At some point, I stopped trying to count how many first dates I’d had. Was it 37? 48? The number was less important than the slow realization that I was essentially speed-dating the entire middle-aged male population of the North Bay.
It was like I had unwittingly entered an endurance race, but instead of a medal at the end, I got ghosted by a guy named Gary, who called his dog his “business partner.”
I’m not new to the game—just newly single after a long-term relationship ended with the mutual realization that our love had evolved into something best described as “amicable roommate energy.”
So, I dusted off my metaphorical dating shoes (a pair of well-worn Blundstones, because, North Bay) and jumped into the deep end of the dating pool. What I discovered was that the pool is shallow, chlorinated with the tears of ex-wives, and occasionally features a rogue pool noodle that thinks it’s ready for commitment but is, in fact, just floating aimlessly.
The Apps: A Graveyard of Bio Clichés
I started with the usual suspects: Bumble, Hinge and the requisite three-day stint on Tinder, before realizing it was where hope went to die. Bumble seemed promising—if one ignored the profiles that were either entirely photos of motorcycles (are you dating, or is it just the Ducati?) or contained bios like “fluent in sarcasm” and “I’ll make you laugh—guaranteed.” The men here were very into hiking, very into IPA culture and very committed to never texting back in a timely manner.
Hinge had more of a “I’m ready for my second marriage” energy, which I admired. But there were also a lot of photos of guys standing on boats. Where are all these boats? Is there a secret marina full of midlife divorcées waiting for me to swipe right?
And, of course, there was the friend setup, which was less of a lifeline and more of a slow-motion disaster that I walked into because I am an optimist.
Date #1: The Man Who Hugged Too Long
Gary (not his real name, but if you’re out there, Gary, I hope your dog is thriving) was a setup from my well-meaning yoga friend. She described him as “a really deep thinker” and “super into spirituality.” This should have been my first clue that I was about to embark on a journey best documented for anthropological study.
We met at a vegan café in Mill Valley. He arrived wearing a linen tunic and exuding the strong scent of patchouli and aura work. He held my hand a beat too long when we met and said, “I already feel so connected to you.” I nodded politely, as one does when someone on mushrooms starts explaining quantum physics at a party.
Over matcha lattes, he shared that he lived off the grid (but had excellent WiFi, somehow), and he made his living leading “intimacy retreats” in Sonoma. (“Intimacy” being the operative word here.) When I asked what that entailed, he gazed deeply into my eyes and said, “Let’s just breathe together for a moment.”
And reader, I did. Because I am polite. And because I was still hoping for a slice of banana bread before I fled the scene. But as we sat there, eyes locked, breathing in rhythm like two synchronized swimmers in the pool of what is my life, I realized I was in the opening chapters of a woman-in-peril novel.
Ultimately, the moment ended when I fake-checked my phone and told him I had to pick up my (nonexistent) dog from the groomer.
Date #2: The Man With the Exit Strategy
Then there was Steve. Steve, I found on Hinge, and his profile gave off solid “dad who does his own taxes energy.” He had a beard (as required by North Bay ordinance), two kids in college and liked “exploring new restaurants.” Perfectly fine.
We met at a wine bar in Petaluma, and within 10 minutes, I knew two things:
1. He was very prepared for this date to be terrible.
2. He had an escape plan.
I discovered this when, midway through our charcuterie plate, he glanced at his Apple Watch and said, “Oh man, my buddy just texted me—he’s locked out of his apartment. I should probably go help him.”
I stared at him, asking, “Your buddy, a grown man, has no other way into his own apartment?”
Steve blinked and said, “Yeah, well, he, uh… lost his keys?”
I took a sip of my wine and nodded, saying, “That’s weird because I thought you were the one looking for the exit.”
To his credit, he did not try to deny it. He just shrugged and said, “You seem cool, but I have a rule about not dating women who have read more than 100 books.”
I stared at him and said, “That is… a very specific rule.”
He replied, “I dated a woman who read 200 books in a year once. It was intense.”
And that’s how I got dumped for literacy.
The Philosophical Reckoning
After these (and other) adventures, I started wondering: What exactly was I looking for? Was I actually searching for love, or was I just accumulating material for a Netflix dramedy starring Sarah Paulson? (Working title: On All Dating Apps.)
As Miranda July aptly puts it in All Fours, “You had to withstand a profound sense of wrongness if you ever wanted to get somewhere new.” Maybe I was looking for love, or maybe I was just looking for a dinner partner who could hold a conversation that didn’t involve “spiritual downloads” or escape plans.
What I do know is this: Dating at this age is less about chasing the fairy tale and more about finding someone whose weirdness complements one’s own. Someone who won’t judge your overly complicated coffee order or your encyclopedic knowledge of ’90s rom-coms. Someone who might, on a random Tuesday, say, “Hey, let’s go to that weird roadside attraction in Sebastopol,” just because it seems fun.
Until then, I’ll be over here, living my best protagonist life—awkward, hopeful and still open to whatever strange, beautiful thing comes next.
Kris Eff lives a fictional life in Petaluma.
