I've actually had a couple of friends of the guy I like come up to me and ask me crazy stuff...for example..i was getting my hair dyed at the salon when his best friend comes in stares me down and asks me if I got permission from the guy I like to dye my hair..and one of his other friends asked me if I'm bossing him around...and when I went with friends for a coffee he was there with a bunch of his friends and he was outside and his one friend told me that my boss was outside..lol..then I told him I was the boss...then he came inside..he acted different though, not like he usually does around me at work(all funny and touchy and flirty) he was quiet and shy, had his hoody almost covering his face....
Opposites attract. He's shy, his friends are outgoing. They are asking you (who's probably outgoing) questions because he's being a pussy and won't. They're trying to show that it's easy and that he needs to man up.