I'd like to add a note about the hired gun/waitress.
They're a tough nut to crack. You shouldn't have gone to that same bar the next night, especially by yourself. See, it's hard because you don't want to appear so available. Women see it as desperate, or "creepy" (God, I HATE that shaming word). However, you need to occasionally show your face and flirt during those occasions. It's a fine balancing act, and imo, is not worth the effort. Most of the time you end up looking like every other chump. Use your time/energy elsewhere.
Also, props on getting out of your comfort zone.
They're a tough nut to crack. You shouldn't have gone to that same bar the next night, especially by yourself. See, it's hard because you don't want to appear so available. Women see it as desperate, or "creepy" (God, I HATE that shaming word). However, you need to occasionally show your face and flirt during those occasions. It's a fine balancing act, and imo, is not worth the effort. Most of the time you end up looking like every other chump. Use your time/energy elsewhere.
Also, props on getting out of your comfort zone.
Fortune favors the bold.