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Currently you are able to watch "Dear Sidewalk" streaming on Flix Premiere. It is also possible to buy "Dear Sidewalk" on Apple TV, Amazon Video as download or rent it on Amazon Video, Apple TV online.
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.
