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I have three maps spread out on my living room floor right now. One is digital, open on my laptop, and the other two are vintage paper maps I found at a flea market. I’m trying to convince her that a three-hour detour to see a specific mid-century modern chapel is worth it, and she is gently reminding me that we need to actually arrive at the cabin before sunset.
It’s a negotiation, but it’s the kind I actually enjoy.
I used to dread planning dates. In my previous life—let's call it the "Swipe Era"—planning was just another performance. I’d try to impress someone I barely knew, booking tables at loud restaurants where we couldn’t hear each other, or pretending to be interested in hiking when I really just wanted to talk about brutalist architecture. It felt like I was constantly auditioning for a role I didn’t want. The connections were thin, usually fading out after the second date because we didn't have a shared language.
That changed when I decided to shift my focus. I was tired of the algorithmic chaos and wanted something that felt a bit more deliberate. That’s when I ended up on latidate.com. I wasn't expecting much, honestly—maybe just a different crowd—but the rhythm there was surprisingly calm. It didn't feel like a slot machine; it felt like a gallery where you could actually stop and look at the paintings.
That’s where I found someone who didn't just tolerate my obsession with aesthetics; she had her own specific tastes that challenged mine. When we started talking, we didn't do the usual "hey, what's up" dance. She sent me a photo of a messy oil painting she was working on and asked for a critique.
Now, fast forward a few months, and we are planning this weekend getaway. It’s not perfect. I’m nervous about driving her stick-shift car, and we still haven't decided who is responsible for the coffee beans (a critical issue). But the friction is real and grounded.
We aren't trying to create a movie scene. We are just two people trying to merge our very specific worlds for forty-eight hours. She wants to stop at a local textile workshop she found online; I want to photograph a bridge. We decided to do both, even if it means we eat a late dinner of gas station snacks because we lost track of time.
There is something incredibly comforting about planning a trip with someone who understands that the journey is about the visuals, the textures, and the conversation, not just the destination. I’m looking at the route on the screen, tracing the line with my finger, and for the first time in years, I’m not worried about whether I’m impressive enough. I’m just excited to see what she points out the car window.
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