Not the friendzone but mixed signals. Thoughts? Advice?

So I [29M] recently had drinks with a woman [27], that I used to work with. I like her but I'm not sure where she stands with me, and not really sure what do next.

But first I need to bring up the back story. When we worked together we kinda had this Jim and Pam thing from season 1 of the office. We both would flirt with each other but then kinda of give of confusing signals because work frowned on office romance. Honestly some of the stuff could have been considered sexual harassment if it was in a different context. I'll never forget this one time she walked past me in the hallway, put one hand on my shoulder one on my back and slid her hand down my arm and glanced at me longingly before walking away.

Anyways, around that time I was leaving that job for another job, we went and grabbed drinks after work, twice. The last time she had a little bit too much to drink, demanded that I hug her before we leave and matter of factly told me we HAD to stay in touch after I left.

Well so I tried to reach out her but she never really responded very much, and I figured she wasn't interested and frustratingly moved on with my life.

I hadn't seen here in a year but I reached out to her to see how she was doing after I heard one her favorite songs on the radio and thought of her. Anyways, she mentioned we should have drinks, and we had a really good time. We ended by putting out a couple of dates when we could meet again and what to do. However, she has a tendency to be flaky and bail out, so you have to take that last part with a grain of salt.

It was weird though because prior to meeting up she had mentioned, "LMAO and I'm looking forward to seeing you!!!" and then when we were talking she said that when she sent that text, "I was trying to think of something that would make you uncomfortable". And I'm thinking in my head I'm thinking "that doesn't make me uncomfortable at all, that's exactly what I want you to be telling me, why are you saying this?".

Anyways, I do feel like we have something more than friendship but I'm not able to put my finger on exactly what it is. For whatever reason there is something that's holding her back, and I'm not sure what it is. At first I just thought it was because we worked together but now that's not the case I'm not sure what it is. I'd like to have something more with her but I'm worried if I'm too direct, I'll scare her away. Does anyone have any suggestions? Is she someone who might be hesitant to jump into a thing or am I just being a dumb guy whose the victim of someone who likes to be a flirt? I'm willing to chase after her if it's the first case, but if it's the second case, I have absolutely no interest and would just like to move on.

Submitted August 27, 2023 at 12:13AM

So I [29M] recently had drinks with a woman [27], that I used to work with. I like her but I'm not sure where she stands with me, and not really sure what do next.But first I need to bring up the back story. When we worked together we kinda had this Jim and Pam thing from season 1 of the office. We both would flirt with each other but then kinda of give of confusing signals because work frowned on office romance. Honestly some of the stuff could have been considered sexual harassment if it was in a different context. I'll never forget this one time she walked past me in the hallway, put one hand on my shoulder one on my back and slid her hand down my arm and glanced at me longingly before walking away.Anyways, around that time I was leaving that job for another job, we went and grabbed drinks after work, twice. The last time she had a little bit too much to drink, demanded that I hug her before we leave and matter of factly told me we HAD to stay in touch after I left.Well so I tried to reach out her but she never really responded very much, and I figured she wasn't interested and frustratingly moved on with my life.I hadn't seen here in a year but I reached out to her to see how she was doing after I heard one her favorite songs on the radio and thought of her. Anyways, she mentioned we should have drinks, and we had a really good time. We ended by putting out a couple of dates when we could meet again and what to do. However, she has a tendency to be flaky and bail out, so you have to take that last part with a grain of salt.It was weird though because prior to meeting up she had mentioned, "LMAO and I'm looking forward to seeing you!!!" and then when we were talking she said that when she sent that text, "I was trying to think of something that would make you uncomfortable". And I'm thinking in my head I'm thinking "that doesn't make me uncomfortable at all, that's exactly what I want you to be telling me, why are you saying this?".Anyways, I do feel like we have something more than friendship but I'm not able to put my finger on exactly what it is. For whatever reason there is something that's holding her back, and I'm not sure what it is. At first I just thought it was because we worked together but now that's not the case I'm not sure what it is. I'd like to have something more with her but I'm worried if I'm too direct, I'll scare her away. Does anyone have any suggestions? Is she someone who might be hesitant to jump into a thing or am I just being a dumb guy whose the victim of someone who likes to be a flirt? I'm willing to chase after her if it's the first case, but if it's the second case, I have absolutely no interest and would just like to move on.