Host Ira Glass talks to Chicago Tribune newspaper columnist Amy Dickinson ("Ask Amy"), the heir to Ann Landers, as she reads letters from those readers who don't yet know their love is doomed. (7 minutes)
Comedian Jillian Welsh tells Diane Wu about one of the most romantic—and stressful—nights of her life, a night that paralleled the plot of a rom-com in several ways. A version of this story first appeared on the Risk! podcast.