March-April 2021

Flirting with disaster

As a 76-year-old widow, I joined a dating website. What I found was anything but love.

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Illustration by Ellen Byrne

The first year of widowhood, I got sympathy. “Oh, you poor thing, you’re so alone.”

The second and third years, I got subtle hints. “Your husband wouldn’t want you to be alone.”

By year four, the messages were very clear. “You’re still alone? Haven’t you ever heard of online dating?”

So in January 2020 I signed up for Jdate, the site ostensibly for Jewish singles, for three months. It was excruciating. It was humiliating. I turned out to be a wallflower on the web. I only went on two dates—both with the same guy.

I should have known I was in trouble when the age category I was assigned to was 65 to dead. At least that’s how it sounded to me. But even then, the site was very optimistic. The first question Jdate asked as part of my profile was, “Do you want children?”

I decided before I started that I would not lie about my age, use an old photograph, pretend to be athletic or adventurous, or claim I was looking for true love.

Here is my dating profile:

I’m a 76-year-old widow and, yes, this is a recent picture. I am a mostly retired journalist who still loves a good story. I never covered hard news, but I am an expert on the Washington obsession with hair.

I am a blonde for life. I grew up on Long Island but repented in Greenwich Village. I am a reader, a writer, an involved grandmother, a volunteer and a partisan political junkie. No Republicans need apply. I can carry a tune but my kids wish I wouldn’t. I’d rather spend time at the Delaware beaches than travel to exotic places. I’d rather drink a Mike’s Hard Cranberry Lemonade than a martini. My friends say I’m smart, funny and unlikely to ever totally retire. They are glad that I am trying to be more patient. So far it isn’t working.

I’d like to meet an age-appropriate man who shares my passion for staying involved in everything around us. I’m not looking for a husband. I just want a great Saturday night date.

My ideal first date would be dinner, no phones allowed. I talk a lot but I promise my date would get a speaking part.

As soon as my profile went up, I had seven matches. Jdate rated them based on the site’s compatibility algorithm. The men ranged in age from 59 to 89. (I suspect a few “youngsters” sneaked into this age category for nefarious reasons.)

Most of the men in my age group were seeking younger women. Much younger women. Should I have asked for much younger men? My son, Jeremy, just turned 50. Did I want to go out with one of his fraternity brothers?

That wasn’t the only issue. My potential dates were all fitness fanatics. They said they loved to hike, bike, swim, ski, golf and otherwise engage in sweat-producing activities on an almost daily basis. The last time I hiked was probably in an outlet mall.

Looking over my prospects, I accidentally clicked on the “flirt” icon for Michael Number One. That’s not his real name. Many people on dating sites don’t use their real names. In my mind, I called all the men online “Michael.” I believe that half of the men my age are actually named Michael. The others are David, Steven, Stephen, Stuart, Stanley, Robert, Richard, Barry, Gary and Larry.

I signed on as “QWERTY Lady,” using the first six letters on a computer keyboard.

As soon as I realized my mistaken flirt, I messaged Michael Number One to say I didn’t mean to do it. Then I messaged him again to say I didn’t mean not to do it either. Michael Number One was a recent widower who’d made a New Year’s resolution to date again. After a few messages back and forth, he suggested we meet for dinner or coffee. I explained I was leaving town for a long weekend but would contact him when I returned. When I got home, I messaged Michael Number One again. He replied that he had been contacted by two other women during my brief absence and had set up two coffee dates that week. He said he wasn’t good at “multitasking” but he would message me again if neither of his coffee dates worked out. That was the end of Michael Number One.

Was I surprised that Michael Number One was searching for a date mere months after his beloved wife died? Not really.

Shortly after my husband, Benjamin, died, a close friend—another recent widow—and I were having dinner in Bethesda. A man we both knew who had recently lost his wife came over to embrace us. “We’ve all had a tough year,” he said. Then he turned to his table where his new girlfriend was waiting.

“Women mourn and men replace,” my dinner companion said.

Michael Number Two was from New York. He reached out to me on behalf of a “friend” who was enchanted by my online picture but too battered by failed romance to contact me directly. He offered his lovelorn friend’s email address and urged me to send him a message. Give a stranger my email address? No way. That was the end of Michael Number Two.

I had “flirts” from men in Louisville, Kentucky, and Orlando, Florida. Did they want me to travel to meet them? Send them money for a plane ticket to meet me? I didn’t respond.

I didn’t feel any connection to any of the other men the site suggested as matches. My daughter, Meredith, told me that I was being too picky. That I should have an open mind. I couldn’t expect Robert Redford. Even Robert Redford isn’t Robert Redford anymore.

So, on my third week of not dating I decided to be proactive. I sent the same message to several potential dates: “I’m probably too old for you. But let’s chat anyway. I’m new at this and I need the practice.”

Within hours I had a message from Michael Number Three in Virginia. My age was not a problem, he wrote. But he lived in Mount Vernon, Virginia, was a lifetime member of the NRA and an admirer of the 45th president. He did not think we were a good match. Goodbye, Michael Number Three.

Michael Number Four required that I love his cats. He was also adamant about not meeting a woman who was depressed or who had ever been in psychotherapy. Is there a Jewish woman from New York who hasn’t been in psychotherapy? He gave me his cellphone number. I called but he never answered. I like to think that the cats were purring too loudly for him to hear the ring.

I actually had a lively online dialogue with Michael Number Five. He was the only one who picked up on my “QWERTY Lady” reference and asked if I was writing about my online dating. Like several of the men I “met” online, he was not a dating app virgin. He was back on Jdate after a breakup with someone he met on the site. “There’s no story here,” he said. “It’s been done.”

We were scheduling our first coffee date when I offhandedly insulted his religion—the New England Patriots. I said that Patriots coach Bill Belichick always looks angry. That I had long suspected Tom Brady was partially bionic. Plus, Patriots owner Robert Kraft had been caught in a Florida massage parlor investigation. Charges were later dropped. But I thought Kraft was a sleazy guy. Michael Number Five was not amused. For a coach, winning is more important than smiling, he said. Kraft is beloved by Patriots fans. He is a major philanthropist. (Michael Number Five directed me to the Kraft philanthropy website.) He was certain that Kraft had been singled out by lecherous cops in Florida. I apologized several times for not understanding the seriousness of my spurious attacks on the Patriots. Michael Number Five expressed his outrage several times. After several more messages, we agreed that coffee was out of the question.

That’s when I consulted Sally Craig, aka “Sally Love,” an online dating “expert” from Takoma Park whose own experience inspired her to do her own stand-up comedy routine, a riff on senior online dating. She advised me to sign up on multiple sites. She had signed up for Jdate even though she’s not Jewish. She went out with 10 men before she found her soulmate, she reported. Sally sympathized with Michael Number Five. She couldn’t have gone out with a Yankees fan, she said. Sally’s true love really is named Michael.

Tell anyone that you are doing “mature” online dating and they have a story to share. It is always about someone else. A friend of a friend who found true love. A cousin who thought she found true love until her granddaughter recognized the picture of her online admirer as that of an Australian movie star.

For “silver singles” there are also poignant “in sickness and in health” stories. What happens when two people meet online, fall in love, and then one develops a chronic illness? If you previously cared for a spouse with a devastating illness, you may not be willing or able to do it again. “You don’t want to be a nurse or a purse,” a good friend of mine said honestly.

Then there are the painfully honest profiles of men and women whose spouses are in long-term care for dementia or Alzheimer’s disease. I learned of several who found great relationships with people who understood and accepted their situations.

Back on Jdate, I discovered that dating when you are over 70 can make you feel young again—but not necessarily in a good way. All of the insecurities I felt at 16 came rushing back. Before my first trial date, I changed my outfit three times. I met Michael Number Six for coffee at a Panera about 5 miles from my apartment. I followed the safety rules: Always meet in a public place for a short period of time and don’t use your full name. Michael Six was a nice guy, a man close to my age, and a New York transplant with an accent that sounded like home to me. He was balding in a good way—no comb-over. He didn’t know a lot of people in town. We agreed to go out on a “real date” a week later.

That’s when I really started to panic. I suddenly realized that I hadn’t specifically stated in my profile that I wasn’t interested in romance. What if Michael Six wanted to have sex? I wasn’t about to expose my saggy self to anyone. The last time I puppy-sat for my daughter’s Havanese, I freaked out when the dog saw me naked.

I sent off a quick email to Michael Six clarifying that I was only interested in friendship, not romance. He replied that was fine with him.

Michael Six and I met for our real date at the Silver Diner on Rockville Pike. I thought we would be eating there. My date said he really wanted to go to a nicer restaurant. The place he picked was at Rio in Gaithersburg—much closer to my house than Silver Diner. Michael asked if I wanted to drive myself and meet him there. That felt like un-datelike behavior. I said we could go together in his car and then he could drive me back to mine.

His car would kindly be called a classic. I am OCD about my car’s interior. Michael did not share this obsession. He said he had given up smoking years ago, but his car hadn’t gotten the message. Since the chosen restaurant was almost in my neighborhood, I offered directions for the quickest way to get there. He said he knew where he was going. After a few wrong turns, while he searched for an elusive traffic circle, I started yelling in a definitely un-datelike manner “turn right, then turn left.”

At last, we got to the restaurant. As soon as we were seated, Michael announced that the place was too noisy and he removed his hearing aids. This did not bode well for dinner conversation. But we tried. We made it through dinner, shouting about our histories, our families, etc.

He: This restaurant has a great selection of craft beers.

Me: I don’t drink beer.

He: Oh.

Me: Now that you’ve moved here, close to your daughter, you get to see your grandchildren more often.

He: They live in a townhouse. I can’t climb the stairs.

Me: Oh.

When the check arrived, Michael Six insisted that since he invited me, he should pay for dinner.

He pulled out his wallet and surveyed its contents. Lots of business cards. His driver’s license. No credit cards. I paid the bill. He wanted to write me a check. I said he could pay the next time.

Michael Six was still apologizing about the bill when we got back into the car. He once again assured me that he knew where he was going. This time I waited for only one wrong turn before I started barking directions. Finally, we were on Rockville Pike, a straight shot back to Silver Diner. Michael Six seemed to be having difficulty seeing the white lines. I started praying.

My nasty inner self was muttering, “First he can’t hear and now he can’t see.”

I was overjoyed to get into my own car and drive home alone.

Michael Six did text afterward to say he found his credit card and he again offered to pay for dinner. He is a very nice man. He deserves to find a good woman. Just not me.

That was the end of my adventure on Jdate. I did have to pay for an additional three months. Like many subscription services, if you don’t affirmatively cancel, you are automatically re-enrolled. When I found out, I made sure my membership ended.

Sally Love had advised casting a wide net. So I checked out Match.com. I created a profile. I just couldn’t force myself to sign up. There are a lot of fish in the sea, but what if I only caught snakeheads?

Match.com was still trying to tempt me with messages from men who wanted to meet me when COVID-19 ended dating as we know it. Match.com offered me a 50% discount. OurTime, an offshoot of Match for people over 50, also sent me emails about possible matches. I deleted them all.

Some people would say pandemic dating is the best of all possible worlds—you can “date” without actually having to meet someone in person. However, I haven’t had a pen pal since I was 8 years old. And I hate being on FaceTime and Zoom staring at horrifying close-ups of my face.

So I am quitting the game, withdrawing my name, ghosting romance. Maybe I’m selfish. I don’t want anyone asking me, “What’s for dinner?” Maybe I’m spoiled. I had a good marriage for 46 years.

Or maybe I’m just not ready. Ask me again when I’m 80.

Leslie Milk was the lifestyle editor of Washingtonian magazine for 32 years. She is the author of It’s Her Wedding But I’ll Cry if I Want To: A Survival Guide for the Mother of the Bride.