Sleeping with Other People

In 2002, Elaine 'Lainey' Dalton creates a scene in her college dorm that captures the attention of campus security. Jake Harper intervenes, saving her from being kicked out, a moment that sets off a series of unexpected events in their lives.

During her college years, Lainey confesses to Jake her mission to lose her virginity to her teaching assistant, Matt. Jake, however, doesn't think highly of Matt, calling him the dullest person he knows, which opens the door to a deeper connection between Lainey and Jake.

Fast forward to the present, Lainey finds herself breaking up with her boyfriend Sam after admitting to cheating on him 16 times. Their toxic relationship has been marred by jealousy and accusations, including Lainey denying any wrongdoing with Sam's brother.

Feeling lost, Lainey attends a love addicts meeting where she unexpectedly re-encounters Jake, who is grappling with his own commitment issues following a breakup with his girlfriend Hannah. This chance meeting rekindles their connection and opens discussions about their romantic situations.

After reconnecting, Lainey learns that Jake has sold his online advertising business and is now interested in Paula, a divorced mother. However, Jake's pursuit of Paula is complicated as he navigates his feelings for Lainey, creating an intricate love triangle.

On a double date with Jake and his business partner Xander, Lainey and Jake dive into their sexual struggles. They agree to establish a friendship with a 'code-word' to help manage their growing tension and feelings for each other.

As their friendship deepens, Lainey confides in Jake about her unresolved feelings for Matt. Jake supports her in understanding the emotional dynamics in her relationships, strengthening their bond and making them more aware of their own feelings.

Despite their close connection, Lainey decides to date Chris, confusing Jake, who is simultaneously trying to foster a romance with Paula. This leads to an emotional rollercoaster for both as they question the nature of their relationship.

After a date with Chris, Lainey runs into Matt, now married and expecting a child, which shatters her composure. On a parallel track, Jake finds himself in an awkward situation with Paula, calling out Lainey's name, leading to moments of deep reflection.

A night filled with realizations ensues as Lainey and Jake acknowledge their feelings for each other but also confront their respective emotional baggage. While Lainey is struggling with her past with Matt, Jake is trying to work through his infidelities.

Lainey makes the decision to re-enroll in medical school in Michigan, prompting Jake to confront the possibility of moving on. However, he finds it difficult to cope with his emotions, leading him to take drastic actions during a brunch that lands him in a confrontation with Matt.

Jake's anger gets the best of him when he punches Matt during brunch, resulting in his breakup with Paula and a subsequent arrest. This chaos leads Jake to a vulnerable moment where he confesses his love for Lainey from a police station.

In the wake of the altercation, Matt sues Jake for emotional distress, refusing to settle despite various offers. The tension escalates as Lainey takes a stand, confronting Matt about their shared history and leveraging it for Jake's benefit.

Lainey confronts Matt directly, using their history as leverage to ensure that Jake's claims are recognized. This culminates in a pivotal moment for Lainey, allowing her to reclaim her agency while solidifying her affection for Jake.

With the legal battle resolved, Lainey and Jake finally reunite, ready to embark on their journey together. They decide to tie the knot, leaving behind their tumultuous pasts and stepping into a hopeful future as partners.