So, I started working my current job when I was 18. I’d never had any sexual/romantic interest in another person at this point in my life, and never thought I would, until I met my boss.
He was a breath of fresh air compared to the younger boys I worked with, had a great sense of humor and was really easy to tease/get flustered, which I enjoyed. He’d tell me I was like a little sister, easy to read. But like most of these stories go, he was already in a relationship.
He would randomly mention his fiancee when we spoke so I took that as a signal to stop speaking to him so much, which I respectively did even changing shifts to give him space. Some months went by and it was kind of awkward between us because a mutual friend had told him I was crushing on him and he kept asking why I was dodging him, he felt lonely.
I eventually transferred out, and my super gaga high-school crush on him faded away too.
Now three years later of floating between stores and promotions for the both of us has landed us back at the same location working side by side, though he is still my boss.
He is still the first and only person I’ve ever really felt attracted to, and three years didn’t really change that. I was ready to put this awkwardness behind us and just focus on work when he started coming to me asking questions like, “Did you miss me like I missed you?” “Did you come out of your shell and get a boyfriend yet?” “I was thinking about you.” “You wanna get lunch sometimes?” etc etc….
I just flat out ignore these questions and change the subject. I never ask him questions about his personal life, and I’m not sure if he’s asking because he is genuinely interested or for his own amusement at making me blush. We still have a great dynamic going together which I don’t want to ruin. I guess my question is how do I figure out exactly how he is really feeling behind all the teasing we do?
Do not date your player boss.
First, consider if he is single. Second, consider his fiancee, they might be married by now. She might be one bad a__s who might hurt you for messing with her man! Third, if the relationship went sour, you might get fired for bogus reasons.