[Rosalind is very different from Chloe. Tony's not too sure how much she wants to share "I'm now in love with a guy who may or may not exist and also I've confirmed if he was a panhandler I'd let him couch surf against my better judgment, no questions asked" though. Just kind of a personal matter.]

Lesson one: you don't ask Jack for advice, period. Full stop.
Lesson two: whatever he told you dump it, it'll get you an overnight jail stay, doesn't matter how unlikely that seems to be the case
So what are you dealing with? Bouts of random, crazed violence as well?