"Fuckboy with a heart of gold" is that Cleo's kryptonite or what? I love that. She is originally from Staten Island, and has been in NYC pretty much since she turned legal, so she's been around and there's a definite chance that they've run into one another. He's definitely her type too, that's for sure.
I'd love to find clients that she gives private content to, and also exes, or ex flings/hookups. Maybe even an Alpha she frequents for both his and her own needs that time of the month? I don't have any of her sexual or romantic past mapped out, so she's totally open!