When I was in college way-back-when, I lived in an apartment about a 1 minute walk way from a bar - the bar that would become my college watering hole. My first time going there, I got the number of an absolute smokeshow of a bartender. We made plans to get a drink one night, but the day of, I just got way too drunk during the day and was in no condition to do anything that evening. So nothing happened with her.
Over the next few months I brought a maybe 5-6 girls to that same bar. It was my go-to place to bring girl, and friends in general. Great service, great atmosphere, quiet enough that we could talk, etc. A lot of the time, it'd be that exact same girl who would serve us. I could tell she was a bit jealous and often times completely ignored the girl I was sitting with while getting orders. She'd look me dead in the eye and not even glace over at the girl.
When I went there with guy friends, I noticed she stuck around my table a bit to talk, and also when I went up to the bar to get a drink (and she served me), she pretty much did the same thing - she wouldn't ever just give me a drink and that'd be that. She always said at least a little something, however harmless.
I never ended up texting her again until a few months later, I got a bit curious about her and decided to antagonize her a bit with a text:
[Paraphrased; college was years ago]:
Me: "It's $1 beers tomorrow right?"
Dead silence for like half an hour
Her: "Who's the lucky girl?"
Her: "What do all these girls see in you?"
Me: "You wanna find out?"
The next day she had off she was in my bed. I could have made small talk, been somewhat of a beta and struck up a long conversation about dating and life or whatever else which is a mistake I think a lot of guys make, but I just figured that since I had social proof (jealousy is the ultimate aphrodisiac for women), and since she was jealous, saw me with other (good-looking) girls, and knew that I had other options, I figured the odds were in my favour.
I figured I didn't really need to make things too difficult for myself. I got straight to the point. Even if she had said no, at least I didn't waste a bunch of time. Better to get a no in 5 minutes than in 5 months.