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"Fleishman Is in Trouble" follows recently-separated surgeon Toby Fleishman as he enters the world of app-based dating and finds more success than he ever had the last time he was single. When his ex-wife Rachel disappears, he's left with their kids and no hint of where she is or whether she plans to return. Balancing parenting, friends, a long-awaited promotion at the hospital, and all the eligible women Manhattan has to offer, he realizes that he'll never be able to figure out what happened to Rachel until he can more honestly examine what happened to their marriage. Libby is Toby's long-time friend and the narrator.