Based on the bestselling novel of the same name by Taffy Brodesser-Akner, the series follows Toby Fleishman, a recently separated man in his forties who got married before graduating from medical school and has now plunged headfirst into the new world of dating through apps, which has allowed him to experience the success he never had in his youth. Just as his first summer of sexual freedom begins, his ex-wife Rachel disappears, leaving him with their child and has not been heard from since. Toby balances his life between raising his child, reconnecting with old friends, a long-awaited promotion at the hospital, and a host of suitable women in Manhattan. But he realizes that the only way to understand what happened to Rachel is to take an honest look at their marriage.