At thirty-three, comedian and educator Jake Jabbour found himself living alone after a breakup with his girlfriend and burying his grandpa. His most impactful relationships ended, stripping from him his identities as a roommate, boyfriend, and grandson. Hoping to discover who he was when he wasn't himself, Jake boarded an Amtrak train with his comedy partner to perform live improv across the country, from Los Angeles to New York, examining the trials, tragedies, and triumphs of his past that landed him alone in the most crowded cities in the country.

In the lineage of Chuck Klosterman's Killing Yourself to Live and John Steinbeck's Travels with Charley, Jake chronicles his cross-country travels with an eye trained towards relationships and culture, searching for clues and connections with others that might shine a light on his own identity. Along the way, Jake lays bare his thoughts on grief, nostalgia, family, failure, comedy, education, relationships, culture, and self-acceptance.