This is something that I think I need to start doing but I'm not sure.

A few months ago I was hanging out with a coworker. The second time we hung out was swimming at the river and I was very touchy with her, rubbing her legs, hugging her in the water etc. When we got back to my place at night I tried to kiss her she said no and that I was drunk. Whatever, it was just the first try.

A few weeks later we went to downtown and again we got drunk. I was very touchy with her and she playfully hit me a few times. She expressed not wanting to stay at my place so we ended up walking for almost 30 minutes before we got an Uber so she could sober up more. When we got back to my place I tried to do a standing hug and kiss thing and she resisted so I backed off. Then we sat on my couch I had my arm around her shoulder and we just talked till she felt like she could drive home. When she got back home we texted for a bit and I was joking that if she stayed at my place she would be kicking me in bed.

For all I was concerned I was very direct with my interest. And yet she hung out with me many more times from then on. For some reason I didn't try to kiss her again, probably because I was so focused on having sex with her I didn't see a kiss as something separate. Funny that I just thought of that now. Hah that's interesting.

Anyways, she kept agreeing to hangout with me even though I'm sure I made it obvious that I wanted to sleep with her. So my line of thinking now is that I didn't try hard enough to make her react. I feel that I should have kept trying when she was at my point till she gave in LMR or that she left out of anger and never wanted to see me again. At least that way I would know for certain that there was no chance. Or maybe I should have just tried to go for a kiss the next time we hung out and not worry if could we couldn't have sex right then.