Meeting a Lot of Mr. Wrongs to Get to Mr. Right

My Disastrous Dating Life 

Recently a good friend asked to have a Zoom chat to talk about how I ended up married after being single for fifteen years.

Ahh! I thought. This will be a great opportunity to pass on my fabulous wisdom. How lucky can my lonely friend get?

But by the time we got to our scheduled chat, I realized I had nothing profound to offer — just the same old clichés.

It happens when you least expect it.
Learn to love yourself first.
They won’t buy the cow if they get the milk for free?

The only thing I could think to tell him was that I had decided finding love was a numbers game. If I really wanted to meet someone, I had to do the work myself.

I wasn’t being invited to fancy balls like the sisters in Pride and Prejudice. I wasn’t being set up by a yenta like the daughters in Fiddler on the Roof. I could dance around my apartment with my broom singing Matchmaker Matchmaker Make Me a Match as much as I wanted, but it wasn’t going to get me a man.

Trust me. I know from experience.

But dating was never one my top skills. It was one humiliating experience after the next. And I never really got good at it.

Mitchell — The double downer

I adored Mitchell.

It was 1985. He was a handsome actor/waiter who worked at Joe Allen’s, a restaurant in the theatre district of New York City. He was twenty-four, the same age as me, but that was where the similarity ended.

Mitchell was tall with jet black hair, piercing blue eyes, a jutting masculine chin and an aura of sophisticated glamour. I was an average-looking receptionist at a video duplication company. On each of our three dates I was star-struck, as if I was having dinner with Cary Grant. Mitchell didn’t want to get too physical too fast — he wanted to go slow and really get to know me first. Of course, that unavailability made him all the more desirable.

I had big plans for our fourth date. I had decided it was going to be the date. That’s when things were going to go past third base all the way to home plate at my apartment. So when my phone rang, and I heard his deep voice at the end of the line, my heart leapt into my throat. Just the right position for me to choke on it.

“I can’t see you anymore,” Mitchell said. “I’m in love with someone else.”

What? But? Why?

He had never mentioned he was dating someone else. I had convinced myself he felt about me like I did about him. I thought we were going slow because I was someone special. But now I understood it was because he was marking time until someone better came along. I felt devastated. I felt stupid.

His call came only days before an already planned trip I was taking by myself to Key West. But instead of hiding in my dark bed and breakfast with the curtain drawn, I forced myself to spend the days riding my rented bike, swimming in the ocean, and watching the sun set while savoring a slice of tart key lime pie.

As my beat-up heart healed, I was almost back to my old self by the last day of the trip. Just because Mitchell isn’t attracted to me doesn’t mean I don’t have worth, I told myself. He just isn’t the one. Now I have room to meet the right guy.

I wasn’t only healed. I was enlightened.

I arrived home from the airport and hit the button on my answering machine.

“It’s Mitchell. Call me.”

I threw down my bags and dialed as quickly as I could. “Hi, it’s Keith.”

“I made a terrible mistake,” he blurted out. “I’m so sorry. I think I just got scared.”

It was a miracle. It was that point in the movie where you think Meg Ryan is going to spend every New Year’s Eve for the rest of her life alone and then Billy Crystal shows up. The girl was going to get the guy after all! Or in this case…the guy was going to get the guy.

Mitchell wanted to meet that very evening. I didn’t even unpack before I jumped in the shower and got ready. He had picked a restaurant that was a favorite of his on the Upper East Side. I lived in Brooklyn and it would take over an hour to get there, but I wasn’t going to let that get in the way. The long ride on the subway gave me time to dream about the perfect rest of our lives together.

Mitchell was already waiting at the table when I arrived. I rushed over giddily and sat down.

“Wow! You look wonderful tonight!” I said.

“I’m sorry. I just can’t do this,” he replied.


“I’m sorry. I thought I could, but I can’t.”

I had so many questions. Why did you call me after I had just gotten over you? What happened between the phone call and me arriving at the restaurant to change your mind?

But mostly I wondered. Why? Why can’t you love me?

But I didn’t ask any of these questions. I just sat there what my mouth hanging open.

“Okay,” I finally said with a defeated sigh.

“We can still have dinner together,” he offered.

“No….no…I’m kind of tired. I’m just going to go home.”

I stood and walked out trying to look like I was taking this all in stride when I really wanted to just curl up and hide under one of the restaurant tables.

I climbed down the steps to the subway and felt better just being underground and away from that awful experience. All I could focus on was being home in my bed eating Pringles and weeping loudly. I looked down the tracks impatiently and waited for the subway to come.

Twenty minutes later I was still waiting.

Thirty minutes later the platform was full of people but still no subway.

Forty-five minutes — no subway and I had to pee. The trains seemed to have stopped running.

I considered throwing myself onto the tracks and ending my miserable life by being tragically crushed under the wheels of an oncoming train like Anna Karenina, but realized since no subway was coming, I would just be lying on the tracks for a long time with people staring curiously down at me.

I finally made it home and Mitchell never reconsidered again. He got together with the other guy and they were a couple for several years. I have to admit that when I occasionally heard rumors of their epic fights, it gave me just a little pleasure.

And the loser is…

I wish I could say that was the worst of my dates, but it wasn’t. There were so many, I can’t even begin to pick the actual worst. Some contenders:

  • The guy who insisted on meeting me the same day I returned from a trip to Nepal. We had chatted for months, but he was in the neighborhood and wanted to have drinks. “I’m not at my best,” I tried to explain. “I’m really jetlagged.” “I’m sure you’ll be fine,” he reassured me. Wow. He seemed like a pretty understanding guy. I arrived bedraggled and bleary-eyed. Once I sat down, my jetlag hit hard, and I struggled to keep up with the conversation. Later he texted. “You are a nice guy but didn’t seem very engaged in our conversation. Thanks anyway but not really interested in meeting again.”
  • The one I went out with only a week after I’d decided to stop drinking who wanted to meet me at a wine bar. I didn’t want to seem high-maintenance and ask him to pick somewhere else. Besides, you can drink other things at a wine bar, right? Apparently it was VERY important to this guy that a date drink actual wine at a wine bar. He felt I met him under false pretenses. That was the last I heard from him.
  • The blind date I was set up on by a famous celebrity I knew. (Who doesn’t love a celebrity friend?) It was an okay date but no chemistry. A week later, the celebrity called and asked why I wasn’t going on a second date. I told her he was very nice but there was no romantic spark. She got mad and never spoke to me again.
  • The date where I fought with the guy because he told me he had thrown a rock at a sick opossum hanging out in front of his apartment. During the same dinner, we got into a second fight because I told him I always put my clothes away in drawers when I stayed at hotels. “You are going to get bedbugs,” he said with certainty. “You don’t really know that,” I replied. “YOU ARE GOING TO GET BEDBUGS!” he insisted as if he was putting a curse on me. We both angrily agreed that would be our first and last date.
  • Then there was the guy I went out with for several months who kept falling asleep at odd times. I thought I just bored him until years later he confessed he had been secretly addicted to meth the entire time.

What doesn’t kill you forces you to keep living

So I was a terrible dater and had a lot of really terrible dates.

But there was something that kept me going. It happened after that date with Mitchell back in the 80’s. When I had finally made it home, I wanted to do anything but feel that gross pain of rejection. Maybe I should smoke pot or buy a pack of cigarettes or pour myself a huge glass of wine or two or three.

But instead I decided to do nothing. I was going to let myself experience the pain instead of numbing out. I lay on my couch and just felt it. I cried for about fifteen minutes, but then got kind of tired of that.

Then a random funny thought popped into my head. I don’t remember what it was anymore, but it made me smile and then actually chuckle out loud. In that moment, I realized that this pain I was feeling would not kill me. If I just let it play out, I couldn’t even sustain it for fifteen minutes. Learning that made me fear it less.

During the next decades of bad dates, I’d have to occasionally remind myself of that lesson. It would give me the strength and endurance to keep going until I finally met a guy who wouldn’t dream of throwing a rock at a sick opossum and has seen me jetlagged many times and still stuck around.

So, I suppose my advice to my friend or anyone else asking is to not let a little humiliation stop you from searching for what you want.

And just in case that guy’s right about bed bugs, don’t put your clothes in hotel room dresser drawers.

ABOUT THE AUTHOR Keith Hoffman lives in Lambertville, NJ with his husband Saul. You can read his blog at He currently has no celebrity friends.


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Keith Hoffman lives with his artist husband, dog and two cats in the small town Lambertville, New Jersey 72 miles outside of New York City. He has completed a memoir entitled The Summer My Sister Grew Sideburns.

4 thoughts on “Meeting a Lot of Mr. Wrongs to Get to Mr. Right”

  1. This is hilarious. It just made my day. I am glad it did work out at the end. I guess we just never have to give up on anything, no matter how hard it might be. You did prove it. Thank you so much for sharing. I really enjoyed reading it.


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