how do i word it so it doesnt sound like im asking him if he has ever been in jail.
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Have u ever met lil Wayne? :)
Tell him he has a pretty mouth and see if the PTSD kicks in.
If he is from the Bruce County... then more than likely has ended up in jail
where's the craziest place you've ever been?
Have you ever been away for an extended period of time? If so, did you get bum fucked? Was it consentual? Ahah