So I really am not a fan of loud venues like clubs or bars (I just feel lost in a sea of people there) and I've tried OLD only to find that I must take really shitty pictures or something and get no traction there whatsoever.

Every now and again when I'm out I'll notice girls staring at me a bit or when I, in my normal friendly Canadian way, just go to say hi they seem more interested than what I'd say is normal/average. How do I go about changing general small-talk into a more deeper connection or maybe try and see if they want to hang out right there on the spot?

I mean to be clear, if all she wants is quick friendly small-talk, I'm not looking for steps/ideas on how to drag out a convo longer than it needs to go or to make anyone uncomfortable, I just want to know how to be able to gauge when I feel they might want more, what to do in those instances to see if my hunch is right.

Every now and then I've gotten the sense as things close off and we say goodbye that they were hoping I'd have had more to say. But yeah I have no idea what more I could say to keep things going with someone I just met that wouldn't come off weird (I'm good at friendly small talk but this side of my life has always just felt challenging/intimidating so idk I guess I've just always accepted they might not be into me that way and I quickly back off before I get close to having to be rejected because yeah that feels like it would suck).

Idk I guess I'm new to this and I just worry about coming off needy, desperate and/or creepy. Idk why but it's like my biggest fear that without even trying I'll be all three of these things or worse lol so any help would be appreciated.

Like what kinda things make for a good first interaction. One time I asked I remember someone said to ask questions about them because everyone likes talking about themselves but half the time I end up sounding like I'm interviewing them and I just feel weird so yeah idk at all what I'm doing lol