A simple truth: Dating sucks. And dating over 50 comes with its own inestimable challenges. What used to be perky now sags. Hair grows where we don’t want it and disappears from where we do want it. If we’re lucky, we have aging parents. Some of us have children, still young or already grown. Some of us don’t. We’ve got our respective baggage full of broken hearts, unyielding habits, and not-so-unyielding expectations.

We’re all out there, trying and hoping. Because, bottom line, we don’t want to die alone. At least I don’t.

This summer I signed on to a free online site that has a decent array of educated and interesting men who suited both my fancy and my pocketbook. I’ve been on and off the scene for years. Whenever I consider trying again, I shrivel at the thought of crafting yet another peppy profile, much less plumbing through piles of “honest, independent” guys who in reality still live with their mother or their ex. Or profiles by Yankees fans. Or athletes who hike, bike, kayak, sail, jet-ski, and surf. I get tired just reading the list. Or the testosterone-laden men who say they love to kiss, cuddle, hug, make passionate love, or give full-body massages. Maybe this is a turn-on for some women. For me? Yecch.

I found a few of interest. And a few found me. The formula is basically the same. There’s the requisite initial exchange of “enjoyed your profile” and “seems like we might have a lot in common.” Then the requisite “are you an ax murderer if not let’s meet” phone call, followed by the requisite rendezvous at a mutually convenient Starbucks.

So, after the preliminaries, I ended up on three blind dates recently, all in the same week. Herewith my report:

 

DATE #1: MARK, THE HAIRY POLITICO

The Basics: 58 years old, tall, long white hair tied back in a ponytail, divorced, unaffiliated religiously, master’s degree, politically active, jazz musician, intellectual. Interesting profile. Points for perfect spelling.

The Pre-Date: Pleasant email exchange. No phone—just an agreed-upon date and time. Cut to the chase, I say. 3D yields more info than any profile or phone call.

The Setting: Outdoor table at a café on a sunny Sunday morning at 11:30

The Date: He’s waiting for me. I’m prompt. We shake hands and enter the café for takeout. He orders coffee and a blueberry scone. I get raspberry herbal tea. We pay separately. We sit outside. I lead off: “So where do you play music?” His voice is uncomfortably loud, which makes me self-conscious, as a handsome African-American man at the next table reading the New York Times can probably hear every word. One subject leads to the next. It is not a chat. It is a monologue. One hour later I know about his sister’s hysterectomy, his father’s phlebitis, his lackadaisical coworkers, and his views on green living and stem-cell research. He’s barely touched his scone. He hasn’t asked one question, even in a lull I decide to impose just to see what he’ll do. I go to the bathroom. Perhaps the break will give him a chance to remember he’s on a date.

I return. His scone and coffee are gone. “So, you’re a writer,” he says. “What do you write?” I say four sentences about my memoir-in-progress of being a teenager in Germany. He says, “Oh, Germany! I traveled in Germany once . . . ” and continues with tales of Berlin and Bremerhaven. I look at my watch. “Oh! It’s 12:43,” I say. “I didn’t realize it was so late. I’ve got to get going.” Pause. “Nice to meet you, Mark.” We stand up. We shake hands. “Take care.” We part. I might as well have been a cardboard cutout.

The Outcome: Mutual silence. Fine by me.

DATE #2: TONY, THE CLOSE WALKER

The Basics: 64 (which actually turns out to be 67), 5 feet 8, Italian Catholic, balding with white hair and a beard, divorced with adult children, songwriter, semi-retired businessman, marathon runner, fun profile with cute sense of humor.

The Pre-Date: Two emails lead to a phone call. He opens with, “So tell me about yourself.” I say, “Wow. That’s a broad question. Can you be more specific?” He says, “OK, tell me about your left leg.” I do. He asks, “Tell me about the last time you had your heart broken.” Oh, come on. Can’t we talk about the weather? I tell him I’d have to know him a little more before divulging my cardiac history. We set a date to walk around a local reservoir. “That way, after 40 minutes, if we don’t like each other, we’re done, but at least we’ve gotten some exercise,” he says. Points for directness.

The Setting: Thursday morning, the reservoir, a popular place for dogs and runners

The Date: I’m on time, at the golf course parking lot, inhaling secondhand smoke from the local golfers getting ready to tee off. No sign of Tony. Ten minutes later, he pulls up in a pickup truck, beeping. He waves. I wave back. He parks. “I just left a message on your phone,” he says, as he opens his arms wide for a hello hug. I don’t know him. I don’t feel like hugging. He’s late and he’s sweaty in his tank top and shorts, but he has a bright smile. His chihuahua, Margarita, bounces beside him.

It’s a gorgeous day and, despite the awkward start, we chat easily—I’m on the inside of the path, along the fence guarding the reservoir. He is walking close enough that I occasionally feel his bristly white arm hairs brush against mine. I edge away. He moves closer. It’s subtle. I try to accept that we all have different values about personal space. He learns that I see clients with drug and alcohol problems. He tells me he’s a recovering alcoholic. He’s glad I’m not judgmental. I feel the urge to put on my therapist hat but I suppress it. I’m off duty.

We run into a mutual friend—my neighbor, who runs a doggie daycare, knows Tony and Margarita from the path. We chat. He runs into another dog-walking buddy, Monica, and her two bulldogs, Ruby and Rhinestone. We sit on a bench. Tony sits too close. Ruby pees on my leg. After the 40-minute roundtrip, Tony wants to have coffee at the golf course café. I don’t. I’m sweaty and I need to change my pants. I tell him I enjoyed the walk. He gives me a sweaty hug goodbye. I don’t like hugging strangers.

The Outcome: I drop him a “thanks, it was nice to meet you” note, because despite the close walking, the age-fudging, and the tardiness, I want to keep an open mind. He writes back ten days later and tells me to call him if I want to go out again. We’ll see.

DATE #3: JONATHAN, THE EAGER DEPRESSIVE

The Basics: 64, tall and thin, shaggy dark hair, Jewish, former software person, now does nonprofit work, into meditation and literature, eclectic musical tastes, no mention of marital status, very long profile, perhaps too long

The Pre-Date: He emails me with a list of questions plus commentary on “things I like about you” and “things I like not quite so well.” I try to lower the volume on my “eek” radar. Just get out there, Debbie. You don’t have to marry the guy. We progress to a phone call on my suggestion. He talks nonstop for a half-hour. It’s late and I’m tired. I don’t care that he doesn’t ask me anything. I want to watch the Red Sox.

Two emails later, we set a date. By now, I know about his digestive problems, his psychiatric history, and his views on religion and meditation. He knows I’m female and a writer. I’m willing to give him a chance, God knows why. Oh yeah, I don’t want to die alone.

The Setting: 10:30 a.m. Friday at a Starbucks

The Date: I’m on time, he’s late. We both get hot water for our herbal teabags that we brought from home. I do not share my digestive problems. He does. We talk about meditation—we’re both longtime practitioners. He is smart. He looks gloomy, but he says he’s happy because he’s found a solution to his lifelong depression via a new dietary regime. He tells me about his first two wives and his third wife, who died of cancer. I empathize. He talks about death. I tell him I’d prefer not to talk about death. I want to talk about life. He says death isn’t depressing. I feel depressed.

He asks me questions. I tell him about my writing workshops and singing. After 90 minutes, I say I have to leave to get ready for work. Which I do. His face changes. He grins broadly, like a little boy, and asks, “Would you like to join me in evaluating this date?” “Excuse me?” I answer. “Let’s talk about how the date went,” he replies. I suppress the urge to laugh or flee, but somehow I feel a blog coming on, so I say, “Well, I have a couple of minutes, but let’s at least go outside—it’s so nice!”

We sit on a bench. He does not sit too close. He tells me that on his first date with his third wife, she asked him to evaluate the date. He says they agreed it was a “boring date,” then talked for three hours in the rain and fell in love. I sense he wants an encore. He continues, “Now this was the best date I’ve had in a long time, because I felt comfortable with you. You were on time. You maintained eye contact. You didn’t grill me like some women do, probing for information about finances and marriage, as if they’re going down a checklist.” (I’ve heard this before from men—that women approach a date like a job interview, sizing up the guy’s qualifications according to a specific paradigm.)

“Well, I enjoyed meeting you,” I say. “You seem very nice. At this point, I’m trying to be open, go out and meet a lot of people, but I really don’t feel like evaluating something that just happened three minutes ago. I’d rather just digest the experience and be in the present.” He says he appreciates my answer. I appreciate his forthrightness. I’m so done with this. He gives me his card and asks me to be in touch. I say, “I’ll let you know how things are going.”

The Outcome: He writes a thank-you email and follow-up about how his digestion is improving. I reply, saying I don’t think it’s a good match and best of luck. He replies, saying he is disappointed but respects my choice and says my future partner is a lucky guy. I smile.

 

Onward.

 

(NB: All names and some identifying information have been changed to protect the well-meaning but unfortunately incompatible.)