adventures in bad decision making and/or stepping outside of my comfort zone

This week, tuesday night I think, I joined an online dating site totally against my better judgment out of a combination of curiosity and a genuine interest in finding some people somewhere on earth who do not and never have worked at whole foods, and do not know nor have slept with any of my friends. I made a profile and someone emailed me right away, and I messaged him back, but then got distracted by something else I was doing, and and let that conversation trail off.
On wednesday night what I was planning on doing didn't work out, (it's a bit of another story, but I was doing tuesday night and what I meant to be doing wednesday night-I'll try to get back to that at the end) so I emailed the guy from the previous night out of boredom and frustration with something else who decided after iming for about five minutes that he wanted to drive to my house from two hours away at 2am, which for some reason (I'm going to stop right that now-please feel free to insert "for some reason" in any part of the story as you see fit, my reasoning here is frequently unclear, even to me) I agreed to, then he stayed at my apartment through the next afternoon at which point I agreed to go to northern vermont to the top of a mountain with a complete stranger (bad decision making) and we did go to vermont to his friends' cabin (which in reality was this giant insane house in some ski resort for the ultra rich) and then I came home on friday and somehow managed to not be kidnapped or murdered.
(high point of the whole experience: outdoor hot tub at midnight in the snow)
(I texted two friends on the way to vermont and they were both like "why. are. you. doing. that. what. is. wrong. with. you.)
So it all worked out fine, except
1. I don't normally spent 36 hours with someone I'll probably never see again, and I don't necessarily want to see this person again, but it's not how my heart operates so I feel strange about it.
2. The entire time I felt like I was in a movie, and was playing a part, and I was definitely self editing and not being myself.
3. I just feel kind of depressed about the whole thing....one one hand I was trying to step outside of my comfort zone and take chances, but on the other hand, it made me tired, a bit, and I cannot say enough times how I was not being myself.
Most of the 36 hours this was going on I felt pretty neutral about the random internet guy himself, like I wasn't sure if I thought he was cute, or if we had enough in common, and I was pretty ok with him leaving at anytime, but I thought the experience itself was good for me, because I was spending time with someone new and it was distracting me from some other stuff I'd been worrying about, and vermont really was fun, and was an experience that I wouldn't have got to have otherwise
(standing in the snow in my underwear completely warm with my hair frozen and steam blowing everywhere)
but I was still kind of distanced the whole time but then when he left I felt sad.
But do I really want that guy back, or was it just the company I liked?
(the other thing, that I was doing tuesday and wanted to do wednesday, is this whole other story that involves these semi-romantic letters with this old friend. How I feel about those letters is a whole other complication in my heart.)
Another good thing about the whole experience: at one point (actually in the hot tub in the snow which would be a good scene if my life were indeed a movie) internet guy said, "you're very beautiful and you're smart and funny, and you don't put yourself out there as if you know this at all."
True. Something to think about.