Major context- we've been friends/coworkers for about 3 years now with our relationship getting progressively closer from working together once in a while to doing mushrooms in a 1 on 1 setting and being pretty open/vulnerable in all sorts of conversations. We are both currently single and have both been in/out of relationships throughout our time knowing each other.
Timeline-We work together in emergency services so countless 12+ hour stressful shifts in close proximity and plenty of downtime to get to know each other when its slow. She started out part-time which meant she had the opportunity to choose each shift she worked while I was full-time and had to stay committed to a regular schedule. I'll point out she is very attractive and tons of coworkers have made and continue to make passes at her and even though I find her attractive as well I feel like I kept it respectful while getting to know her because I don't usually date coworkers anyways. We got along well from the start and she started picking up the majority of her shifts with me. Like I said before, it can be pretty easy to rack up hours of time with someone in this field especially when it's slow so after a while she suggested that we should start hanging out outside of work and we started getting a lot closer. She was kind of in and out of relationships during this time and would often keep me updated if she started seeing someone and whether or not things were going well. I pretty much always expressed my support and gave honest feedback when she asked for it. About 1.5 years into this she shared with me that she was getting harassed by another woman at work who I also happened to be close to and this threw me off. She told me that the other woman was spreading rumors about how she would sleep with anyone and is a homewrecker. I honestly didn't believe it at first because the other lady was always incredibly nice until I ran into her at work and she pulled me aside to warn me about my friend. She basically told me the same things in this ominous tone of voice that she would break my heart or just try to get into my pants. At that point I realized that she did seem to be spreading rumors and my friend ended up having to file a report with HR. I ended up getting called in and basically made my choice to support my friend even if it meant ruining the relationship with the other lady. Ultimately I wasn't the only one that came forward to share a similar experience but the majority of people who got called in were genuinely afraid of retaliation because everyone knew that the one spreading rumors had pull with management and was kind of a company favorite. Needless to say that lady hates my guts now and absolutely mugs me anytime we cross paths but I still feel like I did the right thing.
After that investigation I ended up going on a long vacation and came back feeling like I was ready to start dating again. I ended up using some dating apps and was about to stop when I met someone in her early 20s who was pretty intriguing. I wont lie, at this point I felt like I was in between pursuing my friend or continuing to date the younger woman. A lot of my friends told me I should pursue the friend because she had more life experience and we already had a lot of chemistry or history together. Of course during this time I kept my friend in the loop that I was starting to date and she gave a lot of good and honest feedback/support, expressed a lot of happiness that I was doing well. I continued to date the younger woman and our friendship continued over the next year and a half or so.
Why I think she might be into me-
Even before having her back during the investigation we were quite playful with each other and flirting was common between us whether at work or when hanging out. More often than not she was the one asking me to hang out and would frequently express missing me. At work she is pretty loud and would express that I'm her husband or her love and would pretend to get pissy if I didn't say I loved her back. She would confide in me pretty often and show me screenshots of other coworkers sliding in her DMs saying all the down bad and we would share a laugh about it. While she does hang out with other male coworkers, she's been pretty clear about how some of them are a little pushy to get her in intimate settings like having a movie night, then weeks later she would suggest that her and I make weekly dinners and movie/series a thing after work since I live in between our work and her house. She buys me food all the time and never asks me to pick up the tab but I try to reciprocate since it's a nice thing to do but it's probably 50/50. She's made some pretty forward sexual remarks while working together. For example, she told me a story about the last dude she dated couldn't make a steak half as good as mine and every time he would cook her dinner he would specifically ask if it matched up, she then immediately followed up that story by looking me in the eye and saying "like seriously, you need head?" One time during a low acuity job we were moving some things around and I was bent over picking something up, she continued backing up towards me and made eye contact while smiling until her booty was in my face while the other guys around were watching. She also leaves me these notes to find that have drawings or descriptions of sexual scenarios like "come home to your real lover" or "im crazy and need restraints winky face". I already said we were really close and have shared tons of life context with each other, pretty much no conversation was boundary breaking. We ended up doing high doses of mushrooms together and she helped keep me grounded when I was struggling through it but was insistent I didn't make her uncomfortable and that she would love to do it again. To wrap up this section, I'd say this behavior between us was pretty consistent throughout and it didn't matter if either of us were single or dating because she would act the same.
Why I think she might not be into me-
For starters, the majority of her friends from work that she hangs out with are men. Perhaps a bit of insecurity on my part, but I am aware that I don't know what she says or does outside of work with those people and I acknowledge she could easily say the same things about me to the other guys that she's been saying to me. She also has significantly more dating experience than I do, I have only ever been in a few long term relationships and I am not a big fan of dating, I think she's been through at least that many relationships at least in the time that I have known her. She has flaked on me close to last minute once or twice and is always running late. She's told me about how her 'ideal type' has changed over the years, this type is a different ethnicity than me. I acknowledge that she could also just be really comfortable/confident with herself and what she's looking for so some things that seem like interest to me might just be her not filtering.
my take-
I feel like at a minimum we have a strong a friendship and are genuinely close. She has supported me emotionally and I don't exactly feel like it's a one sided or fair weather friendship. I know she has ADHD and has been working on managing her symptoms for over 10 years doing a lot of work in therapy. She is pretty clear about being quite disorganized and running late to literally everything which I can respect. Obviously just because she is in therapy doesn't mean she's super healthy or even aware of how she acts all the time. While I value our friendship regardless of any romantic component, part of me treads carefully and observes our interactions. If I had to make an honest guess about our dynamic, I would say that there could be a genuine mutual attraction but a lot of the fun/tension comes from the uncertainty and lack of labels.
I'm not asking whether or not I should date or pursue her, and I am aware that if we are close like this opening the dialogue would be the best way to find the clarity. More or less I would appreciate hearing your experiences if you have had a close friendship where there are a fair amount of green flags and the worst of them seem more like yellow or conditional instead of red. I wont lie, I think about her a lot and I am very fond of her. I could see myself pursuing her in the future since I don't feel like I have had a relationship with a woman this close, borderline inclusive of my own dating experience in terms of feeling this mix of support and fun. I know I said I try to avoid dating coworkers but I wont be at this job for much longer.
tl;dr: known this friend for about 3-4 years, we have both been in and out of relationships. I feel like she treats me differently than others at work but she also hangs out with other guys. She and others have told me that she treats me better or differently. She flirts with me whether or not im in a relationship. She has a lot more dating experience than I do, I may be insecure that she is just enjoying boyfriend adjacent activities without the commitment, but she has never tried to get me to break up or talk bad about my partners when I was dating. If you want more context just look for the section related. thanks!