I can't tell if a coworker likes me or not. She and I both recently went through divorces within the last year for her and the last year and a half for me. She's 34 and I'm 33. I'm her bosses boss. A year and a half ago she got my personal number because my work phone didn't have service and she kept it and began to invite me to eat with her when she was in town. I made sure that she wanted me to eat with her and I explained because I am her bosses boss I didn't want to make her feel forced. She lives about three hours from me. She would come to my town and we would have dinner or lunch and when I was in her town we'd do the same thing. We would talk about divorce and how hard it was for us both. She also knew my ex wife as my ex wife was a co worker on her team. My ex wife got fired for cheating on me with her bosses boss and that's why we divorced. She would say how she thought my ex wife is horrible. When we would would go out to eat, I would pay sometimes and sometimes she would pay for both of our food. After a few months of going out to eat, I asked her if she wanted to kiss and she said no because she didn't want to get in trouble and that she wasn't ready because of her divorce. We didn't speak for a few weeks after that. This was May of 2025.
We have hung out alone after that a handful of times, but more recently, we only have been with other coworkers when we see each other. We still see each other at work events. Recently about a month ago she got a promotion to another department, and her and I were talking about it and she asked me how I felt about not being her boss anymore, and that her and I could go out for reals. I said we would see. She hasn't officially started in the new role, but will within a week of this post. We then only hung out with other coworkers. A few weeks after that we were having dinner in my town with other coworkers and she asked me whether or not I would date outside my own culture. She herself is Mexican. I said I would be open to it. She said I should date a Mexican. She also asked me if I had to be with someone that wanted kids, as I know she already has kids. I told her if I am with someone that doesn't want kids thats ok. During this dinner, she also began to talk about how horrible my ex wife was as a coworker. She also talked about going to a concert with her friend who is a girl and once again said she was single and wasn't seeing anyone.
We recently had the chance to hang out just us in her town as it was her last day in my department, but she instead invited another coworker to be with us. When one of our other coworkers suggested her and I can go out now that I wasn't her boss, she didn't say anything and stayed quiet.We then discussed the rumors of us dating from last year and she said we were both single adults so it wasn't a big deal. I jokingly said it was more fun when I went out with her as her boss. She said she would keep that in mind, and seemed kind of irritated by my joke.
I really do want to ask her out but I am unsure if she wants to or not. How should I handle this?