On a flight from New York to Los Angeles, twelve-year-old Ryan Walker, played by Brendon Ryan Barrett, finds himself seated next to a girl named Jennifer, portrayed by Raquel Beaudene. Their conversation revolves around the challenges of their parents' divorces, but it quickly escalates into an argument. Fast forward four years, at Harding High School, the now-adult Jennifer has been crowned homecoming queen while Ryan, played by Freddie Prinze Jr., embarrassingly stumbles as the team mascot. When they finally speak, Jennifer recognizes him from the flight and invites him for coffee, but a disagreement leads Ryan to turn her down.
Later, Ryan embarks on his college journey at Berkeley, sharing a dorm with the wildly flirtatious and notorious liar, Hunter, played by Jason Biggs. Meanwhile, Ryan is struggling to maintain a long-distance relationship with his high school girlfriend, which ultimately fails. Interestingly, it turns out Jennifer is also enrolled at Berkeley. After her boyfriend breaks up with her in the form of a song, she moves in with her friend Amy, played by Amanda Detmer, who often discusses her therapist. As Ryan and Jennifer reconnect to share their breakup experiences, tension reignites between them.
A year later, Ryan is dating Amy, only to discover Jennifer waiting to end the relationship on Amy's behalf. In a comedic twist of fate, Ryan's attempts to convince Amy of their compatibility lead to a mishap involving icy balm, resulting in a day spent with Jennifer. He expresses his desire to avoid relationships due to their uncertainty, contrasting with Jennifer's preference for spontaneity.
When school resumes after summer, Jennifer opens up to Ryan about a painful summer fling, leading her to tears. Their friendship deepens as they share lively outings in San Francisco, including a memorable night of dancing. However, when asked if she has feelings for Ryan, Jennifer hesitantly denies it, reflecting his own hesitation when Hunter inquires about his feelings. The situation becomes more complicated as Ryan begins dating another girl, Megan, played by Heather Donahue. Tensions rise when Jennifer finds herself troubled by men and delivers an emotional speech about love in a café, which unexpectedly culminates in them sharing a kiss and spending the night together.
The following day, the air grows tense between Ryan and Jennifer as they grapple with their feelings, ultimately deciding their encounter was a mistake. However, Ryan's withdrawal from her persists until the day Jennifer prepares to leave for Italy. Their confrontation leads to Ryan admitting he believes they are meant to be, despite his lack of a plan, causing Jennifer to realize their connection holds deeper significance.
As the day of her departure approaches, Jennifer boards a bus bound for the airport, only for fate to intervene as she witnesses Amy and Hunter (now calling himself Steve) connecting at the bus stop. In a moment of clarity, she instructs the bus driver to halt mid-journey across the Golden Gate Bridge and returns to Berkeley, where she learns from Hunter that Ryan has already departed for LA. Just as Ryan is about to take off on his flight, Jennifer bursts onto the plane to declare her love, sparking yet another argument. Ultimately, she convinces him, culminating in a passionate kiss as the plane takes off into the sky, symbolizing a new beginning for the two.
