Flight attendant Montana Moore (Paula Patton) has always felt the weight of her mother's (played by Jenifer Lewis) fervent belief in the sanctity of marriage, especially considering her mother's many past unions. Sadly, Montana's romantic endeavors have not mirrored that ideal. She has practical expectations for a partner—he must be faithful, prioritizing her over work, be easygoing, and financially secure—but deep down, her greatest fear is being alone.
Recently, Montana believes she has found potential happiness in Graham Jackson ([Boris Kodjoe]). Her neighbor and friend William (Derek Luke) reveals that Graham has sent her a letter inviting her to spend Thanksgiving in Chicago, igniting hopes that this could be the moment Graham proposes. She shares her excitement with her fellow flight attendants, the playful Gail (Jill Scott) and her loyal friend Sam (Adam Brody). Before embarking on her trip, Sam gifts Montana a necklace meant to attract true love, while Gail hilariously includes cranberry-flavored condoms.
Montana and Graham share what seems to be a romantic evening, including a boat ride and intimacy. However, to her dismay, he leaves her at a hotel, claiming he has a business meeting. Concerned, she calls Gail, who suspects there may be another woman in the picture. In a moment of misguided courage, Montana sneaks over to Graham’s place, only to discover a pregnant woman arriving, leading her to realize she was merely the other woman. Heartbroken, Montana departs.
Feeling despondent, she turns to William, who attempts to lift her spirits by preparing a comforting meal. A visit to her family yields further complications as her sister Sheree ([Lauren London]) announces her engagement—something that leaves Montana feeling increasingly anxious about her own solitary status, especially as her mother champions marriage. Desperate not to appear single at her sister’s wedding, Montana sets a timeline: she has to find a husband within the next 30 days.
Sam suggests a scheme to "bump into" her exes on flights, using their inside knowledge of airline schedules. Despite Gail’s concerns about the legality of their plan, Montana sets off to reconnect with her past suitors. Her first encounter is with Damon Diesel ([Trey Songz]), who turns out to be less than ideal as he’s living off a co-worker and ends their time together in an embarrassing escape through a fire escape.
Next, she meets Langston ([Taye Diggs]), who is running for Congress. However, an awkward date filled with condescension pushes Montana further away, leading her to seek solace in William’s company. They share an intimate yet dreamlike encounter, which keeps the idea of romance alive in Montana's heart, despite the turmoil around her.
As the days pass, Montana's search for love leads her through a string of disappointing reconnections, amplifying her frustration. One night, she inadvertently discovers William's girlfriend Taylor ([Christina Milian]), who begs her to keep their relationship's fragility under wraps, exacerbating Montana’s feelings of betrayal and solitude.
An unexpected encounter with Quentin ([Djimon Hounsou]) does not offer the solution either; he openly expresses his aversion to marriage, leaving Montana more disheartened than before. After another tumultuous evening, including a rude confrontation with William, Montana attends her sister’s rehearsal dinner with the intention of announcing her own engagement. Instead, Langston surprises everyone with a proposal to her sister, offering a moment for Montana to reflect on her own desires.
In a heartfelt moment, Montana publicly confronts her fears, declaring her journey has taught her that she does not need a marriage to define her worth. This moves Catherine, her mother, to apologize for her pressuring tendencies, sharing her own regrets about love and life.
The film culminates in a whimsical race against time as Montana rushes to catch a flight to France, carrying a box of Cracker Jacks from William, which holds a nostalgic note from their childhood. Just as she thinks she has missed her chance, William fervently expresses his love and proposes for real, leading to a joyful climax that redefines her outlook on love.
As her journey concludes, Montana playfully schemes with her friends, setting them up with potential partners, marking the film's end with the promise of new beginnings.
