Prudence is joined this week by writer and activist Jaclyn Friedman. Together they tackle questions about whether it’s ever ok to misgender someone when talking to a doctor, when to establish boundaries when working as a personal assistant, how to think about your own sexuality when your parents and therapist have reacted with homophobia, where to look for new purpose and joy at an older age, what kind of conversation to have with your in-laws who put their dirty shoes on the couch, and how to navigate wedding invites to friends who have multiple partners (and some of whom you don’t like). Slate Plus members will hear Prudie and Jaclyn discuss an additional letter about how a young company might need to rethink their nude beach work outings. Not yet a member? Sign up at Slate.com/PrudiePod.Email: prudencepodcast@gmail.comProduction by Max JacobsLearn more about your ad choices. Visit megaphone.fm/adchoices