19-year-old Jill proudly calls draining her 6 ex-boyfriends and ex-husband's wallets her “career,” shames parents on social media for daring to ask her to repay her “earnings”: ‘Jill broke down crying and tried to convince that she is too pretty to work’

Author image for Etai Eshet
Etai Eshet • Editor
May 29, 2025 10:00 AM EDT

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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  • Entitled SIL thinks lying to her exes in order to get money out of them is a valid career

    "She's managed to get thousands of dollars from these men"
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  • I my SIL (19F) let's call her Jill, is extremely spoiled. She's tall, beautiful, and charismatic which she constantly weaponizes. My in-laws are some of the best people you'll ever meet, but if
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  • you asked her, they're horrible, manipulative and they kicked her out the moment she turned 18. In reality, Jill left of her own accord and moved in with boyfriend #1 (18m).
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  • She left bf #1 after he refused to buy her a high end purse. Keep in mind he was also 18 at the time had been buying her everything she wanted up to that point. Jill had a new boyfriend, bf #2, no less than a week later, one of bf #1's "friends". The cycle began all
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  • over again and after about 3 weeks of dating, bf #2 refused to pay for her next tattoo. Then I get a call from her telling me about how ab ive he is and so my
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  • husband and I offer to allow her to move in with us. She refuses the offer but does ask if we will pay for her new apartment rent. We decline but say she can always stay with us.
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  • Back in October she also got married in secret to a military man (19) but left him about 4 months later after he refused to
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    The image does not depict the actual subjects of the story. Subjects are models.

  • make their marriage open. After that, according to her, he became very ab ive because he wouldn't let her take HIS car.
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  • This cycle keeps happening and at this point she's now officially broken up with BF#6. She FINALLY agreed to move back in with her parents but only under
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  • the agreement that she get a job (which she has not had) and that she remain single for at least 3 months so she can just focus on herself.
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  • After an unrelated mental health crisis, that I will not get into, her mother was granted access to Jill's text messages and emails. And this is where things take a turn. She discovered that over the last two years, Jill has not only
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    The image does not depict the actual subjects of the story. Subjects are models.

  • been in contact with boyfriends 1-6 and her ex husband on a regular basis, but has also been consistently mooching off of them and lying to them in order to get money from them. She's
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  • told them all everything from wanting to get back together to being homeless to needing to escape whatever relationship she's in.
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  • She's managed to wrack up hundreds and possibly several thousand dollars from these men by making false promises and the worst part is what she's told them
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  • about her family including me and my husband. The family that's never done anything but support her and love her and offer her a safe place.
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  • We all managed to sit down with her, and express our concerns with her behavior. Her mother, who is no pushover, told her that if she wanted to keep the car they've been allowing her to use, and for her parents to keep paying for her phone bill and in
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  • order to continue to live under their roof rent free, she needed to give back all of the money she's stolen from these men. Jill erupted. She started going on
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  • about how all of these men were ab ive and that the least they could do was pay her for the mental anguish she'd had to deal with.
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  • That's when I decided I couldn't take it. I had to get up and leave the room because if I didn't, I was going to say something I'd regret.
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  • The meeting ended when Jill stormed out of the house got in her parent's car and left. My husband told me that basically, Jill broke down crying and tried to convince her parents and him that what she was doing was her "lively hood", her "career". That
    via terpi0-0
  • she is too pretty to work in a fast food or in a retail setting so she sees swindling her exes out of money as a perfectly legitimate way of "earning a living". While she's not obligated, I guess, to give that money back, it's completely scummy and immoral her parents are horrified. They
    via terpi0-0
  • told her that if she didn't give what money she could back and start seeking professional help, then she'd be cut off financially and from the family basically altogether.
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  • It's been a few days now and Jill has been all over social media talking about how ab ive her FAMILY is now. How they stole her savings (aka made her give back the money she took). I've wanted to respond to these posts to set her straight but refrained from doing so at my husband's
    via terpi0-0
  • request. Last I heard from her mom, Jill's given what money she can back to the exes and cut off contact with them. But I guess we'll just see how long that lasts as, apparently she's already found a new boyfriend and plans on moving in with him.
    via terpi0-0

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family drama inheritance brother mother tradition siblings family feud favoritism wedding aunt in laws mother in law sister fiancé grandmother Father
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