In this episode, Damon Young (a writer, critic, and a self-proclaimed \u201cprofessional black person\u201d) joins Prudie (Jen\xe9e Desmond-Harris) to answer letters from readers who are obsessing about their lackluster high school tennis careers, their awkward interaction with their crushes, and whether participation in civil war reenactments is a dating deal breaker.\xa0\nIf you want more Dear Prudence, join Slate Plus, Slate\u2019s membership program. Jen\xe9e answers an extra question every week, just for members. This week she answers a question about what to do when a grandparent food-polices a toddler.\xa0\nGo to Slate.com/prudieplus to sign up. It\u2019s just $15 for your first three months.\xa0\nPodcast production by Se\u2019era Spragley Ricks and Daisy Rosario, with help from Maura Currie.\nLearn more about your ad choices. Visit megaphone.fm/adchoices