So I'm a little over a year divorced and still struggling with assertiveness getting back into the game. I did have a live-in relationship since the divorce with a slut who threw herself on my dick (terrible decision) but the fact is, I haven't been assertive with women in YEARS. And even when I was more active, all of my relationships have been with women who were proactive in letting me know their attraction.

Here's my dilemma. I have been hanging out lately with this chick that I've known for a few years. She's pretty cool and we click as friends, though as you can imagine neither one of us are getting much out of the friendship. We have recently been chilling more and I'm pretty certain that she is DTF. However she is extremely vague and doesn't give me much to work with. The most she usually shows are little ambiguous IOIs like flipping her earrings, etc.

This may sound like an obvious signal but last night she shifted her position on the couch so that she was laying on her stomach facing me with cleavage showing. However she was still about 2 feet away and I couldn't imagine any escalation scenario that wouldn't be extremely awkward. Another source of anxiety for me in the whole situation is the fact that I don't want a relationship - it is completely against my wiring to pursue a girl that I don't actually want to commit to.

I'm not here to argue about red flags or female friendship. I am NOT interested in a relationship with her and am not going to let myself get used, past a certain point at least. We're hard wired to enjoy helping women after all.. I just need advice about how to break the 3ft thick ice that's been building up for years.

I finished writing but just had another realization. I had a lunch date with an old friend recently and I think she was IOI-ing me as well. Touching my arm when we talked, etc. I defaulted to beta mode and it all zinged off of my nice-guy armor. Back in the day she was like a god that I fruitlessly orbited and I treated her as way out of my league. Very pretty girl. I honestly may have more of a chance with that hottie than the previously mentioned girl as my recent failure count is much lower and I was somewhat IDGAF on our lunch date.

Anyways this is getting much longer than originally intended. I just remembered another interaction from like 6 months ago where a girl was actively trying to dance with me and I completely froze up. I'm realizing that I have zero escalation game whatsoever, maybe even in the negative digits. Extremely low self-worth, perhaps?

Any thoughts are appreciated, thanks.