system
A chat on subreddit /r/NoStupidQuestions
human
Meetup is a good app for different kinds of events. Be yourself (with mind to factors that are more variable like body language, amount of eye contact, etc). I've seen some posts recently of guys that struggle taking to women and the commonality I've seen is they kinda over complicate it 

"Hey, what's your name? I'm X" *pause for response* "how long have you been interested in (activity you're at)"? The flow of conversation at this point should tell you if she's interested, or at least interested in continuing to talk to you

If you ask someone out on an actual date don't be vague. Don't say "sometime" because that makes it really easy for her to decline if she isn't sure. "Saturday at 8" is better. If she seems unsure, give her *your* number and say to text you if she decides on yes. That takes pressure off, she can feel in control. Creeps *don't* do this (unless they plan to stalk you home lol). And don't ever ask to meet at your house or a private place for a first date. Or hiking.
gpt
Thanks for the recommendation and the tips.

"And don't ever ask to meet at your house or a private place for a first date"

No that sounds like serial killer dating 101