God, Catfish, and a Woman Who Wanted a Hookup

So, here’s the thing. I went to Mass this morning—it’s Good Friday, a Holy Day of Obligation, and while I may be floating through life a little more freely than most, I still like to anchor my soul now and then. There’s something about sitting in the pew on Good Friday, listening to the Passion reading from John’s Gospel, that hits different.

The honesty. The betrayal. The quiet strength. The raw humanity of it all.

Jesus didn’t fake anything. No filters. No flattering angles. No edited profile pic from 2008. Just pure, sacrificial love—flawed humans and all. Which, funny enough, got me thinking about dating.

(Stay with me.)

After Mass, I did what I always do—I headed to “Just Deserts” for my 5 shot, extra hot no foam skim late, to smell their pastries, and do a little “boredom logging” (what my blogs are all about…writing the thought in my head to help kill all the alone time I have.) That’s when I started writing this.

Let’s face it—being a man in the modern dating world is weird. And no, not in the “I still live in my mom’s basement and collect samurai swords” kind of weird (though I do appreciate a sharp blade—just not metaphorically from someone’s last relationship).

Apparently, expressing your feelings and being emotionally open as a man is… intriguing. At least that’s what I’ve gathered from the raised eyebrows and, “Wow, you’re really in touch with your emotions,” comments I’ve gotten. Newsflash: I’m not weeping into my wine every night—I just know the difference between a feeling and a foot cramp. And yes, I talk about them!

What’s interesting is that a lot of the “mom” readers of this blog are curious—maybe even fascinated—by what a guy goes through trying to date in this brave new world of swipes, winks, and algorithms. Especially when you’re not just looking for a date… but for someone who’d never dream of being on a site like Match.

See the problem?

The woman I’m searching for is probably somewhere out there being classy and quiet—reading real books, sipping something other than boxed wine, unaware she’s my soulmate and completely uninterested in profile-picking through the online bargain bin of humanity. Meanwhile, I’m on these sites trying to find the one who slipped past the bouncer.

And look, it’s not like I’m being picky. I’ve tried. I’ve really tried. Years ago, I set up a date with a woman I met on Match. I even brought my friends Andy and Sharon to casually scope her out at the bar. They had seen her picture and knew what I thought I’d be meeting.

Bless their hearts—they were speechless.

The woman who greeted me was, generously speaking, two hundred pounds heavier and ten years older than her profile photo. I don’t mean “oh she gained a few pandemic pounds” heavier. I mean if I had brought a life jacket for her, it would’ve begged for backup.

And just when I thought the night couldn’t get more awkward, I walked her to her car (because I’m still a gentleman, knowing everyone is trying their best to meet that special someone - even when I feel catfished), and she looked at me with all the subtlety of a billboard sign and said, “I know you’re not going to call me… but would you be open to just a hookup?”

Yeah.

No, ma’am.

Hard pass.

So, if you’re wondering why I’m now advertising myself like a floating romantic job posting, it’s because I’ve earned that right. I figure, why not skip the swiping and go straight to the source? I’ve already got a QR code on the side of my catamaran, Ohana, that had linked to the charter site I had. I could turn that into a page that says, “Adventurous, emotionally fluent, slightly sarcastic man seeks First Mate with good sea legs and better intentions.”

Because the kind of woman I’m looking for? She’s probably not browsing dating sites. She’s probably not replying to random DMs. But maybe—just maybe—she’s sipping coffee on a dock, sees my boat, scans the code, and thinks: Huh. This guy seems interesting. Maybe I’ll take a chance.

And if not? Well, I might just start my own dating site:

“Sails & Souls – For Those Who’d Rather Float Than Swipe.”

Interviews take place this summer on deck. Resumés optional. Sunscreen encouraged.

So with that said:

Single? Tried those internet dating sites? Age 40-55? Interested in setting sail on more than just a metaphor?

This summer, Ohana will be cruising the Chesapeake—anchoring in quiet coves, chasing sunsets, sipping good wine, and seeing if sparks fly under the stars. I’m inviting one remarkable woman (or maybe two for a trial run—calm down, it’s not that kind of boat) to join me for a leg of the journey. No, it’s not The Bachelor on water—just an honest guy, looking for real connection, quiet mornings, loud laughter, and something that lasts longer than a swipe.

Think you’ve got the spirit, the strength, and the sass?

There’s a QR code on the hull. You’ll know what to do when you see it.