Christian (James Deen) is a wealthy young man who produces low budget horror films. At the start of the film, he is having dinner with his girlfriend Tara (Lindsay Lohan), his personal assistant Gina (Amanda Brooks) and her boyfriend Ryan (Nolan Funk). Christian has recently secured a leading role for Ryan in one of his films. Christian reveals that he and Tara have an open relationship and use dating apps to find partners for group sex. In discussing this, Christian outs Tara as bisexual. He says that he trusts Tara never to fall in love with anyone he brings into their bed for casual sex.
Christian and Tara leave the dinner to prepare for the arrival of their latest dating app paramour. Tara is unhappy that Christian outed her as bisexual, demanding Christian tell her what he tells his therapist as quid pro quo. Christian refuses and the argument ends abruptly when their date arrives. Christian orders the man to strip and masturbate while watching Tara and Christian engage in oral sex, all of which Christian records on his phone. Meanwhile, at their apartment, Ryan accuses Gina of wanting to have a four-way with Tara and Christian, which Gina denies. Ryan texts an unknown party for a meeting the next day.
Ryan’s text was sent to Tara, who meets him the next day. Through their conversation, it is revealed that the two are former lovers. Tired of life as a struggling actor, Tara left Ryan to date a string of wealthy men, sacrificing her acting career in the process. Tara chides Ryan for texting her, as Christian monitors her texts and calls. They argue, with Ryan insisting Tara is degrading herself for a life of luxury and Tara pointing out the favor she did Ryan in getting him cast in Christian’s film. She demands they not see each other again.
Christian visits an actress named Cynthia for casual sex but the encounter nearly ends when he starts choking her. Christian confides that he thinks Tara is cheating on him. Tara meanwhile has lunch with Gina, telling her she will not be traveling with the rest of the group to the set of Ryan’s film. Gina then gets a call from Christian, whom she informs of Tara’s decision to stay in Los Angeles.
The film cuts to Ryan, who is desperately looking for extra hours tending bar. His manager uses this as an excuse to make a pass at him; Ryan gets a text and steps away. The text is from Tara, who has changed her mind about not wanting to see Ryan. Christian follows Tara and sees her with Ryan. Christian then goes to Gina’s friend John, the boyfriend of the film’s producer. Christian orders him to call Ryan and tell him that he’s about to be fired but he can save his job by sleeping with John, calling it a “prank.”
Returning home, Christian grills Tara on her activities that afternoon and the subject of Gina and Ryan’s attractiveness. Tara denies being attracted to Ryan or knowing him previously. Meanwhile, Ryan discovers Christian’s daily schedule on Gina’s computer, noticing regular “yoga sessions” with Cynthia. Ryan gets a text to meet with John, who propositions him per Christian’s demand. Ryan shocks John by asking him if he wants to have sex then and there, pulling out his penis so John can perform oral sex on him. The film cuts to Ryan leaving the building, leaving it ambiguous whether they had sex or not.
Tara receives anonymous texts asking her about her relationships with Ryan and Christian. She tells Christian she is going to see a movie with a friend, but instead visits Cynthia, who is revealed to have been Christian’s girlfriend before Tara. Cynthia tells Tara that she needs to leave Christian and admits to sending the anonymous texts. Cynthia reveals that she left Christian after he drugged her, orchestrated a group assault on her and recorded the incident. When confronted, he brutally assaulted her and threatened to release the video if she told anyone about his actions. Tara rejects Cynthia’s warnings and implies she plans to “hurt” Christian.
Tara returns home, at which point she admits to visiting Cynthia. Christian acknowledges dating Cynthia but denies beating her or arranging the assault. Suddenly Christian’s phone rings; a dating app friend is about to arrive. Christian offers to cancel but Tara insists they go through with it. Tara and Christian engage in group sex with the couple who arrives at the house. The male guest forces himself on Christian; Tara eggs him on, watching Christian receive a blow job.
Meanwhile, it is revealed that Ryan put Cynthia up to warning Tara, with it implied that the two are former lovers. At a record/movie store, Ryan realizes he is being stalked. Ryan then realizes Christian has hacked his bank account. The next morning, Tara calls Ryan but no one answers. Christian wakes up and violently assaults Tara, revealing that he knows all about her and Ryan.
Gina, meanwhile, finds Ryan drinking and asks if anything is wrong. Ryan admits to looking at Christian’s schedule on Gina’s computer, then tells her the movie is not going to get made. Ryan reveals he has been sleeping with Tara. Gina dumps Ryan, who is unapologetic about his obsession with Tara. Gina announces she will do whatever it takes to keep Christian from killing the film and have Ryan fired and banned from the set.
At his therapist’s office, Christian complains that Tara manipulated him into the homosexual encounter the night before. Christian rants about his need for control over everything in his life, especially Tara, and how his interactions with his therapist are not the “real” Christian. It’s revealed that Christian’s therapy sessions with Doctor Campbell (Gus Van Sant) are not voluntary, but rather a condition of the trust fund he lives off.
The film then cuts to Christian and Ryan, each driving through downtown Los Angeles. Christian leaves a message on Ryan’s voicemail, mocking Ryan’s failed acting career and revealing the details he has managed to obtain about Ryan’s life. Christian arrives at Cynthia’s house and forces his way in, accusing her of lying about being drugged and gangraped in an attempt to break up his relationship with Tara and win him back. Cynthia denies this but an enraged Christian stabs her to death. Returning home, Christian finds Tara packed and ready to leave. Christian apologizes for brutalizing her and agrees to let her leave their relationship on two conditions: 1. She must give him an alibi for his murder of Cynthia and 2. She must never contact Ryan; if she refuses, he will murder Ryan and use his family’s wealth and connections to get away with it. Tara agrees and is allowed to leave.
The film ends with a flash forward to several months in the future. Tara is living in Dubai and having lunch with a friend. The friend asks about Gina’s film, as well as her relationship with Christian. Tara says she left the project when she and Christian broke up. The friend brings up Cynthia’s death and how no one was ever arrested for the murder, though it’s implied that Christian planted the murder weapon in Gina’s car in an attempt to frame her. Tara insists she is on good terms with Christian. The friend leaves to use the restroom, where she makes a call on her cell phone. She reports that Tara is doing well but clearly lying about being friends with Christian and about being happy in her new life. The final shot shows who is on the other end of the call: Ryan, alone in an empty room, still madly in love with Tara.