So, I'm 25 and this is my situation: I am finally "out" of a period of struggle in which I took time to work on myself and my own life. I went through a very bad breakup about 15 months ago with my gf of 15 months or so. She was one of two girls I've dated LTR, and I hooked up with a few others in college.

After the breakup, and because of other struggles going on in my life, I went through some low mental times. Nothing serious (no drug or alcohol use), but just feeling really down and dejected about life for a good year or so. I deliberately chose to not pursue anything with anyone while I focused on fixing issues in my life and strengthening myself. I mostly received interest from unattractive, desperate girls during this period, but I declined them of course.

I'm finally past that period now and I'm feeling really good again and doing better than ever. Life is busy and confidence is high. Now my biggest issue is this: I've forgotten how to escalate. It's been so long since I've been in this position (not since I got with my last gf, which was almost 3 years ago). Escalating with her was easy as hell because she was a virgin and I was naturally attractive and fun to her, so once she gave me clear IOIs, she let me take control and stuck with me even if I did or said dumb things, because we were both young.

But now it's different because most girls around me aren't virgins, so they're more specific about what they're looking for.

My looks are good and my ability to communicate is very good (I'm assertive, in control, talkative), so there are no issues there. I can talk to attractive girls completely normally about anything in life and I'm very direct. I don't like to bullshit; I am genuine and to the point.

I have some girls around me right now who I find attractive and who seem to like being around me.

I admit I'm afraid/unsure how to escalate anything sexual because of these two reasons:

1. I see them all regularly, and if they reject advances, it could make things awkward and I am not used to having to deal with awkwardness.
2. Girls gossip like crazy and will go tell everyone that I did/said something wrong AND/OR false allegations of harassment

If someone could point me to a simple, straightforward guide to escalation, it would really help me a lot. I need to have a plan going into things. I can't just improvise and bullshit it or I will make a mess of things. Thanks in advance.