Search Results: asking his crush out

I have a huge crush on a man who I have a flirty relationship with. The flirting is often sexual and he acted jealous when he found out I was talking to his male colleague.
I don’t see him much anymore because I have a new job. He asked me if I like my new job and then instead of asking me what I do etc., he asked me if “there are any nice looking guys” and if I’m “getting laid while being paid”
I saw him today but he was driving towards me and I had to run out of his way (he didn’t wait for me to cross road before he left the junction). I saw him face to face an hour or so later and he said “how come you didn’t wave to me? Does your arm hurt when you lift it?” And then I said that my arm does hurt because I’ve been working hard in the gym and he said “Nia (my personal trainer and one of his ex members of staff) looks good doesn’t she?” And he flexed his arm.

I work as bar staff at a restaurant and my co worker who’s the same age as me (early/mid 20s) is also one of my supervisors. He has a girlfriend he lives and bought dog together and all that. Despite that he’s still asked me some very questionable questions or said strange things like asking if I enjoy being single, guessing how many people I’ve slept with, saying he can guess what my type is, saying he enjoys being in a relationship despite admitting to having been a manwhore and sleeping with 50+ girls before girlfriend. He’s asked me to rate him out of 10, so I asked back about me and he said 8.

I though some of these interactions was just the work environment I was in and that he’s an incredibly social person but today he said he could guess what colour underwear I was wearing, saying red (wrong), I asked the other girls and they said he’s never asked them that before. He does like to wind me up all the time and see me get annoyed and likes to joke that I have a crush on him just because I said my type is Latin looking, dark hair & eyes, thick dark brows and that. I don’t feel that way towards him and I wouldn’t entertain it in that way if he tried anything. He’s not “physical” but he likes to steal pens and my phone from my butt pocket all the time. Reminds me a bit like a little kiddo who has a crush, but I’m so confused if he’s just being friendly or actually likes me? He does enjoy making me laugh as he’s quite funny, but I don't know what to think of it as we’ll talk pretty openly about sex life and his and his girlfriend sex life even? (Which doesn’t make me feel uncomfortable, it’s just kind of unusual).