Lauren Reynolds, portrayed by Drew Barrymore, is a single mother juggling the responsibilities of raising her two sons, Brendan and Tyler. One fateful night, she meets Jim Friedman, a widower played by Adam Sandler, at a blind date set up at Hooters. Jim has three daughters—Hilary, Espen, and Lou—who are struggling to cope with the loss of their mother to cancer.
Lauren's previous marriage ended when her husband, Mark, expertly played by Joel McHale, cheated on her. Though she never disclosed the truth to her boys, Brendan and Tyler harbor resentment towards her dating, believing it betrays their family's history. Her profession as a closet organizer seems trifling compared to the emotional disarray surrounding her.
While she is out on her disastrous date, Lauren entrusts her sons to a babysitter, Tracy, who inadvertently becomes involved in their chaotic antics. Their return home is marked by disaster as Jim's laid-back, careless approach clashes with Lauren's perfectionist tendencies. In an awkward moment, Jim consumed her beer and was more keen on watching sports than engaging with Lauren. The date escalates further when Jim, pretending there’s an emergency, leaves, leaving only a measly $20 for his part of the bill.
Amongst the comedy, we see the genuine struggles of parenthood. Lauren seeks assistance from her supportive friend Jen, played by Wendi McLendon-Covey, who urges her to embrace her femininity and confidence. The humorous dynamics in Jim's family are revealed, with Hilary dressing as a tomboy and claiming she can speak with her deceased mother, while Espen openly struggles with the idea of moving on.
In a twist of fate, Jim and Lauren serendipitously bump into one another at a pharmacy while shopping for items intended for their children. Their interactions are laced with banter, and they accidentally switch credit cards, spurring on more misadventures. Their unknowing arrangements for the same family vacation in Africa culminate in a delightful yet awkward reunion.
As both families navigate their shared experience under the guidance of charismatic hotel staff like Terry Crews, the bonds between children and parents gradually strengthen. The kids initially embarrassingly meet, with Brendan teasingly calling his mother "hot" and Hilary struggling to be accepted by her crush, Jake, the son of another couple, played by Kevin Nealon.
Through a comedic series of events filled with heartfelt moments, Jim bonds with Lauren's boys over sports, while Lauren assists Jim’s daughters in embracing their individuality and femininity. As they journey through the vacation, feelings evolve, and the barriers separating Jim and Lauren begin to erode. During a touching moment, Lauren unknowingly sings "Over the Rainbow" to Lou, a sentimental gesture that reveals her growing affection towards the girls.
Their romance blooms against the backdrop of beautiful shared experiences, concluding with a romantic dinner where Jim hesitates to embrace his feelings. However, upon returning home, Jim realizes he has fallen for Lauren. After a series of misunderstandings with her ex, he decides to pursue her once more.
The culmination of their journey leads to an inspiring moment at Tyler's baseball game, where, amidst support from family and friends, Jim and Lauren confess their love for one another, culminating in a joyful kiss that promises a brighter future for blended families.
