By the title I really just mean doing anything in hope to escalate things romantically with a girl You have a crush on, here's my current example.

°skip this paragraph if You want, it's just my current example° A while ago I was on a vacation with a friend group, and in that vacation in particular I was the fun one and the one who would decide and so forth (I played my cards right and really came across as my best self) (we're all high school students) and since we were in a hotel i would always pick the same spot and she would always pick the spot in front of mine (so i really can't tell whether it was force of habit or her being into me somehow), we also played games taht involved physical contact and for one of them we decided to pretend we were just random people (it was some sort of hyde and seek) and in order to do that We ended up holding hands, and I got other "signals"

The thing is I started getting into her because I thought She was into me, so I was wondering if in general confessing your feelings to your crush/flirting is a good idea or You have to start with girls/women who you know are already into you. So far I've only had luck with girls that seemed interested in me and that seemed interesting to me, and that I simply "pursued", but then again I've never "confessed my feelings" to a crush.

More info: (again, specifically for this one case) -no, We're not friends, I already knew some of her brothers/cousins but with with her the risk of "having friendzoned myself" isn't there -in order to try and make my interest clear I even texted her goodnight at like 1am this one time we were texting and She hit me the next day with a "good morning"