I Watched My Lonely 60-Year-Old Dad Give $20,000 to a Homeless 21-Year-Old He Met as an Uber Driver — And It’s Destroying Him

My dad, who’s 60, has recently become involved with a 21-year-old woman he met while working as an Uber driver, and I’m witnessing what feels like an emotional and financial disaster unfolding. She told him she was homeless, and since then, he’s been covering her hotel expenses, got her a job, bought her a car, and overall has given her around $20,000 in just two months. The heartbreaking part? He doesn’t have much saved for himself—his credit score is terrible, in the low 300s, and he’s even borrowed money from me without being honest about what it was for.

Friends and family have tried to warn him repeatedly. A friend of hers even contacted him claiming she’s still involved with her ex and using him for money. The ex’s mother has also expressed concern, but he brushes it all off, convinced they’re just jealous or mad at her. It’s surreal watching my dad, who looks like Danny DeVito (no offense), no savings, and very lonely, believe this woman truly loves him. They’ve only known each other two months, but he’s already tattooed her name on his body. He’s had to retrieve the car he bought her from the police more than once, and recently signed the car over to her officially.

He insists she never asks for anything, yet somehow he’s drained $20,000. I’m stuck trying to figure out how to help him see what’s happening without pushing him away. I’m torn between intervening or letting him feel the consequences and then helping him recover. I fear the situation is worsening too fast.

He’s always been terrible with money and very lonely. The VA sees him yearly, and while he gets care for mental health issues like anxiety and PTSD, I’m beginning to worry about possible early dementia or cognitive decline, which might be worsening his judgment. Some have recommended contacting Adult Protective Services to assess his wellbeing.

He thinks giving money to this woman gives him purpose and love. But I see a man being manipulated. He’s got a fixed income, and she likely stays for that steady financial support. I have told him I won’t bail him out financially if things go south, and suggested he see a financial advisor—there might be gift tax implications he doesn’t understand.

I wish I could make him understand that this woman, who’s young and has a boyfriend, is using him. But all I can do now is watch, worry, and hope he wakes up before losing everything.

If you’ve seen this happen before, how do you help someone so far gone? I’m heartbroken and helpless.