"I Still Pay My Ex-Girlfriend's Bills"

Alan, 26, calls from Los Angeles with a question that sounds logistical but turns out to be existential: Should he keep financially supporting the woman he dated for four years, who broke up with him after her mother died of cancer, and who now lives far away, barely communicates, and may be seeing other people?

The surface question is about money. The real question, as Dr. John Delony hears it, is about who Alan is becoming.

The relationship that won't end

Alan met his ex in late 2022. The first two years were good. Then in May 2024, her mother was diagnosed with stage four cancer and died four months later. She moved to be with family, the relationship went long-distance, and by 2025 they separated. But after a few months, she reached back out. Now they talk often. He sends money for bills. She doesn't share much about her life. When Delony asks if she's seeing other people, Alan says, "Probably if I'm being honest."

Delony presses: "She walked away from you. So you calling and saying 'should I walk away' — sounds like it's already been done."

Alan agrees.

The mechanism: outsourcing your worth

Delony reframes the entire problem. It's not about her. It's about Alan at 26 years old, looking at the totality of his life and his actions, and asking whether he is proactively becoming the man he wants to be. Alan's answer: no.