The film begins with Will Henry (Jemaine Clement), a graphic novelist and art instructor, adjusting decorations for the birthday party of his five-year-old twin daughters, Clio (Aundrea Gadsby) and Colette (Gia Gadsby). As he searches for his longtime partner, Charlie (Stephanie Allynne), he ends up walking in on her and Gary (Michael Chernus), a monologist she's having an affair with. Charlie tells him that she's not happy with their relationship and is leaving him for Gary.
A year later, Will lives in a smaller house and sees his daughters on the weekend. Though he has a good relationship with the girls and wants to spend more time with them, Charlie has doubts that he would be able to handle all parental duties. Charlie also tells him that she is marrying Gary and is having his child. One of Will's art students, Kat (Jessica Williams), asks him to dinner so that he can meet her single mother, Diane (Regina Hall). Will finds that Diane is attractive and likable, though she does not respect Kat's studies or, in turn, Will's career. Diane informs Will that she is already seeing someone, though Kat has tried to set her up with men before, and Will leaves after dinner.
One night, Charlie abruptly drops the girls off at Will's house and asks if he could take care of them full-time; their nanny has quit and she can't take care of them on her own. Though Will initially struggles, he soon becomes more organized. However, a bomb threat cancels their school day, and needing a baby sitter while he teaches class, he promises money to Kat if she watches them. When he goes to pick them up after class, Diane admonishes him, telling him that it was wrong for him to pass his daughters off on Kat when the latter needs her education, and that it's not good for the girls to be bounced around between parents. The twins are asleep, so Will is forced to spend the night at Kat's apartment. Will notices that Dianne is reading a book on graphic novels and she tells him that she has gained a new respect for Kat's passion. Diane admits that she broke up with the man she was seeing; she and Will kiss and are about to have sex, but one of the twins comes looking for Will and he leaves to go keep the girls company. In the morning, Kat asks Will to read a graphic novel that she wrote.
Will and Dianne begin a sexual relationship, and things become tense between Charlie and Will; both believe that the others' behavior is causing confusion for the children. Charlie calls Will one night, telling him that there's an emergency; when he rushes over she tells him that the girls have locked themselves in the bathroom, saying that they want to live with him. Distressed, she tells him that Gary has been having doubts about the wedding, because he believes she's jealous about Will's relationship with Diane and they kiss. The twins come out of the bathroom and as they take them to get ice cream, and Charlie promises Will that they'll talk about their relationship later. Will tells Diane about his kiss with Charlie. She asks him if he still has feelings for Charlie, and he says that he doesn't know, and asks if the feelings ever go away. She says that they do someday but, hurt, breaks it off with him.
Will meets Charlie and the twins in the park, clearly ready to patch up their relationship, but Charlie tells him that she and Gary worked through their problems and he is once again ready for marriage. Furious, Will leaves, and begins drawing revenge artwork against Gary. He stops to read Kat's graphic novel: titled "Mother Fuckers," it chronicles her mother's struggles with dating as a single mother, depicting Diane as becoming more disappointed and heartbroken with every breakup. Will finds Kat again, who is angry at him for hurting her mother, and gives her his own set of drawings to look at, drawings of him struggling with letting go of Charlie that he had been creating throughout the film. Later, she visits him at his home and gives him back his work, telling him that she could tell who it was about and that he needs to let Charlie go. She also flips to a panel he'd drawn of her mother and tells him that she showed it to Diane, and that Will should call her again and rekindle their relationship.
On the day of Charlie's wedding to Gary, Will attends but finds Charlie absent. Gary is trying to call her, and Will confronts him, punching him (after warning him) but also telling him that he knows Gary loves Charlie. Afterwards he goes and finds Charlie, who is afraid of making "another mistake," but he tells her that he never considered their relationship a mistake—just something that worked until it didn't. They decide to remain friends, and Charlie marries Gary. Will leaves on his own with some stolen flowers from the wedding, presumably to go visit Diane.Jemaine Clement as Will Henry
Regina Hall as Diane
Jessica Williams as Kat
Stephanie Allynne as Charlie
Michael Chernus as Gary
Aundrea Gadsby as Clio
Gia Gadsby as Colette
The film premiered at the Sundance Film Festival on January 26, 2015. On February 24, 2015, The Film Arcade acquired distribution rights to the film. The film was released on August 14, 2015, by The Film Arcade.
People Places Things received positive reviews from critics. On Rotten Tomatoes, the film has a rating of 76%, based on 51 reviews, with a rating of 6.9/10. The site's critical consensus reads, "People Places Things finds writer-director Jim Strouse in peak form -- and makes the most of talented stars who help breathe fresh life into familiar narrative territory." On Metacritic, the film has a score of 68 out of 100, based on 20 critics, indicating "generally favorable reviews".