In a picturesque coastal retreat nestled in Rhode Island, we meet Dan Burns, a widowed father and newspaper advice columnist, who finds himself entangled in a complicated web of relationships. As Dan navigates the choppy emotional waters of his life, his family convenes for their annual gathering at their parents' home. Among them are his siblings, Mitch, with his carefree spirit, and his sister, each bringing along their families for the joyous occasion.
The morning following their arrival brings an unexpected twist when Dan encounters Marie in a cozy bookshop. They strike up a delightful conversation over muffins, despite Marie's reminder that she’s already committed to someone else. When Dan returns to his family's gathering and shares this revelation, the entire family enthusiastically encourages him to pursue a relationship with Marie.
However, Dan's plans take a sharp turn when Mitch introduces his new girlfriend—much to Dan's shock, it’s none other than Marie herself. Heartbroken and dejected, Dan grapples with the well-meaning but frustrating advice from his father to follow the same romantic path. Rather than sulking, he begrudgingly agrees to join a double date with his childhood friend, Ruthie "Pig Face" Draper, which only deepens Marie's discomfort as she watches this unfold.
As the simmering tension between Dan and Marie escalates during family interactions, Dan finds solace in late-night outings with Ruthie. The awkwardness intensifies when Marie delivers a silent treatment punishment the following morning, leaving Dan to struggle through a meal of burnt pancakes in unbearable silence.
With a family talent show on the horizon, Dan dodges participation until Mitch persuades him to join in a musical number. During their rendition of "Let My Love Open the Door," Dan’s heartfelt singing appears to reach out directly to Marie. Yet, the following morning sees Marie ending her relationship with Mitch and leaving, leaving Dan bewildered.
Just when things seem bleak, Marie contacts Dan, leading to an unexpected date at a bowling alley amidst a downpour of rain. Their connection ignites, resulting in a passionate kiss—only to be interrupted by a furious Mitch, who confronts Dan, leading to a physical altercation. Meanwhile, Dan's middle daughter, Cara, is increasingly frustrated by her father's interference in her own relationship, a love she cherishes deeply for Marty's sake.
As the consequences of the chaotic bowling alley incident unfold, Dan's relationships with his three daughters come under immense strain. The atmosphere is charged as they confront their anger and hurt towards him. Yet, determined to mend fences, Dan takes the initiative to reconcile, fostering a renewed sense of family unity. Their journey culminates in a trip to the vibrant streets of New York City, where they track down Marie at her gym. In a heartwarming moment full of realization, Dan locks eyes with Marie and, through a poignant voice-over, shares insights from his advice column, urging against excessive planning and promoting the beauty of life's unexpected moments.
As the credits begin to roll, we see Dan and Marie standing together, hand in hand, as they exchange vows at Dan's parents' Rhode Island estate, surrounded by loved ones in an atmosphere thick with joy and celebration. The scene is uplifted by Mitch and Ruthie dancing in bliss, while Cara and Marty share a heartfelt waltz—the essence of acceptance and happiness radiating in every corner of this magical celebration.
