My Last Five Dates: Phone Porn, Porch Makeouts, and A Hot Younger Man

Finding the path to long term love in your 50s? That’s tricky. Especially under quarantine.

My Last Five Dates: Phone Porn, Porch Makeouts, and A Hot Younger Man

By 49, I had two ex-husbands and five rotating boyfriends—at 50, I got serious about wanting a soulmate an emotionally healthy partner. I used the downtime of the pandemic to work intensively with a teletherapist and a sex/love/leadership coach and under their tutelage, I decoded my destructive pattern (wildly charismatic, emotionally unavailable men) and started using my journalistic skills to comb the planet for a stable, psychologically grounded partner.

This is when my love life got seriously complex. Fooling around with destructive, dynamic partners in your 20s, 30s, and 40s is painful, but easy—like falling off a cliff. Finding the path to long term love in your 50s? That’s tricky. Especially under quarantine.

Jim*, a divorced 55-year-old Ivy League doctor, came highly recommended by two long-married friends. In my post-50 dating life, I Google ex-wives as a shortcut to sussing out compatibility and I shrieked when Jim’s ex popped up on my screen—she seemed old. So I dressed in my cutest sundress smock and cowboy boots, and drove two hours for a Covid-safe outdoor breakfast date with Jim. He had on hiking shorts and Birkenstocks, and his bare feet were so translucent, I thought he had on white socks. But the conversation was light and interesting, and we went for a glorious, sunshine-y walk afterwards. He asked for a kiss. Muttering about coronavirus, I gave him a hug instead. As I drove home, I thought…maybe?

By the time I rolled into my driveway, his texts had piled up.

Did you have a good time?

Yes. Would love to see you again.

How was I supposed to know you had a good time?

Because I did…I smiled a lot and hugged you goodbye.

Did you like my shirt?

I scrunched my brow trying to remember his shirt. It was dark green with Hawaiian pineapples. I’d seen one like it at Walmart a few days before. Before I could reply, Jim kept up his end.

How was I supposed to know if you liked my shirt when you didn’t say anything about it?

I bought it just for you.

His shirt? After I’d dressed in my first-date best and driven TWO HOURS to see him? Given my own swiss cheese neediness, I knew not to sign up to be his 24/7 self-esteem machine. Next.

Ethan’s* Facebook request turned up shirtless pictures, which is often bad news, but Ethan sported washboard abs, a tanned chest, and an unlined face. Our flirtations quickly turned raunchy. He was 28, fresh out of the Israeli army, and had a penchant for older women. He began supplying me with personalized porn via What’s App from Tel Aviv. Early morning erections, hard-ons after his workout, quick peeks below his swimsuit waistband, all narrated in a sensual Israeli drawl. He said I could share the videos with friends so for the next few weeks, my phone and I were popular Zoom cocktail guests—especially with my 50ish married pals who hadn’t seen anyone but their husband’s dick in 30 years.

You can allow yourself only a certain amount of shallow eroticism when looking for a partner. So I started having FaceTime dates with other men: an FBI agent from Texas, who offered me his “best 10%,” explaining he had to keep the remaining 90% for his local girlfriend, who was younger and hotter; the charming Mr. Montreal, who eventually called me a “cochon” in French thinking I wouldn’t know it meant “pig” in English; a lawyer, ten years older, fresh out of a long, sad marriage, who couldn’t stop comparing me to his ex. Next, next, next!

I got an email subject line from Dan* that read Let’s Skip the Small Talk—Marry Me and Move to Hawaii. Which I have to say was a good start. What followed? Long intellectual correspondence, late into the night and the discovery that we’d been to the same Rolling Stones concert at the Capitol Center in 1982. How could a man I’d never met know me so well?

As the frosting on the cupcake, Dan said his amicable ex-wife would vouch for him, and he gave me her number. My dating fantasy is to check references with the one person on earth who really knows your potential soulmate so I dialed Janet immediately.

She was lovely. “First of all, you should know Daniel really needs friends,” she said, which is the second scariest reference you can hear about a potential partner. “Next, I’m not his ex-wife. I’m his wife,” which is the first. They’d been separated for five years following a family tragedy and decades of Daniel’s untreated alcoholism. To this sisterhood candor, I was speechless, first with shock, then gratitude.

My advisors suggested dating closer to home, so I could check references a bit more readily. Conveniently, Tony* showed up in my Instagram feed. He lived a half-mile from my condo and his white Audi TT was the chick version of his black Porsche. He worked in IT intelligence and had a government background, which in DC means CIA. He loved his sailboat. His top travel destination was Positano, my favorite Italian village. It was fate!

We went for a socially distanced walk and ended up making out on his Georgetown front porch in view of at least a dozen passersby and neighbors. He was eight inches taller than me, so I nestled nicely into his chest. His beard was scratchy, his hard-on felt huge, and I was all in.

Two days later, driving my old minivan instead of the tell-tale TT, I stopped at a red light and watched in utter amazement as Tony, one hand clutching a pretty brunette, the other holding the leash of a bulldog, ambled across the street four feet in front of me. When I’d stopped hyperventilating, I called him. “That’s my wife,” he said. Well, at least he was honest.

My radar for spotting unavailable men was getting sharper, and the coaches instructed: in addition to dating local and checking references, get to “no” fast. Stop creating the perfect man by fantasizing about every male you meet. When a guy expresses interest, talk to him within a few hours. Ask blunt, revealing questions like, “Are you single?” Be transparent. Focus on flushing out fatal flaws or incompatibilities as quickly as possible.

Along came an East Coast entrepreneur with a passion for biking and birding, a Southern gentleman who wanted more than a local belle, a doctor whose wife had died of breast cancer. My new “transparency first” approach led to authentic, albeit brief, connections with each. All had their upsides, but something was missing, every time.

I kept returning to my favorite girlfriend advice: “It takes a special man to be better than no man at all.” The truth was, on this roller coast of dating and quarantining, I got to truly love living solo. For the first time in my life, I could see myself alone—forever. Picking what I wanted for dinner every single night, living where I wanted to live, washing my hair once a week, sprawling across the bed, not ever sharing a closet—it was all growing on me.

One Sunday in late summer, I worked on a vision board. “It’s no longer just a dream” and “Get closer” and “Getting warmer” were the random headlines from magazines that drew my subconscious. I glued them onto posterboard and dreamed of my future.

The next day, out of the blue, I went on a hike with a recently-divorced dad I’d known for 15 years. He was more handsome than I remembered. Funnier, too. In breezy conversations, we touched on the joys of grandkids and the pain of ending a marriage. I felt butterflies, not fireworks. I failed to flush out any fatal flaws or current wives.

We’ve been on at least 100 pandemic dates since then. We’ve never been to a movie theater together. Or a party. Or a work barbecue. He’s not seen me in a dress. I’ve seen him buck naked or in sweatpants more than slacks. However, the pandemic has afforded unlimited time for talk and sex, so there’s that.

My cats like him. My kids think he’s the one for me. Even my ex-husband thinks he’s the one for me. And most importantly, I think he’s the one for me. You might conclude that the first date with him was the most important one. However, the time I invested to change my dating patterns, explore all the wrong possibilities, and face being on a lifetime date with myself? That, actually, was the most important date of all.

*Names have been changed.

Leslie Morgan is the author of the New York Times best-selling memoir, Crazy Love. Her latest memoir (The Naked Truth, Simon & Schuster) explores femininity, aging and sexuality after 50. Visit her via her website, Facebook, Instagram, LinkedIn and Twitter.

This story originally appeared on: Glamour - Author:Leslie Morgan