In a life that echoes the tropes of romantic comedies, Elliot, portrayed by the talented Peter Dinklage, finds himself on the brink of marriage with his girlfriend, Caroline Swann. As their wedding day looms closer, the unsettling presence of Caroline's former boyfriend, Bradley, casts a shadow of doubt over their relationship. The very thought of Caroline's unresolved feelings for this ghost from her past sends Elliot spiraling into a whirlwind of anxiety.
In his quest to maintain his composure, Elliot encounters Cecil, a vibrant and captivating temp at his accounting firm, whose charm and unorthodox insights act as a soothing balm for his frazzled state of mind. Her infectious optimism offers a glimpse of hope in Elliot's otherwise bleak outlook, igniting a series of events that push him to reevaluate his own identity and the world surrounding him.
As his interactions with Cecil deepen, Elliot begins to appreciate her spirited enthusiasm and artistic flair. They bond over their mutual love for music, and Cecil shares her dream of becoming a singer-songwriter during an intimate performance at a nearby club. Her encouraging words – urging Elliot to embrace life and take bold risks – resonate profoundly, igniting a growing dissatisfaction within him regarding his mundane life.
The return of Caroline only intensifies Elliot's turmoil. A spontaneous decision to let Cecil stay with him after a chaotic night leads to an uncomfortable run-in with their wedding planner, which spirals into a comedy of errors and ultimately results in Caroline calling off their wedding.
As Elliot grapples with the disintegration of his plans, he must confront the uncomfortable truths about his own stagnation. A chance meeting with Dan, Cecil’s unsupportive boyfriend, alongside Sonya, Bradley’s current partner, serves as a sobering reminder of the plight of the "nice guy" who perpetually finishes last. This confrontation propels Elliot into a moment of existential reflection, casting doubt on his future.
In an unexpected twist, Louis, Caroline's brother-in-law, offers Elliot a potential second chance to rekindle his engagement. While navigating his own feelings amidst uncertainty, Elliot tries to reconcile his desires with the unpredictable nature of love.
Just as Elliot's well-orchestrated romantic evening with Caroline is about to unravel, he discovers her tenderly comforting Bradley, who has just split from Sonya and is reigniting old sparks with Caroline. After some persuasion from Caroline, Elliot begrudgingly agrees to include Bradley in their evening plans, resulting in a shift from upscale dining to a casual burger joint that Bradley frequents. In this unfamiliar setting, Elliot confides his worries to Cecil over the phone.
The following day at work brings another surprise; Cecil is back, fulfilling her temp duties and inviting Elliot for drinks. As they share their thoughts, Elliot narrates how, contrary to Caroline's belief in his lack of romance, he surprised her with a spontaneous dance at their last gathering. Meanwhile, Bradley's impressive breakdancing inadvertently disrupts Elliot, leading to Caroline’s concern. All the while, Elliot reveals his impending assignment to Malta focused on geodes.
While Cecil absorbs his words, her own feelings for Elliot grow stronger, particularly as she hints at Dan's upcoming move to Cincinnati, which visibly unsettles Elliot.
Fast-forwarding to the wedding ceremony, the atmosphere shifts dramatically when Bradley crashes the event, publicly proclaiming his love for Caroline just as Elliot prepares to voice his own feelings. Overwhelmed, Caroline succumbs to her emotions, sharing an impassioned kiss with Bradley before Elliot bolts from the scene, desperately racing to catch Cecil before she leaves town. He arrives at her apartment just as Dan exits, mustering the courage to confess his feelings for Cecil and instinctively chasing off an old acquaintance.
As everything settles, Elliot and Cecil reunite on stage at the same club where their love story began, with Cecil performing one of her signature songs while Elliot plays the piano. In a reflective post-credits scene, Dan contemplates his own status as a classic "Baxter," having just lost the love of his life to the story's protagonist.
