"Anybody who pays for an escort is PATHETIC!", said local businessman Phillip 'I picked up a hot hooker after prom' Burnell, who later went on to clarify that while he is a businessman, he does not own a business, especially for tax purposes.
As for finding women, he has a history of lying about romantic partners. Apparently he's lied about a fiancée to "win" forum arguments years ago, way before Leanna. Not to mention the Michael Scott-esque story of his dorm room being the "party room", where they'd just drink and fuck hot chicks every night. It's more than likely that Leanna was his first real relationship. And now he's taken to mistaking women seeing financial potential in him as them finding him "charming" and "funny".
As hilarious as it would be, it's obviously not the escort. Phil is dumb, but he's not stupid. Imagine the laziest, lowest-effort way to go about something, and you'll find the Phil Burnell Way™. In this case, it'd be going for some mentally deficient fangirl, or a straight up gold digger, who's messaged him in the past. Also, based on the timeline he's given, it took him a month to jump into a new relationship after just leaving a six(?) year long relationship and engagement. Fuck the Hungry Man dinners and his "Italian" "sauce" sugar water. That's just straight up the unhealthiest thing he's ever done.
It also occurs to me that, as far as she's concerned, it doesn't really matter if he has money or not. He'd obviously be willing to spend on her, even if it'd put him further into debt, but it's not something that'd affect her. All the more reason to keep her face out of this shit; she can pretty much just vanish after she's done wringing him out for cash.