We live in the age of the gig economy and side hustles. Some people drive for Uber, some dabble in dropshipping, and then there’s Jill, age 19, whose signature move is “emotional extortion disguised as dating.” While her parents offer rent-free living, a car, and an unlimited phone plan, Jill’s entrepreneurial spirit leads her elsewhere: namely, a never-ending carousel of boyfriends and one very short-lived secret marriage. Each new sweetheart gets a crash course in romance, followed swiftly by a crash course in bankrolling Jill’s lifestyle, right up until the moment he’s told to fund her next luxury item or tattoo—or else.
Of course, when these cash flows dry up, Jill simply repackages herself, spins tales of homelessness and villainous exes, and moves on to the next generously gullible mark—sometimes recycling old flames for that extra sustainable touch. The revelation that she’s not just juggling suitors but running a full-blown multi-ex Ponzi scheme is met with shock and horror by her parents, who demand she repay the “investors” and, for good measure, get a job that doesn’t involve creative fundraising—or at least a little professional help.
Jill, naturally, takes her case to social media, framing herself as the true victim in a family of unsupportive monsters. But with her latest boyfriend already queued up, one can only wonder how long it’ll be before she’s back to business as usual, armed with a fresh round of self-pity and a new lease on questionable career choices.
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