To be clear we are NOT coworkers, but we have known each other through our respective jobs for over a year and deal with each other on a 1 on 1 professional basis multiple times a week. We both recently became single and have talked about going out for a drink together one night. I’m also not sure she’s even really interested in me, or if I’m just not used to having a work friend this close
TL;DR is above ^^ I like to add context and tend to ramble a bit when I do, so for anyone who cares to read the whole situation the details are below
We’ve known each other since the beginning of last year. I was fairly new to my job when I was introduced to her on her first day as the person who I would be dealing with at that business from then on. Tbh I had a crush on her from day 1. We vibed immediately and became fast friends. I’m in her workplace before they open and it’ll be just me and her, normally my job is very quick in and out, but we would always linger and chat for a bit. I am notoriously bad at picking up on signals from women, but I really felt like there was a tension between us. I would catch her smiling to herself as I was walking out, and I really felt like she was interested in me too. But with this being a work situation (and me being older), I played it safe and professional, kept it friendly and was careful never to cross the line to overt flirting. I was content getting to know this wonderful person 10-15 min at a time, 5 days a week. This went on for about 3 months, and to that point she had never mentioned anything about dating anyone, only talked about exes. We actually live in cities 90 miles apart, but she went to college in my city. One day she mentioned how she was taking a day off to drive up to my city for a doctor appt, how she was driving up alone and was looking forward to eating at a restaurant she missed. I thought that was her giving me a cue to ask her out, so I told her if she would like some company on her lunch to let me know. That’s when she hit me with the “oh, idk how my boyfriend would feel about that.” It was very awkward in the moment, but the next day I came right in busting jokes like I normally would, like nothing ever happened, and our friendship went on unphased. I moved on and got myself a girlfriend less than 2 months later. But not before she tried to set me up with a friend of hers (although she had to have known I wouldn’t really be interested in this friend of hers)
Fast forward to after Thanksgiving. I come into her work one morning and find her very emotional. She tells me how her boyfriend broke up with her, and she ends up crying on my shoulder as we hug for several minutes. Unfortunately not long after that, her work ended up changing her schedule around and I was lucky to see her once a week for almost the next two months. I really liked the girl I had been dating, but we had kept it fairly casual and she ended up breaking it off early February saying she didn’t want to be in a relationship right now but wanted to remain friends 🙄 (which is a whole other situation I could dive into on here).
Coincidentally my work friend/ former crush started opening more often again right around that time, and since then we have become even closer friends than before. My crush on her and the feeling of tension between us also came back very quickly. In the past maybe 3 weeks in particular there’s been several times where we’ve stood there talking over 30 minutes, which is a looong time for my job (and hers), she’s been making me coffee or food some mornings. Our talks have gotten much more personal, from sharing deep family trauma, personal failures, the meaning of life and the universe, even her telling me about a sex dream she had and brushing up on sexual topics a couple of other times.
Recently we’ve been talking about me driving to her city one night when we’ll both be off the next day and getting a drink together. But I’m hesitant on both a personal and professional basis on whether or not I should make a move. Ive come to genuinely value her friendship, and I’m scared to lose that if she were to reject me. And then we would still have to deal with her at work, I wouldn’t want to make her feel uncomfortable or awkward in her workplace if I’m reading things wrong. What do you guys think I should do?