Male friend asked me to roofie him?

I have a crush on a guy I work with. We joke around a lot like dirty jokes and stuff. It’s really hard to tell if he’s flirting or if I’m just one of the guys. The other day kept joking about me roofing him, saying he wanted to get roofied and being like “oh no my cups wide open!” “why haven’t you done it yet?”. Do you think this was him flirting? We joke about sexual stuff, but this time he it seemed like he was implying he wanted me in that way.
Male friend asked me to roofie him?
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