Directed by
David E. Talbert
Made by
Fox Searchlight Pictures
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.
Montana's Mother's Beliefs
Montana Moore is heavily influenced by her mother's fervent belief in marriage, despite her mother's numerous past unions. This foundation sets a complicated backdrop for Montana's own romantic pursuits, as she navigates her desires against a backdrop of familial expectations.
Letter from Graham
Montana receives a letter from her neighbor and friend Graham Jackson, inviting her to spend Thanksgiving in Chicago. This revelation ignites hope within Montana that this visit could lead to a proposal, as she shares her excitement with her flight attendant friends.
Gifts from Friends
Before her trip, Montana's friends provide her with gifts to enhance her love life. Sam gives her a necklace intended to attract true love, while Gail humorously includes cranberry-flavored condoms, symbolizing their support and playful camaraderie.
Romantic Evening with Graham
During her visit to Chicago, Montana and Graham share a night filled with romance, featuring a scenic boat ride and intimacy. However, it takes a turn when Graham leaves her at a hotel, claiming to have a business meeting, casting doubt on their relationship.
The Discovery
Concerned about Graham's whereabouts, Montana reaches out to Gail, who suspects Graham may not be faithful. In an act of courage, Montana sneaks to Graham's place only to find a pregnant woman arriving, forcing her to confront the painful truth of being the other woman.
Seeking Comfort from William
Struggling with heartache, Montana turns to her friend William for solace. He offers a comforting meal, providing her with a brief respite from her emotional turmoil as he tries to lift her spirits amid her heartbreak.
Sister's Engagement Announcement
Montana visits her family, where her sister Sheree announces her engagement. This news deepens Montana's anxiety about her single status, especially as her mother pressures her about marriage, intensifying her feelings of inadequacy.
Setting a Deadline
Feeling the pressure of her sister's impending wedding, Montana fabricates a timeline for herself, declaring she must find a husband within the next 30 days. This determination sets off a whirlwind of attempts to reconnect with past romantic interests.
Bumping into Exes
Montana enlists Sam's help in a plan to 'bump into' her exes during flights. Despite the risks, she embarks on this unconventional journey, hoping to reignite former flames and secure a potential partner before her sister's wedding.
Awkward Date with Damon
Montana's first reconnection is with Damon Diesel, who disappoints her by exhibiting immature behavior. The encounter crescendos to an embarrassing escape through a fire exit, reinforcing the setbacks in her search for love.
Meeting Langston
Next, Montana dates Langston, who is absorbed in his political ambitions. Their time together is riddled with condescension, leaving Montana yearning for genuine connection and pushing her to seek comfort in William's company instead.
Secret Encounter with William
Amidst her romantic mishaps, Montana shares a dreamlike and intimate moment with William, sparking a flicker of hope in her heart. This connection stands in stark contrast to her disheartening experiences with her exes.
Confronting Disappointment
Montana's journey continues to be fraught with frustration as she faces another dead-end in her quest for love. A chance encounter with William's girlfriend deepens her loneliness, making it increasingly difficult for her to find solace.
Sister's Rehearsal Dinner
Montana attends her sister's rehearsal dinner, where she plans to announce her own engagement. Instead, Langston surprises everyone by proposing to Sheree, prompting Montana to reflect on her own unattainable aspirations.
A New Understanding
In a moment of clarity, Montana publicly confronts her fears and desires, realizing she doesn't need marriage to validate her worth. This revelation prompts her mother to apologize, acknowledging her own regrets about love and societal expectations.
The Proposal
In a dramatic twist, Montana races to catch a flight to France armed with nostalgic ties to her childhood. Just when she fears she may have missed her chance, William confesses his love and proposes, culminating in a joyful moment that redefines her views on love.
Planning New Beginnings
As Montana's journey reaches a happy conclusion, she playfully schemes with her friends to set them up with potential partners. This lighthearted moment signifies a new chapter for her as she embraces the prospects of love and friendship.
Montana Moore
Montana is a flight attendant struggling with her romantic life and the pressures of societal expectations. Her determination to find love drives the plot, but she eventually learns to embrace her individuality.
William
William is Montana’s supportive friend who provides comfort during her tumultuous journey. He embodies the qualities of loyalty and emotional depth, ultimately revealing his own feelings for her.
Graham Jackson
Graham is the seemingly perfect love interest for Montana but ultimately disappoints her by revealing another commitment. His initial charm masks a lack of genuine investment in their relationship.
Gail
Gail is one of Montana's flight attendant friends, providing comic relief and support throughout the film. Her humorous nature highlights the importance of friendship during challenging times.
Sam
Sam serves as Montana’s loyal confidant, who concocts plans to help her reconnect with her past relationships. His well-meaning but misguided efforts illustrate the lengths friends will go to support each other.
Time period
While the specific time period is not explicitly stated, the modern-day setting is reflective of contemporary social dynamics around love and relationships. It presents a world where airport travel and online communication shape romantic encounters.
Location
Chicago, France
The movie prominently features Chicago, known for its iconic skyline and cultural diversity, as a destination for romantic aspirations. Additionally, France symbolizes love and adventure, serving as the backdrop for the pivotal flight that defines Montana's journey.
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Love
The central theme revolves around the quest for love and societal pressures pertaining to marriage. Montana's journey showcases her struggles with expectations and her ultimate realization that self-worth is not tied to marital status.
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Heartbreak
Throughout the film, Montana faces multiple heartbreaks that challenge her perception of love and trust. These experiences teach her valuable lessons about relationships and personal growth.
👰♀️
Marriage
The film examines the institution of marriage, especially influenced by Montana’s mother’s beliefs. It critiques the romantic idealism surrounding marriage while promoting the idea that love can exist outside conventional norms.
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