Chris is a 38-year-old convict who has recently been released from prison. At a surprise party to celebrate Chris's release from prison, Chris reunites with Carol, his former high school teacher, who was his penpal during the 20 years he was in prison and helped with his release. After encountering him again outside a restaurant where he abruptly hugs her and gives her a portrait he made of her, Carol begins to realize Chris may have a crush on her though her own feelings for him are complicated as she is married with a teenage daughter. After Carol urges him to try to meet and socialize with other women, Chris bikes over to Carol's home and kisses her, confessing that he is in love with her. Despite her deep emotional connection to Chris, Carol insists that they should try to be friends. Returning home, she approaches her husband, who now no longer sleeps in their bedroom, and tries to initiate sex, but he rejects her. Chris goes over for breakfast at Carol's, and he, Carol and Carol's teenage daughter Hildy get along well though the mood is spoiled by the arrival of Carol's husband, Tom. Chris also feels frustrated by the limitations of Carol's time, the fact that she is helping another convict get parole, his brother's betrayal by staying friends with the man who put him in prison, and his inability to find a job. Hildy becomes interested in Chris and befriends him. She is surprised to learn that he holds her mother in such high esteem and credits her with helping him get through prison. Despite her earlier words telling Chris they can only be friends, Carol continues her emotional affair with Chris. Chris asks Carol to spend one day with him where the two of them can finally be free. They meet up for the day and go out to dinner and an arcade before going to a motel. They consummate their relationship and confess their love for one another. The following morning, leaving the motel, they are seen by Tom and Hildy. Tom attacks Chris, who hits him in the shins before fleeing. Hildy disappears and is later found by Carol after some help by Chris. Carol apologizes for not paying enough attention to Hildy and prioritizing Chris, though Hildy reassures her mother that she was able to make a difference in Chris's life. Carol says the relationship between her and Chris was a one-time occurrence. Tom moves out of the family home, Chris gets a job, and Hildy breaks into Chris and his brother's home, where she leaves an art sculpture which Chris recognizes as a sign of forgiveness. Carol goes to visit Chris and tells him that their goals are ultimately incompatible since he wants a simple life and she now craves a more fulfilling one. Nevertheless she asks Chris out on a date, hoping they will get to know each other as they are in the present, to which Chris agrees.
The film had its world premiere at the Toronto International Film Festival on September 8, 2017. The Orchard acquired U.S. distribution rights to the film, with Netflix set to release the film shortly after. It also screened at South by Southwest on March 10, 2018. It was released in a limited release on March 30, 2018, before being released through video on demand on April 3, 2018.
Critical reception
Outside In received positive reviews from film critics. It currently holds a 95% approval rating on review aggregator website Rotten Tomatoes, based on 39 reviews, with a weighted average of 7.3/10. On Metacritic, the film holds a rating of 76 out of 100, based on 15 critics, indicating "generally favorable reviews".