So last week, I was at a friend's, and on a whim asked a woman out who was there. We had a successful enough first date, I guess... which is weird. I had a good time, but didn't feel any connection, so I didn't even bother lining up a second date, I figured "we both had fun, let's just part ways".

Well she follows up basically asking me out for a second date this weekend, I figure sure, why not. My buddy was saying that's like exactly the right attitude to have, and was suggesting I "take advantage of that momentum" and start asking out more chicks, and starting some online profiles like... Hinge or something, I think?

Now here's the thing: I'm all for asking more women out. I actually feel like I'm in a good place in life, with who I am. But I also know my strengths and weaknesses; and a big weakness is that, honestly, I'm on the "ugly" side. It is what it is; no point being insecure about it. But I also know that shit doesn't cut it for online dating.

What would you recommend are good opportunities to ask random women out? With covid going on, the chances of meeting people "at parties" is lower than ever (I only met this woman because my friend invited me to Thanksgiving). It's also cold as shit outside, which is a bummer.

One thing I've noticed is that a lot of gorgeous women seem to be going grocery shopping in the early-afternoons. Maybe this is news to some of you guys, or maybe not, but I've definitely noticed women getting done up before heading to shit like "Trader Joe's" and places like that. So... maybe women are a little more open to cold-approaches than normal?

I dunno. I'm definitely open to changing my daily routine up a bit, though, if there places I should start "swinging by" regularly? I've never been much for bars (since unless I'm meeting friends, I never have a good time) although hell, maybe I should change that too?

Also, I'll throw this out there as well: I play guitar okay. I enjoy playing, though I'm certainly not going to be serenading anyone. I used to enjoy playing outside my office during lunch break when it was warmer. Maybe I should bring my guitar more places to play? But how to do so, without looking like you're "trying to impress people"? Or just say "fuck it" and do it anyway?