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Dear Sidewalk tells the story of Gardner, a 24 year old mail-carrier, who is struggling to contend with his identity as his quarter-life crisis is in full swing. His regimented routine is thrown out the window when he meets Paige, a divorcee, enduring a mid-life crisis of her own. In this relationship there exists a synchronicity, as they find, despite their age difference, they're both confronting existential problems surrounding identity, love, and the choices in front of them.