So, my best friend (f) and I (m) are very close. (Yes, that old chestnut.) We’ve made out in the prehistoric past (it’s complicated), but we still flirt casually from time to time all these years later. There’s a connection there, even if it’s not romantic. We’re both in our very late 30s, currently single, etc.

Once a week, our rotas match and we walk into work together. I live 5 minutes away, so she parks outside mine and meets me at the end of the road.

For recent context: I have been away, so it’s been a little while. And as I stepped outside to greet her the other day, she smiled at me in acknowledgment, and immediately starting staring intently at my groin as I made my way forward. Perverts are not that obvious and her look is forever burnt into my mind. My point is, it was not subtle at all, and kind of adorable watching her catch herself and look away blushing. In any case, I simply enjoyed the moment and chose not to tease her about it at the time.

(In my experience, women are rarely that obvious, especially her — and I spent the day double-checking my fly and wondering if there was anything noticeably visible down there.)

So my question to you all is: Does she like me?

I kid. Obviously, I’m going to talk to her at some point. We’re both emotionally intelligent people — and I don’t necessarily need more out of our relationship; I’m not going to confess my love or anything. But she’s been signalling (more subtle) interest at me for a while, and I don’t know how to tell her I’m interested in kissing her neck as well…

Or have I just answered my own question?! (“Talk to the woman.”)

But keeping with the rules of the subreddit:

How would you escalate things with an attractive female friend that’s (kind of) asking for it?

…or in more broader terms:

How would you approach somebody shy that’s showing interest?

Thanks for the tips!

(She’s the kind of person that needs me to make the first move. But I don’t want to come on too strong.)