Back to the job, I used to work for this company about 5 years ago, and had a really good personal and professional relationship with the owners and other supervisors. When I came back a few weeks ago I started talking with one of the managers like old times, innocent flirting, joking around like nothing had changed ( I had to cut off all personal friendships with any men when I quit the first time as my ex was very controlling). Anyway after working a couple shifts with him, I get home after work and he had texted me his number.(I'm assuming he got it off of my file) he's been texting me everyday, nothing inappropriate just the hey how's your day going, type stuff. Well the last time we worked together he asked me if I had any plans for the night, I did, I told him I was playing hockey. He almost seemed disappointed. I honestly think he was going to ask me out :-|. im not opposed to this idea, I'm just not to sure what's going on. So looking for advise, is he interested, do I persue it, he's pretty shy so I may have to make the first "move". Or do I just keep doing what I'm doing and see what happens? It's been a long time since I've done this.
There's no policies against us seeing each other (technically he is one of my bosses). In fact I'm pretty sure the owners would be all for it. Like I said we all have a really good personal relationship. This job is also very temporary and I only work around 10 hours a week.