I'm terrible with women. I was extremely shy most of my life and I've always been insanely passive around women. I'm actually a virgin, despite having a lot of opportunities at sex, due to my passiveness. I need serious help with my current situation:
I've been hanging out with this girl recently who says she still has some feelings for her ex and just wants friends for now. Twice now she has hit me up and asked if she could come hang out, both very late like 12:00 and 1 am. And yes she ended up spending the night both times which I'm assuming was her intention beforehand. We did not have sex but we did spoon and wrestle. Due to my passiveness I didn't really make a move aside from grabbing her ass. We've been hanging out for a few weeks now and I haven't even kissed her. I was actually denied the only time I tried.
Am I being an idiot here for not making a move? If a woman wants to come over and spend the night does she for sure want sex? Should I just grab a titty next time, if there is a next time? Anyone have any advice??
Before my girlfriend and I started dating we'd hang out all the time and I would spend the night. I worked with her so we'd go back to her place and get baked. She would let me stay the night and I would. She would only let me kiss her though, not even get her bra off. Every time I tried to go down her pants she would stop me.
Turns out she was testing me. She wanted to see if I would just stop coming over because she wasn't putting out. I kind of got fed up with at the time and stopped going over and spending the night. That's when she started getting guys to "pick her up after work" (only if I was working).
In my opinion, it sounds like she is testing you too. Yeah, I would say go for it. Start with drawing on her back, then maybe kiss her neck. If you really like this girl, do that for a bit and see how it progresses. Maybe she really likes you too, and she wants to see if you're a good guy (or just a horn ball).
If that fails, go get wasted with her and fuck her brains out.