A 73-year-old widow says she’s “sitting on millions,” but is watching her 74-year-old boyfriend “circling the drain” financially.
They have been together since 2018, she wrote on Reddit’s r/Rich recently. He’s a retired lawyer who was working full-time at a Medicare call center until recently losing his job. His 2012 Kia just died. He has outstanding loans against his 401(k) and won’t be able to repay them in time to avoid taxes.
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Love, Money And A Late-Life Dilemma
Still, she stayed. “He’s a nice guy — kind, caring, intelligent and emotionally supportive,” she said. They split dinner bills and took occasional road trips, usually using her more dependable car.
Now that he’s unemployed and without transportation, she’s torn. He knows her net worth and has “never tried to make his financial problems my problems,” she said. But she can’t ignore the contrast between his instability and her wealth.
She’s also planning to move to another state later this year and hasn’t given up on finding a new relationship. “This time I swear I’m gonna ask for financial statements up front,” she wrote.
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Reddit Reacts
The internet had thoughts.
Others argued the issue wasn’t money but responsibility. “It’s not about you not wanting to spend the money,” one commenter said. “It’s about you wanting someone who has gotten their sh*t together by the time they reached their 70’s.” Several pointed to her description of hoarding and long-term financial mismanagement as red flags.
The debate quickly turned philosophical. “You can’t take it with you,” one commenter wrote. “So you might as well enjoy it with people you enjoy while you are here.” Another quoted late reggae singer Bob Marley. “Some people are so poor that all they have is money,” they said.
The woman later updated her post. She offered him $20,000 as a gift. “No questions asked on how he spends it, not a loan,” she said. “He was overwhelmed and accepted it.”
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That move seemed to strike a middle ground: compassion without full financial entanglement.
Her hesitation wasn’t random. In comments, she revealed a painful history with her ex-husband, who struggled with debt and addiction. She had covered his bills, taken loans in her name and sent money to creditors. “I was co-dependent and didn’t realize it and it cost me,” she wrote.
In the end, the real question wasn’t just whether she should “bail him out.” It was whether financial instability at 74 reflects temporary bad luck or a lifetime pattern she doesn’t want to manage again.
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