I’m in a tough spot with a friend who is now my boss. Should I confront her or avoid?

Just to preface it, I feel like a teenager again with the way I feel and act around her. This is real and I’ll looking for genuine help. What is she thinking? Full story below

4 years ago, I (29m now) was married and she (Ashley, 28f now) was in a committed relationship. We met at work and clicked. We joke around a lot and have grown closer, enjoying each other’s company (or so I think). She sometimes makes it an effort to come sit with me or talk to me. Mostly I would be the one to initiate these things, but so would she. We were a group of 3: me, her, and this girl (Riley). Sometimes we would hang out after work for dinner, movies, escape rooms, etc. When talking to her, I’d always tease her and make fun of her (in a friendly way) and she would always laugh. The majority of our “friendship” was me making her laugh, leading/supporting her work, and giving her advice when she needed it. She grew closer to me and gave me compliments on my leadership skills and handling pressure multiple times.

Once we were working on a project for 2 months together. I was the lead on it, but we worked closely together. We worked weekends and averaged 12–16 hours daily. Our plan for the entire team was to meet at our office at 9am for work until 2pm, then go to the client’s office until we finish, sometimes 2–4am. Her house was closer to the client’s office, but she always carpooled with me and I dropped her back to the office at night, even when it was easier for her to just go to the client’s office and drive home after. When she would finish work at 7pm, she’d stay until I left to help or talk. Once we ended going back to the office at 3am and she was being a bit flirty (I didn’t notice it at the time).

Another time she was going to travel for a project and was a bit insistent indirectly that I go with her to help out. I did, but nothing significant happened. She dressed differently, wearing a white crop top and asking personal questions. I missed the mark here too on opening up.

In between all of this and on a few short occasions, she would tell me how her BF doesn’t give her enough attention, doesn’t hang out with her as much outside of their friend group. How sometimes he is hanging out with mutual friends and they’re playing a game, and she’ll call saying she’ll come hang out and he’ll tell her not to come because they are so focused on the game. I asked her once how they met and got together, she was vague but said her entire friend group met at university and he liked her a lot. He either asked her out and she said no or he told them and they all “convinced” her to give him a chance because he is kind and comes from a good family, etc. (She is wealthy, and so is he but not on her level.)

We both ended up leaving the company, but she left first and came back to visit once, wearing makeup, her hair done (on Valentine’s Day. Note, I’m still married and she has a long-term partner). When I saw her, we hugged, but the hug was very tight, her hands over my shoulder, and it was a long hug. We hugged for almost 10 seconds. Then we went to the company’s lounge and on the couch we all played this trivia game with the team. I said a joke and she got up laughing and then touched my hand.

I left the company, and went cold on communication for a bit, but she kept messaging me job links (she didn’t know I found another job). We ended up going out like 2 months later, the 3 of us, and continued to try to see each other multiple times as a group. Sometimes I’d try to invite her out alone, but she would raincheck and never reschedule—even when I say “yeah we can raincheck, but it’s on you to reschedule.” Anyway, she would respond to my IG stories teasing and what not, being friendly or laughing at the funny videos I post. Until this day.

I noticed that for birthdays, she wouldn’t put in effort in planning. When we did Riley’s bday twice, I did all the planning. When Riley did mine, Riley did all the planning. No effort from Ashley’s side. For my birthday I got an action figure of a character I liked (Riley picked it out) and Ashley got me a carry-on bag because I started a new job working for an airline and would travel a lot. For Ashley’s birthday—the first one after we all left—I gave her a bunch of gifts, and then I gave her a personalized letter telling her how great of a friend she was (it was lowkey a love letter, but phrased completely like “you’re a great friend blah blah”). She took it, read it, closed it and put it in her bag without saying anything at all. After that, I stopped engaging much with her. Only texted her to plan Riley’s birthday and did it.

Fast forward to her second birthday, I planned everything again. Because Riley’s birthday is exactly a month after Ashley’s—and I know Ashley never plans anything—I planned it anyway. After we did Ashley’s birthday and Riley left dinner early, Ashley asked me what should we do? I told her I already planned it and bought these gifts if you’d like to contribute. She suggested an additional gift she could buy, I said okay and to just text me when everything arrives. She never did, and we never did Riley’s birthday. I ended up doing it alone without inviting her. My birthday came around and she never wished me a happy birthday.

Once Ashley and I went out for dinner, very intimate sushi place. We stayed there for 4+ hours just talking—mostly her talking and me listening. She showed me pictures of her growing up, a new brand and business she is working on, and the story of how she found this company that built her brand for her. She was proud of it and I was listening to her very attentively. She was enjoying it a lot.

I got divorced (I know random input, but for who might ask, our relationship was dead a while back. and we were both waiting for somethings to finalize the divorce and tell our families, nothing related to this situation), and when we went out for dinner the 3 of us, I told them. Riley was empathetic, saying nice things. Ashley didn’t say much. Not much of a reaction from her. Riley said “I’m here if you need anything blah blah,” Ashley just said “yeahh we’re here.”

Now, she messaged me asking if I knew anyone open to working with her at her company for a higher position. I was looking for another opportunity so I accepted it, and we work together—she is technically my boss.

Typically I go to her office to chat, listen to her when she wants to speak or vent, or talk about her other business/passion project and I’m always an active listener. I didn’t feel the same level of effort from her, but she always accepts my compliments, mildly flirty comments, etc. Sometimes she would tease back. Sometimes we step out for coffee and she started telling me personal things: her life story, her parents, her dad and how he was sometimes hard on her, how she didn’t grow up in a very emotionally open/safe home, etc. She would sometimes mention how her BF won’t reassure her on marriage and how he won’t propose because he wants to achieve certain goals first. She opened this topic a few times, but I didn’t indulge it too much because it makes me uncomfortable. I tried to stay neutral and tell her maybe he wants to be ready financially, emotionally and physically to be responsible for a woman.

Another time we went out for breakfast during work with the entire team. We played a card game (Getting Closer: Team Edition) and a question came up: “what do you admire most about your colleagues?” Each person answered for each team member. Everyone on my team said amazing things about me like how I’m very emotionally and socially intelligent, kind, gentle, genuine. She also said the same things. The conversation turned into each person sharing a story on the kindest/most empathetic thing I’ve done for them. When we went back, she was around me most of the day. We then had a corporate event that night.

Once we were invited to a corporate event at night. Kind of like a gala but not too fancy. I offered to pick her up from home, go to the event, and drop her home and she obliged. She came drenched in perfume. We drove to the event joking a lot and laughing, enjoying music. At one point when we were laughing, we were pushing each other’s arms while laughing because it was funny. We go to the event, finish, then while we are waiting for the valet, she mentioned her BFF is getting engaged. I told her hope you’re next, she said “yeah I keep sending him pictures of rings and he only reacts with emojis of laughing. He doesn’t tell me. He promised by EOY but I don’t even know when. Just give me a timeline.” We get in the car then I suggest we order in and I can show her my place. She agreed as long as I drop her home after. We went back, I showed her my place, and stayed from 10:30pm to 1am at my apartment just chatting. I listened to her childhood and I joked around a lot and she laughed. I dropped her home after that, nothing happened. Next day her and the entire team is in my office for 1 hour eating lunch and working. She was looking at me frequently even though I’m not talking to her and she’s not really part of the work conversation.

Now I’m pulling back a bit because I feel like I’m leading this “friendship”—taking initiative, trying to talk, asking about her—but not getting the same back. For about a week, I stopped engaging, only go to her for work, and message her only about work. Note, the group of me, her and Riley has been dead for months—maybe 8–10 months. She is now sending old memories (she did this twice) in the group chat and also reels on our IG chat. She knows I like (as a friend) one of her friends Duna (I met her once, but heard great things about her from Ashley). She used to tell me sometimes “yeah we can hang out together, I’ll invite you next time” or whatever, but never does. She randomly texts me during the week I wasn’t speaking to her saying “her friend Duna had a few questions about subject (I’m an expert in) and I gave her your number if that’s okay?” It was odd and random. Felt like she was doing a temperature check.

She came to my office yesterday before heading home after me not talking to her for a while. We spoke a bit and she started telling me things like “I have an appointment at the doctor’s for blah blah,” “I started a tennis class.” I was a bit engaging, but the vibe was obviously off. When she got up to leave, we joked very lightly (she hates it when people misspell her name), so I threw in a joke about her name to tease and she laughed and gave me a look before leaving. But I know she felt something off.