Jamie Reillis, an Executive Recruiter for a prominent job agency in New York City, played by Mila Kunis, finds herself entangled with Dylan Harper, portrayed by Justin Timberlake, an art director from a small internet company in Los Angeles. Both are fresh off breakups and are disillusioned with the typical Hollywood trope of “perfect love,” choosing instead to keep their hearts guarded.
Tasked with persuading Dylan to interview for a position at GQ magazine, Jamie invites him to New York City. Upon arriving, Dylan learns that Jamie successfully managed to have GQ extend him an offer. Initially reluctant to leave sunny Los Angeles for the bustling streets of New York, Jamie makes it her mission to show him the city’s allure. Over a lively evening that includes leading a contagious 'flash mob' dance in Times Square, Dylan eventually agrees to accept the job offer.
However, a new complication arises when Jamie presents him with the contract, as their bond begins to deepen beyond mere professional encounters. As they hang out, watching romantic comedies, they delve into the complexities of relationships and ultimately conclude that emotional ties should not complicate their physical connection. They agree to engage in a series of no-strings-attached encounters; however, Jamie eventually comes to realize that she yearns for something more meaningful.
After beginning a lackluster relationship with Parker, Jamie faces heartbreak when he proves to be uninterested in commitment. Seeking solace, Dylan suggests a trip to California to help her heal. Despite her hesitance, Jamie ultimately agrees, and the trip leads to a series of shared, intimate moments with Dylan as they navigate their feelings.
When Jamie mistakenly overhears a conversation that implies Dylan does not truly care for her, she retreats back to New York, determined to sever their connection. Back in the city, a series of misunderstandings and confrontations ensue, forcing both to confront their true feelings. With a poignant conversation with his father, who struggles with Alzheimer's, Dylan reflects on lost love and makes a breakthrough realization regarding his feelings for Jamie.
Determined to express himself honestly, Dylan enlists the help of Jamie’s mother to set up a heartwarming surprise at Grand Central Station which involves yet another flash mob. As he catches up with Jamie amidst the lively crowd, he confesses his true feelings. Surprised but elated, she reciprocates his affection with a kiss, leading them to cozy up together at a nearby café, where the night culminates in a warm embrace and passionate kiss—marking the start of what may just be the genuine romance they both were seeking.
