The Line in the Sand (sure to be an ongoing topic)

Hi, Ladies 💜

So... I have this friend. Like, my best friend. He’s the bestest friend ever! And I love him to death. A little backstory on how we met: I interviewed to work at a music store as a teacher and was hired; he became my boss. Now, I had worked in many establishments that were primarily occupied by other women and was used to growing close to my coworkers. This was different: I was typically the only woman in the store. As such, I was wary about actually getting close to anyone there. However, he and I eventually started to socialize a little as he got to know me as an employee (my work is my life, so it’s hard to get one without the other from me). We ended up going through some crappy break-ups around the same time; as well as some other tough life stuff. Eventually, we would hang out after work, just talking in the parking lot about everything and nothing. By this point, we’re about 6 months into my working there. We’d become completely synchronized on the clock. Communication wasn’t even needed most of the time. And then, it happened: someone asked us if we were dating. I said no, because we weren’t. He said we couldn’t, because - well - we couldn’t (I never put much stock into that answer). This eventually became a thing that happened to us regularly, down to someone saying we should just sign a romance contract for work so we could date. I thought that person was crazy because this is my boss and best friend we’re talking about! He said it would never fly due to the nature of our department and work relationship. Again, didn’t pay much attention.

Today we’re no longer coworkers. He was moved to a different department and I resigned not too long after. We’re still best friends. And he still does ridiculously nice things for me. I asked him for an opinion on an outfit one night that I intended to wear for someone else and he went off on a tangent about how he has had bad luck with mixing romance with his friendships in the past. Now, I’m confused. I wanted an opinion on a dress. He’s calling me gorgeous but saying he can’t be with me 🤷🏾‍♀️ A small part of me wanted to bust the case wide open, but I left it alone. Because we’re best friends, we’ve never been shy about discussing personal things, down to bedroom matters. Even so, I was surprised when during one of my episodes of insomnia, he suggested that I fantasize about him, masturbate, and go to sleep. Not gonna lie. I did, it worked beautifully. Since then, our flirting is a bit more prevalent. I’ve seen his body many more times and even reciprocated with pictures of my own. Discussions of actually having sex are taking place now.

I have always drawn a line in the sand for us and it feels like he either nudged it forward when I wasn’t paying attention or dragged me over it. And it’s not that I didn’t want to push the boundaries; I just wanted to respect him and our friendship more. Should I just let things happen as he dictates or not? Should I stop this now before we get in any deeper?

Update: I’m going to ask him out for Valentine’s Day. I’m expecting a ‘no’; but what is the harm in asking?