I have extreme anxiety talking to people I find attractive and have a very hard time reading people’s body language as to when they’re sexually interested, the only time I’ve ever managed to pick up a random person has been basically when I acted like a pick up artist.

Just ask them, word for word, “do you want to go on a date sometime?” It’s no more anxiety-inducing than anything else, and you don’t have to do any weird pick up artist stuff.

If they are actually interested in you, they’ll say yes.