Today’s episode features stand-up comedian and fellow Bostonian, Janelle Draper. She shares her insights on dating with large age gaps, as well as swiping on dating apps with her mom. How to handle your partner’s success without being resentful. Nina might be a witch who hexes people. The healing power of depressing music. Thoughts on reading your partner’s diary. And we ask, how do you tactfully ask a friend to have a threesome?

(00:00) Intro

(04:10) - Swiping on dating apps with your mom

(5:03) - Having negative patience for your parents

(08:33) - That deserves a slap

(14:47) - Heckled in Boston

(17:39) - Nina might be a witch who hexes people

(18:50) - Janelle does a sex education/comedy show with her sister who is a midwife

(21:17) - How do you tactfully ask a friend to have a threesome?

(27:27) - Liam turns into a pink boy when he’s embarrassed

(30:20) - Dating a younger man

(32:25) - Intimidated by your partner’s success

(33:32) - Covert hostility

(36:10) - Big age differences

(37:04) - Getting mistaken for getting younger

(38:10) - The wage gap

(41:15) - Living in the present

(46:02) - Listening to depressing music

(49:49) - Liam learns what Gwar is

(52:01) - Liam confesses his love for Sheryl Crow

(57:20) - Reading your partner’s diary

(1:00:20) - Self harming by snooping