Love the idea for one person to propose an activity in hopes someone will join them, actually would be just fine for platonic or romantic outcomes, but doesn't have to start with that expectation. If someone I would never ask on a date wants to go play chess in the park with me that's probably still going to be a fun afternoon.

Also, I had a better-than-expected experience at the Bikini Hostel in Miami Beach. While there were decidedly fewer bikini clad women than depicted on their website, it was apparent that the patio was used as the neighborhood hangout. Table tennis, Picnic tables, and food being cooked on the grill every night, cigarettes and alcohol shared freely. It didn't matter if you were actually booked into the adjacent building. Many of the guys were construction workers from Argentina, once a guy mentioned he didn't get paid on time so he would sleep on the beach until he could afford a bed again, but there was a share of digital nomads too (god, can we get a different term?). Really walkable neighborhood too, nice spot. Wish they would fix up the kitchen tho.

Sounds cool, I've been thinking of heading somewhere sunny soon. Was thinking either Miami or Puerto Rico. I'll check it out.

The city of Miami itself was dull from the few miles I drove through it, searching for "Little Havana" or a decent waterfront. Miami Beach is much more of a vacation town, endless food and entertainment options, but it's expensive, I mean manhattan prices, really.

Puerto Rico is probably just as beatiful and your dollar will go farther, it was actually my first choice but a little harder to drive to ;)

yeah I'm leaning towards Puerto Rico. I think I'm going to like San Juan. That hostel sounds cool, but I also kinda like the idea of a resort experience, which is much cheaper in PR than in Miami/beach afaik.