In the midst of a humdrum existence as a Transportation Security Administration (TSA) agent at Pittsburgh International Airport, Kirk Kettner (Jay Baruchel) grapples with the unresolved feelings lingering from his past relationship with Marnie. Despite their two-year separation and her new romance with Ron, Marnie's presence continues to loom over Kirk and his dysfunctional family, as she frequently visits them at his parents' home. While trying to navigate this emotional labyrinth, Kirk unexpectedly crosses paths with the breathtaking Molly McCleish, who is traveling to a far-off location.
What Kirk doesn’t realize is that, unlike everyone else, he remains entirely unfazed by Molly’s enchanting allure. He instinctively tries to protect her from his boss’s unwanted advances. After Molly boards her flight, she soon discovers that she has left her cellphone behind. When her friend Patty calls the phone, it's Kirk who picks up. They arrange a spontaneous meeting for the following day at the Andy Warhol Museum, where Kirk can return her forgotten device.
The next evening, Kirk arrives at the museum with his friend Devon. Molly invites them to join the celebration, and as they mingle, a string of embarrassing incidents occur, culminating in Kirk accidentally spilling his drink on the esteemed museum director. Although he accepts full responsibility for the mishap, the director decides to kick them out. As they exit, Molly appears, clearly impressed by Kirk’s selflessness and offers him tickets to a Pittsburgh Penguins hockey game—a gesture he readily accepts.
During the game, Kirk is joined by his friend Stainer, and they meet up with Molly and her friend Patty. Excitement fills the air, and Patty whispers to Kirk that she believes Molly is indeed interested in him. As their relationship begins to blossom, Stainer warns Kirk that the glaring disparity between their "numbers"—a perfect 10 for Molly versus a mere 5 for Kirk—could derail their budding romance.
Meanwhile, Patty reveals her theory to Kirk that Molly might have picked him because he represents a safe option, unlikely to cause her any pain. Throughout a series of dates, the duo opens up about their dreams and aspirations. Kirk aspires to become a pilot, while Molly confesses that she once intended to pursue a career in law before discovering her real passion lay in event planning.
As the evening unfolds, Kirk and Molly share a tender kiss in his car, igniting a spark between them. Later, during a sunny family gathering, Molly captivates everyone with her charisma, leaving Marnie feeling jealous of the attention she garners. However, fate takes a sharp turn when Molly’s parents unexpectedly appear, catching Kirk off guard and leading to an awkward departure. Consequently, Molly is left questioning whether Kirk is intentionally trying to avoid her family. Despite his genuine apologies and promises to remedy the situation, Molly starts to create distance.
Days later, Kirk proposes an innocent idea of hosting a birthday party for Molly's sister Katie, but as the evening progresses, he grows increasingly unsettled with Molly’s vague answers about his job when speaking to her parents. The sudden return of Cam, her adventurous ex-boyfriend and an audacious stunt pilot, only deepens Kirk's insecurity. When they return to Molly's apartment, passionate moments are interrupted when Kirk discovers that Molly has webbed toes—a fact he thinks is trivial compared to her overall perfection.
Molly’s feelings are hurt, stemming from Kirk’s insecurities, which she believes are a result of her prior experiences with Cam. She reveals that she was initially drawn to Kirk because he seemed safe and reliable. This shocking admission causes Kirk to reassess their relationship, leading him to break up with Molly in favor of Marnie.
In the meantime, Stainer reflects on his own insecurities with past relationships and realizes he needs to make amends. He convinces Patty to bring Molly to the airport, setting the stage for a reunion between her and Kirk. Stainer’s audacious plan to halt a plane mid-air prompts everyone to disembark, and Kirk seizes this chance to reconcile with Molly, confessing his true feelings and apologizing for his previous insecurities.
In a display of newfound confidence, Kirk surprises Molly with a mystery trip to Cleveland on a small aircraft, revealing his long-held dream of being a pilot. As they glide through the skies, their love takes off once more, more resilient than ever.
