Director – Leslye Headland
Year – 2015
In 2002, Lainey causes a scene in a dorm at Columbia University. Taking pity on her as she is about to be kicked out by security, Jake claims her as his guest. He learns that Lainey was there in order to lose her virginity to her T.A., Matthew, who Jake thinks is the most boring guy in the world. Lainey eventually realizes that Jake is also a virgin, and the two lose their virginity to each other.
Years later, Lainey breaks up with her long-term boyfriend Sam after telling him she has been cheating on him. On the advice of her therapist, she attends a sex addicts meeting, where she runs into Jake, who is there because of his inability to commit. Lainey schedules an appointment with Matthew to end their affair; he agrees and tells her that he is engaged, but they end up having sex. On the advice of a friend, she contacts Jake, and the two go on one date where they confess their sexual problems to one another. At the end of the date Jake confesses that he wants to sleep with her; however, Lainey insists that the two of them should just be friends and Jake agrees with the safe word “mousetrap” to be used to deflate sexual tension between them.
The two hang out more and eventually become best friends, confiding in each other about their dating lives as they try to move past their commitment issues. Strangers mistake them for a couple and their friends begin to think they are in a relationship as well. Jake learns that Lainey is going to re-enrol in medical school and possibly move to Michigan. He brings her to the birthday party of his friend’s child where she meets Chris and begins seeing him to Jake’s chagrin. Jake decides to move on and asks his boss Paula on a date.
A date with Chris leads Lainey to run into Matthew and his now-pregnant wife. At the same time, Jake has sex with Paula and calls her Lainey. After their nights out, Jake and Lainey spend the night together where they realize that they are both in love with one another; however, they do nothing about it, afraid to mess up their relationship as they have with other sexual relationships in the past.
Lainey moves to Michigan and Jake devotes himself to Paula. Two months after Lainey has left, during brunch with Paula, Jake sees Matthew and punches him in the face. Paula breaks up with Jake after he refers to Lainey as “my girl” and Jake is arrested. He calls Lainey from the police station and confesses he is still in love with her and wants to pursue a relationship even if it fails. She tells him she feels the same way.
Sometime later, Matthew is suing Jake for emotional distress and refuses every settlement he offers. Lainey goes to see him and tells him she will tell his wife about their relationship if he does not drop the case. After leaving his office, Lainey meets with Jake and the two rush off to be married.