In this episode, Damon Young (a writer, critic, and a self-proclaimed “professional black person”) joins Prudie (Jenée 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.  If you want more Dear Prudence, join Slate Plus, Slate’s membership program. Jenée 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.  Go to Slate.com/prudieplus to sign up. It’s just $15 for your first three months.  Podcast production by Se’era Spragley Ricks and Daisy Rosario, with help from Maura Currie. Learn more about your ad choices. Visit megaphone.fm/adchoices