Say Anything... 1989

As the curtain closes on their senior year of high school, the unassuming yet endearing Lloyd Dobler (no surname necessary) sets his sights on the academic superstar Diane Court, despite their differing social circles. With no clear plan for his future, Lloyd resides with his sister Constance, a single mother, while Diane’s sheltered upbringing has her living with her doting father Jim, owner of a local retirement home where she also works.

As graduation approaches, Lloyd invites Diane to their joint party, a bold move that catches everyone off guard. Their next “date” takes them to Diane’s residence, where Lloyd’s attempts to impress Jim fall flat, and the Internal Revenue Service drops a bombshell: Jim is under investigation for alleged embezzlement. Amidst this chaos, Lloyd and Diane grow closer, sharing intimate moments and laughter with the retirement home residents.

Lloyd also becomes a driving force in Diane’s life, teaching her to master the manual transmission of her graduation gift, a Ford Tempo. As their bond strengthens, Corey, Lloyd’s musician friend still reeling from his cheating ex-girlfriend Joe’s betrayal, advises him to take care of Diane and not let Jim’s disapproval dictate their relationship.

However, Jim’s concerns prove well-founded as he urges Diane to end things with Lloyd, deeming him an unsuitable match. Diane, torn between her love for Lloyd and her studies, ultimately decides to prioritize the latter and ends their romance, leaving Lloyd heartbroken and seeking solace from Corey’s words of wisdom.

Meanwhile, Jim faces his own turmoil as the IRS investigation drags on, resulting in declined credit cards and mounting financial stress. In a poignant moment of vulnerability, Diane stands outside her bedroom window at dawn, serenaded by Lloyd’s boombox playing Peter Gabriel’s “In Your Eyes,” the same song that played during their intimate moments.

The next day, Diane confronts Jim about his embezzlement, only to discover cash concealed in their home. Jim justifies his actions as a means of providing financial independence for Diane and better care for his retirement home residents. Distraught but ultimately wiser, she reconciles with Lloyd at his kickboxing gym, where they rekindle their love amidst the uncertainty of their futures.

As the sweltering summer draws to a close, Jim’s world comes crashing down when he finds himself behind bars, serving out a nine-month sentence that will leave him feeling isolated and helpless. It’s during this bleak period that Lloyd pays a visit to his incarcerated friend, bearing news that will shatter Jim’s fragile sense of calm. With a mix of excitement and trepidation, Lloyd reveals that he’ll be embarking on an adventure across the pond with Diane (played by), leaving Jim feeling bitter and abandoned. In a bid to soften the blow, Lloyd produces a letter from Diane, its words serving as a poignant reminder of their complicated relationship.

But just as it seems like Jim is about to succumb to despair, the door swings open once more, this time admitting Diane herself. Her arrival sparks a flurry of emotions - sorrow, longing, and ultimately, a deep-seated connection that transcends the confines of their physical separation. As she prepares to depart for England, Diane imparts a small but significant token of her affection: a pen that had previously been passed from Lloyd’s hands to hers, now entrusted to Jim as a symbol of their enduring bond.

As Lloyd and Diane take to the skies, bound for a new chapter in their lives, he proves himself to be a stalwart companion, offering words of reassurance and comfort to the anxious woman by his side. Despite her fear of flying, Diane finds solace in Lloyd’s unwavering support, a testament to the strength that can emerge from even the most turbulent of relationships.