This story is based on an interview with Jackie Crenshaw, 61, of East Haven, Connecticut, the senior manager of breast imaging at a cancer hospital. It has been edited for length and clarity. As I approached my 59th birthday in the summer of 2023, I thought about retiring. I had healthy investments and a robust 401(k) after working a six-figure-salary job for many years and saving about 15% of my income. The prospect of change made me think about having someone to hang out with — a companion to