Jon sits down with Andrew Postman (Glamour's "Jake: A Man's Opinion," 1990–94) and Ky Henderson ("The Guy Guru" at Cosmo 2006) to talk about life as male advice columnists for women's magazines in the '90s and 2000s. They swap origin stories — how each landed the gig almost by accident — and dig into the mechanics of the job: where the column ideas actually came from, the freedom, how they came up with topics and answers, and how their own dating lives bled into the columns in real time. They also reflect on the twilight years of print magazines and the lessons learned navigating freelance careers as the industry shrank.