Two Women, One Boat, and My Goofy Self Trying to Decide

Alright, folks, gather 'round for another episode of "What in the Nautical Nonsense is Happening in My Life?" Because apparently, the universe thinks it's hilarious to throw me into situations where I have to make actual decisions. Sigh.

So, remember "Ohana Lisa"? Yeah, haven’t heard much from her lately. I mean, I get it—she’s busy renting out her house, moving to Annapolis to start crewing on a boat, and, you know, working. But she’s also been less than enthusiastic about hopping on a FaceTime call, which has me wondering… am I being ghosted, is she just playing hard to get, or does she just have no interest in meeting a man? (Or—plot twist—she’s actually busy like she says? Nah, that can’t be it.)

Meanwhile, as I twiddle my thumbs and overanalyze my social life like a teenage girl before prom, another beautiful woman appears on my horizon. Her name is "Lee," and get this—she’s 11 years younger than me. Now, I know what you’re thinking: “Wow, good for you!” But also, I’m thinking: “Oh boy, can this old fart keep up with her?” But hey, I’ll cross that rickety bridge when I get there.

Not only is Lee younger, but she’s also Chinese and absolutely exotic—and I don’t just mean her background. She’s tiny. Like, perfectly fit-in-small-boaty-nooks-and-crannies tiny. Imagine the absolute convenience of having someone who can actually reach under the port flooring to clean the AC saltwater strainer without cursing the gods of boat maintenance! This is next-level practical attraction, people.

Of course, life isn’t all about squeezing into tight spaces (despite what yoga teachers try to tell us). She was married for 25 years, which sadly ended, and she’s dabbled in dating since. Her last boyfriend wanted an “open relationship” because, apparently, some men just love making dating unnecessarily complicated. (Ladies, I see you. We men don’t have a monopoly on dealing with absolute nutcases.)

And honestly? I’m starting to lean more toward Lee than Lisa. Coming from such different backgrounds, it feels like a refreshing change—one that will give us so much to share and learn from each other. As I’ve always said, I’m not looking for a match but rather someone who complements me, and Lee seems to bring that balance in a way that excites me.

So here I am, weighing my options. Two amazing women. One decision. Zero escape routes.

Ohana Lisa is experienced with boats and completely hands-on. I mean, she could probably tie a bowline knot in her sleep, blindfolded, while giving a TED Talk about it. But that doesn’t mean Lee can’t learn! After all, sailing is like life—it’s not about where you start, it’s about how well you can roll with the waves (and whether you’re willing to stick around when things get choppy).

Now, being the upstanding gentleman that I am (cue laughter), I plan to be completely open and honest with both women. No funny business, no leading people on. Just a good old-fashioned, grown-up decision about who I want to set sail into the sunset with. And let’s be real—whoever I let down will probably be secretly relieved they escaped the craziness in my head.

But let’s be honest—for all I know, I won’t have either by the time I get back to Annapolis. This rollercoaster ride I’m on, trying to find my next first mate, might just throw me right off the rails before I even leave the dock and both will want nothing to do with me!

So, stay tuned. This boat’s about to set sail, but with who? Even I don’t know yet. But one thing’s for sure: the sea of romance is as unpredictable as the wind, and I’m just out here, adjusting my sails, hoping I don’t capsize in the process.