How would a male customer flirt with a female bar manager?

jolee1
a guy comes into my work (he is what i would call a semi regular) he always comes in with a big group of guys/girls. i can't tell if he is single or not, but I'm going to assume single.
i get the vibe from him that he may be interested and be flirting.
i quite like the guy, and i get to shy around him to muster anything more than anything work related

some of the things i have seen is that we
1) Catch each others gaze across the room
2) he has on occasion said something rather silly that i know he would probably feel embarrass about saying.
3) he seems to linger a little longer when he stares.
4) i feel like he sometimes goes out of the way to be served by me.

or am i looking into it too much.

the other thing is, one of his younger brother's friends is an ex of mine. it was a terrible break up but three years ago. (i don't think the guy knows that but it could be awkward) i can tell this family is close as they seem to hang out with their separate groups together to form one large group at the pub of various ages?
Updates:
+1 y
he was in tonight with his brother. his brother was flirting with one of the other girls behind the bar, and i was flirting with the guy (the guy i like was also talking to the other girl too, but i think more in a general sense) Tonight my guy asked if i had a boyfriend/husband , he asked me twice my age.
He said to me about going someone where after work for drink, however he didn't ask in a question way it was more a statement as if it would happen as if to join him and his friends.
+1 y
i said i was working late, and he said how are you going to meet someone if your working late all the time. his pupils were big and he was fixated on me when he spoke. I get the impression he is very keen, but i wasn't sure if he was hitting on the other girl to because his brother def. was? also still not sure if he has a gf, why would he ask me about if i had a bf?
How would a male customer flirt with a female bar manager?
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