At 73, She’s ‘Sitting On Millions,’ But Her Financially Irresponsible Boyfriend Needs Help. Should She Bail Him Out Or Protect Her Fortune?

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…


At 73, She’s ‘Sitting On Millions,’ But Her Financially Irresponsible Boyfriend Needs Help. Should She Bail Him Out Or Protect Her Fortune?

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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When she first started dating after being widowed in 2016, she made one thing clear: she was “financially solvent and wanted the same in a partner.” Over time, she realized he had interpreted that “quite loosely.” He had multiple credit cards, liquidated a 401(k) after his divorce to spend a year abroad and had what she described as “a bad Amazon shopping habit.” His apartment, she said, was “borderline hoarder territory.”

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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The internet had thoughts.

Many commenters blasted her for prioritizing money at this stage of life. “At 73 being financially secure why in the world would you care,” one wrote. “You’re 73, sitting on millions, and not willing to help out a ‘kind, caring, intelligent and emotionally supportive’ partner?” another added. “Definitely leave him. You’ll be doing him a favor.”

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.

For many people, especially later in life, these decisions can feel like high-stakes. Protecting assets while maintaining relationships isn’t simple. That’s where outside guidance can help. WiserAdvisor offers a free way to connect with vetted financial advisors, especially for households earning $100,000 or more. There’s no obligation to hire, but having a professional sounding board can bring clarity when emotions and money collide.

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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This article At 73, She’s ‘Sitting On Millions,’ But Her Financially Irresponsible Boyfriend Needs Help. Should She Bail Him Out Or Protect Her Fortune? originally appeared on Benzinga.com

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