I don't know if this is rational, but ever since #MeToo came out and all these allegations of harassment and rape and what not, I'm afraid to even approach a woman. For example, I have a younger coworker, who i think is adorable and sweet. She's a bit younger, and even the other day put her arm around me. She was always quiet until she met me and jokes around with me and opened up a bit. But I can't even bring myself to ask her out on a date because it's my coworker...and the harassment claims scare the shit out of me. Also the idea of a woman playing hard to get vs. No Means No...this has been all very confusing, as I wasn't great with the girls to begin with.

Don’t be scared as long as you are polite and respectful ask her out there is no reason she is going to think you are harassing her. Plus from what you say this girl like you so I’m sure she is going to jump on to you when you ask her out
Don’t wait too much or somebody else will win her over you.
I’m not much on this forum anymore hope I could help you a little