Prudence is joined this week by Josh Gondelman, a comedian who has written for Last Week Tonight with John Oliver and now writes for Desus & Mero. His debut essay collection Nice Try: Stories of Best Intentions and Mixed Results is available now. Prudie and Gondelman dig into letters about if you should allow guests to speak kindly of your extremely unkind father-in-law at his funeral, how to handle a mother who doesn’t approve of your relationship, yet is bossy about your wedding plans, what actions to take when you boyfriend pees in the bed whenever he drinks, what to do when your parents side with a manipulative sister and her bullying boyfriend, how to help your husband tell better anecdotes that don’t turn people off, do you owe it to your Jewish community to be “more Jewish”, even though it’s not a big part of your identity. Slate Plus members get an additional mini-episode of Dear Prudence every Friday. Sign up now to listen. Email: [email protected] Production by Phil Surkis Learn more about your ad choices. Visit megaphone.fm/adchoices