Brian and Judson are joined by podcaster and documentarian Jess Rothschild, creator and executive producer of the GLAAD Award-nominated docu-series Finding Fire Island, now in its second season—with many episodes featuring Judson! Jess tells Brian and Judson how she came to fall in love with Fire Island, why she felt it was important to document its deep history, and asks each host to share their Fire Island origin stories. She also shares her views on 12-step programs, explains how she is attracted to women but prefers the company of gay men, and discusses the differences in how lesbians and gay men approach sex and openness. Finally, Jess helps Brian and Judson respond to a "Go Ask Your Dad" question from a listener who has found a spark with someone online but is unsure whether or not he should remind this person that they interacted years earlier—and that it ended on a sour note.