Some Things I Never Do When Dating After 50

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It was the New Year of 2020 and I lined up a series of first dates using Bumble, OK Cupid, and Tinder. I booked back-to-back dates with two different Pauls; coffee with a cute guy that requested pictures of my feet; drinks with a comedy writer; and some others.

Other than the Pauls, the others cancelled or ghosted. One guy even texted that he was giving it another go with his ex-wife. Then, Paul #1 cancelled our second date saying he didn’t really have time for dating.

I felt like a dating pariah.

Then there was Tim.

He was handsome, sexy, and had a cool job. We flirted back-and-forth on the dating app. We exchanged cell phone numbers. And because I felt horny and desperate, I texted him first—something I never do.

Me:  It’s Ginny.
      From OK Cupid.
      (Didn’t want you to confuse me
      with all the other Ginnys you know ) 😉

Tim: 😁 How bout we meet at The Irvington?

Me:  You’re taking me to a hotel on our first date?

Tim: I didn’t book a room.
      That’s 2nd date stuff 😜

I walked into the swanky hotel lobby bar dressed in black jeans, black shear blouse, black patent-leather boots, and my favorite red shearling coat, furry side out. It was a ‘look at me’ outfit. I felt like Carrie Bradshaw.

“Where do you live?” I asked, covering the ubiquitous ‘get-to-know-you’ questions.

“Chelsea, but you’ll never see the inside of my place,” he gibed.

“Why? What’s wrong with it?” I pitched back.

“Nothing.” He shrugged. “I just don’t take woman back to my place.”

We talked about dating. I expressed my latest frustration with men. He commented about crazy women.

“I’m not crazy,” I said.

“We’ll see.” He winked as he sipped his vodka tonic.

We found common ground when we discovered we both loved Martha’s Vineyard.

“I bet you’re an Edgartown girl,” he said teasingly.

“I may look like an Edgartown girl,” I defended. “But I’m more of an Oak Bluffs girl on the inside.”

He laughed out loud. We had more cocktails, some appetizers. Our legs pressed up against each other.

“You want to see my roof top deck?” He whispered between kisses on my neck. I liked him. He was challenging in a good way. But in my three years of post-divorce dating, I had never been to the man’s place—it’s something I never do.

We grabbed a cab and headed to his apartment. We shivered for exactly five minutes on his rooftop deck before retreating to his apartment. He had interesting art and an impressive collection of pots on display. I made fun of his Barbra Streisand records. He made me a drink. We ended up in the bedroom—my black jeans, black shear blouse, and black patent-leather boots on his floor.

In the morning, I gloated. “You said I’d never see the inside of your apartment.”

He laughed, and then climbed on top of me for round two. We made plans for a second date.

And then he canceled.

Tim: I can’t tonight. I feel
      like I’ve come down with the flu or cold.
      Brutal. Plus I’m exhausted and
      have to head upstate first thing tomorrow.
      Sorry. Let’s rain check 😉

Sick? My ass. I had had enough with these men cancelling, so instead of a “feel better” and moving on, I called him out.

Me:  Men are shits. I’m sure you really
      mean “thanks, but no thanks.”
      Am I wrong?

Tim: Whoa

That was the last I heard from Tim. It occurred to me that maybe, just maybe, he could have been ill. I had done something that I never do—I responded like a crazy woman.

Despite the outcome, I don’t regret the evening at all. It was sexy, fun, and liberating. And most importantly, it reaffirmed why I should never do those things.

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