I had reached my breaking point with dating apps. Was it possible to meet someone genuinely normal? As I scrolled through the multitude of headlines on the Los Angeles Times—from California politics to the latest in entertainment—I found myself caught between the endless noise of expectations and disappointments in the dating scene. I was on the phone with my friend Jill, who had been my emotional rock during this tumultuous journey. “I understand your hesitations,” she said, trying to reassure me. “You’ve had a tough time, but you might be surprised how things can turn around.” Despite her optimism, I found it hard to shake my skepticism.
In my early 50s, I had entered the dating app world with an open mind, promising myself I wouldn’t get attached to any particular outcomes. Yet here I was, fatigued and fed up. I had made an effort that day—dressed up, applying heels and makeup, taking extra time on my hair—part of me knew it would all be for nothing if I didn’t go through with the date I had scheduled at Hugo’s in West Hollywood. Unfortunately, I was late thanks to traffic.
I finally arrived around 5:45 p.m. and immediately texted my date to let him know I was running behind. As I approached him, I felt a rush of both nerves and curiosity. “I’m really sorry,” I apologized as I tried to regain my composure. He greeted me warmly, rising for a quick hug and effortlessly pulling out my chair as I took my seat.
To my pleasant surprise, he looked even better than the pictures I had seen on his profile—definitely an exception to my past experiences where reality fell short of expectations. This man, it turned out, was a popular golf instructor, which I noted without any judgment about my complete lack of golfing experience.
His laid-back vibe was refreshing; when I reached for one of his potatoes without thinking, he laughed and said, “I like that you just helped yourself.” It was a small gesture, but it felt like an easy moment of connection. After our initial awkwardness, he left to put money in the parking meter—and I found myself relieved when he returned promptly.
As we delved into conversation, I wondered if I was dominating the exchange. “Am I talking too much?” I blurted out. He shook his head and insisted he enjoyed learning about me. Our discussions revealed we were both navigating the complexities of dating after significant past relationships—his nearly 25-year marriage and my own two-decade absence from romantic entanglements, largely due to prioritizing my career.
I shared some of my most cringe-worthy dating experiences, including a guy who suggested we dine and dash simply to be amusing, and another who had the audacity to ask for business contacts after I declined a second date. He chuckled at my stories, even sharing his own mundane dating encounters, which, while unremarkable, reflected a similar search for connection.
As the hours passed, we discovered shared values of honesty and kindness; both of us had stepped into this dating scene, albeit reluctantly, yearning for something real. He casually mentioned his decision to give Bumble a shot because it felt daunting, a quality I found endearing. When the night came to a close, he walked me to my car, offering a quick hug and saying, “Talk to you soon.” Part of me felt unsettled—was that a polite exit or a genuine interest to reconnect?
Later that night, my anxious thoughts were quelled when he texted to confirm I made it home safely, even apologizing for not complimenting my looks sooner. I couldn’t help but notice it was a charming move, one that could easily cross the line into cheesy, yet it landed just right with me.
The very next day brought a lackluster coffee date that felt like it stretched on far too long. Just when I was starting to question my dating luck again, my phone buzzed with another message from him. “I’m not sure if there’s an unwritten rule about texting today, but I wanted to say I had a fantastic time last night.”
“Should I have made you wait at least five hours for a reply?” I playfully teased back. He responded with, “Yes!”—our banter picking up effortlessly from where we’d left off the night before. My heart lightened as we agreed that we could discard the usual dating games and just be ourselves.
In the end, we both chose to move forward without the burden of traditional dating rules. That very first date turned into something surprisingly refreshing, and despite my ignorance about golf, I was excited about what was to come next. The writer of this adventure had spent more than two decades in creative roles in the entertainment industry, but this new chapter in dating felt like the most significant script yet.