L.A. Affairs: He hadn't dated since 1989. Did a relationship with him stand a chance?

“I don’t want to go.”

“I get it.”

I was on the phone with my emotional support friend Jill, who was trying to pump me up to meet someone new despite her awareness of my latest soul-crushing connections. “You have had a challenging run lately, but you never know when it might turn around,” she said.

The idealist in me wanted to believe Jill could be right, but the realist in me wasn’t convinced. Despite delving into the app dating world in my early 50s with zero expectations and vowing not to be attached to any specific outcomes, I had grown weary from the process. But I was wearing heels and makeup and I’d blown out my hair in an effort that had felt Herculean ever since COVID. It would have been a shame for it all to go to waste.

I was meeting a date at Hugo’s in West Hollywood at 5:30 p.m. I left late because I was procrastinating, and then, thanks to L.A. traffic, got there at 5:45 p.m.

When I finally arrived after texting to let him know of my delay, I rushed up, trying to pull myself together. “I am so sorry.”

“Hi, you made it.” He got up for a quick hug and then walked behind me as I tried to figure out what was happening. He pulled my chair out for me. I acted as though this was an everyday occurrence. It definitely was not.

I had quickly learned to be prepared for dates to look worse than their worst profile picture; he looked even better than his best picture. The cynic in me was still on high alert for the red flags that were inevitably coming, but he was warm, with an easygoing demeanor, and very comfortable in his own skin. It turns out he was a very sought-after golf instructor who luckily didn’t care that I had never played.

“I like that you just reached over and ate one of my potatoes.” He was smiling and seemed genuinely pleased that I had done so. I hadn’t even realized I had scarfed down one of his potatoes, let alone without asking.

“I never do that. I must feel comfortable,” I said. Someone eating off my plate definitely annoyed me in most situations, but this felt different. I’m pretty sure I would have given him all of my potatoes had he maneuvered his fork in my direction. After he went to put money in the parking meter and actually came back, I was relieved. He later told me he was relieved I was still there when he returned.

“Am I talking too much?” I asked. I sometimes did that when I had nervous energy. “Not at all. I like learning about you,” he said.

He told me he had been in an almost 25-year marriage and, other than a few recent Bumble dates, he hadn’t dated since 1989. When he said he had no idea what he was doing, I told him I had been dating a lot recently and he was doing better than 99.9% of the men out there. I told him I hadn’t been in a relationship in almost 20 years, having prioritized my career for many years.

I was used to being interrogated about never having been married, but he didn’t seem to judge my choices. I told him about some of the most egregious dating offenses I had endured: he who suggested that we dine and dash and didn’t seem to be kidding, he who asked for business contacts after I declined a second date, he who took home my leftovers on the first date, he who contorted his body to go in for a kiss as I very pointedly went in for a hug. I could’ve continued late into the night.

He laughed and told me about his more run-of-the-mill dates, with whom he just hadn’t felt any romantic connection. One had cats, which would have been problematic since he was highly allergic. One might have been a hoarder.

It was quickly evident that we shared a similar sense of humor and prioritized the same attributes, such as honesty, kindness and a propensity for always trying to do the right thing. I also was pleasantly surprised that he ordered an iced tea; I had stopped drinking alcohol a month before.

He told me he went on Bumble on a whim because it scared him, which I admired. It was endearing that he had stepped outside his comfort zone, especially after not having dated since he was 21. After talking for more than three hours, he walked me to my car.

He gave me a quick hug, opened my car door and said, “Talk to you soon” — and then quickly walked away after patting me on the shoulder. It was the best first date I’d ever had, but the “Talk to you soon” really threw me. Was this a blow-off?

Later, while I was obsessively pondering whether I would ever hear from him again, he texted to make sure I got home safely. “I failed to tell you how great you looked tonight. I hope you can forgive me. I’m falling on my sword.” This could have felt cheesy, and yet I melted, a testament to his genuineness.

The next day I went on a horrible first coffee date that had been previously scheduled. It lasted 40 minutes, about 37 minutes too long. When I got to my car, I found Mr. Perfect First Date had texted again. “I’m sure there’s some stupid rule about texting you today, but I wanted you to know I had a really good time last night,” he wrote.

“In that case, should I have waited at least five hours to text you back?” I replied.

“Ha, yes, and I shouldn’t be sending you this response right now.”

“Should we agree that we don’t have to play by any rules?” I asked.

I was so tired from all the complicated dating noise that seemed to persist even at my age, so I was relieved he wasn’t playing games.

“Yes, please, “ he replied.

“Perfect, we just solved all the world’s problems.”

I didn’t hear from him for a couple of hours and then: “The next challenge is me asking you out again. Forward of me I know.”

“Let me think about it,” I teased. I let about a minute pass. “Kidding, yes, that would be lovely.”

“Phew, I was worried.”

We still don’t play by any rules. And I still don’t know anything about golf.

The author is new to writing after more than 20 years as a creative executive in the entertainment industry. She lives in Los Angeles with Mr. Perfect First Date. She’s on Instagram: @jobethplatt

L.A. Affairs chronicles the search for romantic love in all its glorious expressions in the L.A. area, and we want to hear your true story. We pay $400 for a published essay. Email LAAffairs@latimes.com. You can find submission guidelines here. You can find past columns here.