I'd pick the second one. It would encourage me to keep trying new and exciting stuff, make the most of my life. It'd be cool to know which aspects of my life people find the most relatable and which not so much as well. I also believe that I'd have a pretty interesting cast of characters (people I interact with often), but wouldn't we all? Lol.
[hr]
A five-day vacation,
at your dream location with your dream itinerary, but you have to spend it with a mere acquaintance
or
of a quality significantly lower than your personal standards, but you get to spend it with the person you're closest to?