Adventure: sailing Rocinante on Thanksgiving…
The thing about Thanksgiving is that everyone has somewhere to be. And that, if you play it right, makes it the perfect day to be absolutely fucking nowhere.
San Diego. Her family’s place. Turkey and stuffing and all those warm, promises of belonging. She’d asked me three weeks ago, casual. “So, Thanksgiving. I’m going down to my fathers’. In San Diego. You could… I mean, if you want to come, you’re welcome.”
You’re welcome. Not “I want you there.” Not “come with me.” You’re welcome. Like I’m a coworker who might not have plans. Like she’s checking a box.
The timing’s shit, is the thing. We’ve been dating, three months? Four? Long enough that ignoring Thanksgiving would’ve been weird. Not long enough that Thanksgiving together was obvious. We hit that threshold right as the holidays started bearing down, and suddenly we’re both doing this awkward dance of “what are we” meets “what do we do about Thursday.”
Maybe she wanted me there. Maybe she was just doing what you do when you’re in that murky territory between casual and something else, and the calendar forces your hand. Maybe her dad asked if she was seeing anyone, and she said yes, and her dad said well bring him, and now here we are, both wondering if this is too much too soon but neither of us willing to say it.
Which is exactly why I’m here, alone, on a thirty-two-foot sloop in the middle of the goddamn Bay.
The city’s empty. Everyone’s inside, fulfilling obligations and calling them traditions. The bridge hangs there in the distance, rust-red against the grey, as uncommitted as I am. The water’s cold. The wind’s picking up. And I am, for better or worse, choosing honest solitude over polite uncertainty.
Because what’s worse than being alone on Thanksgiving? Being at someone’s family table, wondering if you’re supposed to be there. Making small talk with her dad while you both wonder if you’ll even know each other’s names in six months. Smiling for the brother. Playing house before you know if there’s a house to play in.
The sails snap and fill. The boat heels. And I’m doing what I always do, choosing the clean loneliness over the complicated warmth.
She texted this morning. Early. “Have a great day.” Not “wish you were here.” Not “you’re missing out.” Just… have a great day. Like she gets it. Or like she’s relieved. Hard to tell the difference when you’re both being so fucking polite about everything.
Maybe she’s sitting at that table right now, perfectly happy I’m not there. One less thing to explain. One less person to worry about. No awkward introductions to a guy who might not stick around. Or maybe she’s hurt. Maybe she’s wondering what kind of asshole picks a boat and a dog over her family, over her. Maybe this is the moment she decides I’m not worth the trouble.
The sun’s getting lower. The wind’s getting colder. And somewhere in San Diego, there’s a woman who deserves someone who doesn’t overthink everything. Who just shows up. Who doesn’t turn a simple holiday invitation into an existential crisis on a sailboat.
But she’s also the woman who said “you’re welcome” instead of “please come,” and maybe that means she gets it too. Maybe we’re both not quite ready. Maybe the timing really is just shit, and we’re both out here, her at her father’s table, me on this boat, doing the best we can with a situation neither of us knows how to navigate.
I point the bow toward the Berkeley marina. The day’s almost over. The holiday’s almost done.
Tonight we’ll talk, we talk every night..
One more day alone. Then we’ll see.

What is that feeling when you’re driving away from people and they recede on the plain till you see their specks dispersing? – it’s the too-huge world vaulting us, and it’s good-bye. But we lean forward to the next crazy venture beneath the skies.
Jack Kerouac, On the Road