.

My friend Nicky showed me her Tinder profile. “Go on. Pick a few guys for me. I don’t care,” she said handing me her phone.

“Seriously? Which way do I swipe again?”

My friend laughed and demonstrated, swiping her finger across a photo of a cute guy up a snow-covered mountain. A body-confident, fierce woman in her late 20s, Nicky treated dating with the attitude of an Olympic diver — jumping headfirst off the edge of a 10-meter diving-board couldn’t phase her. If the water was cold and you ended with a bad score, there was always another day, another date.

I picked three guys for her, surprised by how many normal-looking people there were to choose from. I’d heard horror stories in Facebook groups and expected much worse. Perhaps it was just a good day? I handed back the phone. “I’m still not convinced.”

There were several things that scared me about online dating.

Would my dates expect me, a woman in my 40s, to be experienced? I certainly didn’t feel it. And if I figured out the dating apps, weeded out the creeps, scammers, and weirdos somehow, and text-flirted my way to an in-person date, what then? Were there rules I didn’t know? Were there expectations on how physical we’d get, or what we’d do? My friends seemed comfortable negotiating around casual sex and dates with strangers, but I felt clueless.

The woman I helped with swimming had been quite traumatized by her near-drowning experience, so the first exercise I gave her was a simple one. All she needed to do every day for a week was practice holding her breath. If she could manage it, I suggested holding her breath in the shower with her face in the water. Small steps.

I’d met my first husband online. We stumbled across each other, not on a dating site but in a chat room. We talked online and then on the phone: long conversations into the night, a curly phone cord pulled across the hallway. I didn’t even see a photo of him until a month after we’d “met”. We were married for over a decade, but obviously, things didn’t end well and it put me off looking for love again in the same way. Perhaps this time around I needed to learn to hold my breath before I took on the deep end of online dating. Small steps.

A cute 20-something stranger boldly asked for sex in a hotel. A “friend” propositioned me over dinner. An older man texted me at a work conference at 2am — all he wanted was someone to spoon.

After years under the invisibility of marriage, I was suddenly exposed. I felt naked, and completely unprepared to get that way with a stranger. I turned them all down, wondering what I’d re-entered into; questioning if it was me somehow — was I giving men the wrong impression?

I’m sorry, I was just being friendly. Even if you’re great in bed, I’m not attracted to you in that way. I’m sure you’ll find someone to cuddle.

I’d only been divorced a short time. Did I have to jump straight in? Shoulders back, head high, on your marks, get set, go.

I felt too vulnerable. I wanted slow dating. I wanted elbows on the table, leaning in close to talk in a noisy restaurant; fingers laced around the handle of a mini-golf putter, laughing about our failed attempts at a hole-in-one; sitting side-by-side on the rocks at the beach, watching the surfers and eating fish ‘n chips. I wasn’t ready for a committed relationship yet, but I at least wanted an endurance event, a 500-meter swim. Not a sprint to the finish in our first conversation.

The cafe is crowded with musicians cradling their guitars, eager to take their turn at the open mic. The rest of us sit in tight circles, hoping at least some of them will sound good, and that alcohol will make the rest sound better. I catch his eye across the room; it’s 15 years since I’ve flirted with a stranger, in any serious way. Apparently, it’s not a skill we lose. Like swimming perhaps. My body remembers how long to hold his gaze, when to turn away and submerge into the conversation around me. One, two, three, breathe.

He turns his chair subtly to face mine, but stays in his own lane, sips his drink, watches the next singer. Watches me.

His group of friends stand to leave, and I know they’ll need to pass our table. He’ll need to pass me. Don’t ask for my number. Don’t say anything. He’s cute, but I want small steps. A graded pool where I can enter at the shallow end and tiptoe my way in.

I hold my breath. Hold his gaze. He nods, smiles shyly, walks past.

One more step into the deep. I let the water lap at my knees.

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