The Tenth Time Is The Charm

If at first you don’t succeed, try, try again. That’s the lesson that Lisa, one half of this week’s Love Letter couple learned back in 1993. 

She was working as a speech language pathologist at school when she met her coworker Marilyn. Marilyn was a substitute teacher at the school, but she had given herself a more important job: finding Lisa a man. 

Over the course of the school year, Marilyn set Lisa up on nine dates, none of which worked out. Lisa was just about ready to stop taking Marilyn’s suggestions, but she agreed to meet Chris, a recent widower who was trying to get back into the dating scene. 

Marilyn claimed to have known Chris for years, and insisted that Lisa had to get to know him. What Lisa didn’t know, however, was that Marilyn and Chris had only met on vacation a few weeks earlier. Still, Marilyn’s perseverance paid off. Thirty years later, Lisa and Chris are still together. Here’s their story. 

How’d you two meet? 

Lisa: I’d been working with a substitute teacher for just a couple of weeks, and Marilyn made it her mission to set me up on dates. I don’t know why, but she was determined to get me to meet somebody. She set me up on a couple of blind dates that didn’t work out. Then she came back from spring break and she said “I’ve got the guy for you. I’ve known his family for years, but haven’t seen him in ages. He’s perfect, you’ve gotta go out with this guy.” 

And I said “Okay.” And then she told me he lived almost two hours away and that he had been married. And I said “Okay…” And then she told me that his first wife had passed away. And I was like “Really? I don’t know about this.” But she basically harassed me from April until probably around June when the school year ended to talk to him on the phone at least. 

How many dates had she set you up on by this point?

Lisa: She had literally set me up on nine terrible dates. 

And you were still giving her a chance? 

Lisa: I wasn’t giving her much of a chance with this one. I did have some fun dates, it’s just the guys never worked out. This was the tenth guy she tried to set me up with. So when the year ended, I finally said that she could give him my phone number. And he called and we talked probably all of July and most of August on the phone. And I finally agreed to let him meet me for a date. 

How’d the intro go from your side of things, Chris?

Chris: I had decided to go on a vacation by myself out to Long Island. I wanted to get away from a bunch of stuff that had happened. My first wife passed away in a car accident after about a year and a half of marriage. It was a great marriage, and I missed it. 

I tried to date. Back then, it was basically either somebody you knew or you went to a bar to try to meet people. I was failing miserably because I’m not a very social, outgoing person. 

My introduction to her coworker happened by accident. She was trying to tell me that she had a girl for me. And I said I wasn’t really interested, that I was on vacation and dating was terrible for me. 

But we were there a week or two together and she kept hounding me. Eventually I said “Maybe I’ll give it a shot.” At that point, I knew Lisa lived two hours away, so I was like “What’s the worst thing that could happen? I never see her again after I talk to her?”

When I called Lisa on the phone it was so easy to talk to her, we had a really great conversation. It worked out well and I wanted to meet her. And she agreed to meet. 

Lisa: You might have picked up on Chris’s story that Marilyn told me that he was a family friend who had known the family for years, since he was a kid. But he actually met them over April break because their boats were docked next to each other! So she knew him for like seven days. 

So she had exaggerated just a little bit in her pitch to you?

Lisa: She totally lied to me about how well she knew him! Our first date I had invited him to my apartment where I lived alone because he was this close family friend. And while we’d been talking on the phone somehow that fact never came to light. So he could’ve been a serial killer and that could’ve gone very poorly. 

What did you do for your first date? 

Lisa: It was a nine hour date. He showed up at my apartment. We had the best grilled cheese sandwiches ever. I lived up in the Hudson Valley, so we went to the Vanderbilt mansion, the Roosevelt estate, we went up to Kingston and drove around and talked and saw the sights. And then when we got back to my apartment we decided to get some dinner. 

Chris: I brought flowers. I was selling hardware at the time, so at the Vanderbilt mansion I showed her my expertise in hinges and doorknobs. I probably bored her to death but she was kind enough to actually seem interested in what I was talking about. And when the end of the night came it was just a kiss goodbye and then I drove two hours in the dark home. I couldn’t wait to get back and see her again. 

Do you have any advice about blind dates for our readers? Lisa, in your case it seems like the tenth time was the charm.

Lisa: It’s like they say, you’ve gotta kiss a lot of frogs before you find your prince. I think that’s true. I was certainly open to going on these dates, but I also didn’t waste my time if I didn’t like the guy or we didn’t have a lot in common. I didn’t waste my time dating multiple times, I could tell pretty quickly if I liked somebody or not. 

But my number one piece of advice is don’t let a virtual stranger come to your apartment! Meet them in a public place. I told both of my daughters, because now they go on dating apps, don’t meet anybody in your apartment. 

Chris, at the time you were obviously in a place where you didn’t want to date. Do you have anything you might share with our readers when it comes to staying open to the possibility of something new?

Chris: If it wasn’t for meeting Marilyn, I would probably still be single. The reason I say that is because I wasn’t happy with the way the dating scene was going for me. I needed that kick in the butt to get going. 

I think that for somebody out there that’s not dating or not an outgoing person, it helps having somebody set you up on a blind date and take a risk. I’m a very straight kind of guy in the sense that I don’t like to veer off the beaten path. I don’t like change and I don’t like risks. So taking that call was a big risk for me. But it panned out to be a wonderful thing 30 years later. 

And how did things with Marilyn end up? Did she stay a part of your lives?

Lisa: Unfortunately, very sadly, she passed away recently. But we stayed close with her for a long time. She had a seat of honor at the parents table at our wedding. And we kept in close contact with her. I wasn’t the only coworker who she tried fixing up, but I think I was the most successful.

🤔 Poll of The Day:

📊 Last Week We Asked…

“Can you instantly tell if someone is a good potential partner?”

• 35% said “yes, I can tell right away”

• 65 % said “no, it would take some time”

And one meet-cuter shared: “For me, it took me several dates to decide if my current partner and I were a good match. I had to really analyze how he treated others and how he did in weird/different situations. I also wanted to see if he could match my goofiness, and he did!”

Do you or someone you know have a meet-cute story for the Love Letter? Get in touch here!

Interviewed and transcribed by Nicolas Vega. This interview has been edited for length and clarity