Directed by
Tyler Spindel
Made by
Netflix
Tim, played by David Spade, finds himself in a truly chaotic situation when he goes on a blind date with a woman named Melissa, humorously referred to as Missy, portrayed by Lauren Lapkus. From the very beginning, their date takes a nosedive when Missy, in a wild attempt to break the ice, causes a scene at the bar by confronting a man hitting on another pregnant woman. This outlandish behavior leads Tim to make a dramatic escape through a window, which results in him dislocating his ankle.
Fast forward three months, Tim’s workplace, Credit Of America, is undergoing a major merger, stirring up a host of complications in his life. At this critical moment, he encounters another Melissa, played by Molly Sims, at the airport. This new connection appears perfect, as they share similar interests and lifestyles, including a mutual aversion to drinking. Tim is ecstatic when she gives him her number, but his excitement is cut short when Missy unexpectedly re-enters his life on a flight to Hawaii.
“I was about to jump off a bridge when I got your text!” Missy humorously states, easing any immediate concern Tim may have thought he had regarding her well-being.
Missy’s antics escalate as she forcibly tranquilizes Tim on the flight and then exhibits bizarre behavior, such as gatecrashing a shark tank dive led by Rob Schneider, who portrays Komante, a somewhat eccentric guide. The lunacy doesn’t stop there; throughout the company retreat, Tim’s attempts to maintain professionalism are continually sabotaged by Missy’s unpredictable and oftentimes reckless behavior, including mistakenly trying to jump off a cliff and an incident involving a sea turtle.
While Tim grapples with the chaos Missy brings into his life at work, he also has to manage the fact that his ex-fiancée, Sarah Chalke, is now dating his colleague Rich, played by Chris Witaske. As Missy and Tim’s outrageous escapades unfold, including a wild talent show where underwhelming performances surprisingly garner managerial praise, Tim starts to see a different side of Missy that he can’t help but appreciate.
Unfortunately, jealousy rears its head when Tim’s competitor, Jess, played by Jackie Sandler, reveals the truth about which Melissa Tim was trying to date all along. This revelation leads Missy to feel betrayed and hurt, prompting her to leave Hawaii, while Tim’s crush on her deepens.
In a heartfelt climax, the actual Melissa arrives, while Tim experiences a moment of self-realization, deciding to distance himself from the life he was leading. After quitting his job and mending his relationship with Missy through a sincere apology, he finally expresses the admiration he has developed for her, leading to a sweet kiss that signifies their evolving relationship.
Blind Date Gone Awry
Tim goes on a blind date with a woman named Melissa, affectionately called Missy. The date spirals out of control when Missy confronts a man who is bothering a pregnant woman, causing a scene and forcing Tim to escape through a window, ultimately dislocating his ankle.
Three Months Later: Merger Chaos
After three months, Tim is faced with turmoil at his workplace due to a major merger happening at Credit Of America. This stressful situation adds to his personal life complications, setting the stage for new encounters.
Perfect Connection at the Airport
While at the airport, Tim meets another woman named Melissa, who seems to be his ideal match. Their shared interests and lifestyle make Tim excited about the potential of a new relationship, especially when she gives him her number.
Missy Returns
Just as Tim is enjoying his new connection with Melissa, Missy unexpectedly appears on the same flight to Hawaii. Her comical statement about almost jumping off a bridge lightens the mood but sets the stage for more chaos.
Tranquilized on the Flight
Things take an absurd turn when Missy tranquilizes Tim during the flight. This bizarre behavior foreshadows the chaotic adventures that await them once they land in Hawaii.
Shark Tank Madness
After landing in Hawaii, Missy gatecrashes a shark tank dive led by Komante, an eccentric guide played by Rob Schneider. Her unpredictable antics continue to disrupt the retreat and embarrass Tim.
Company Retreat Sabotage
During the company retreat, Tim's attempts to act professionally are continuously thwarted by Missy’s reckless behavior. Whether it’s trying to jump off a cliff or causing chaos around a sea turtle, Tim's patience is tested.
Facing Jealousy
Tim struggles with jealousy as he learns that his ex-fiancée is now dating his colleague, Rich. This complication adds emotional depth to his chaotic relationship with Missy as they navigate their affection for one another.
Unexpected Revelations
Tim’s competitor Jess exposes his intentions concerning the two Melissas. This revelation deeply hurts Missy, who feels betrayed, leading her to distance herself from Tim as he contemplates his feelings.
Melissa's Arrival
The actual Melissa arrives in Hawaii, complicating everything for Tim. Amidst the confusion, Tim starts realizing that his feelings for Missy might just be stronger than he initially thought.
Tim's Self-Realization
In a moment of clarity, Tim decides to leave his old life behind. He recognizes the value of what Missy has brought into his life and resolves to make amends.
The Apology
Tim apologizes sincerely to Missy for the chaos and confusion that has transpired. This heartfelt moment allows them to reconnect and express their true feelings.
A Sweet Kiss
The timeline culminates with Tim and Missy sharing a sweet kiss, symbolizing their evolving relationship. This moment marks the transition from chaos to a more loving and understanding connection.
Tim Morris (David Spade)
Tim is a man caught in a whirlwind of romantic chaos, initially seeking a perfect relationship. He embodies a mix of ambition and vulnerability, struggling with the unpredictable nature of Missy's personality while also dealing with workplace pressures. As the story evolves, Tim's character undergoes significant growth as he learns to embrace love and spontaneity.
Missy (Lauren Lapkus)
Missy is the unpredictable and wild romantic interest who brings chaos into Tim's life. Her outrageous actions, from confronting strangers to unexpected antics at the company retreat, showcase her eccentric personality. Beneath the hilarity, Missy reveals a deeper side, prompting both Tim and the audience to appreciate her uniqueness.
Melissa (Molly Sims)
Melissa is introduced as Tim's initial ideal partner, perfectly aligning with his lifestyle. However, her role highlights the theme of how surface-level connections often fall short. She serves as a contrast to Missy, prompting Tim to reconsider what he truly desires in a relationship.
Jess (Jackie Sandler)
Jess is portrayed as Tim's competitor and ex-fiancée, adding layers of tension and jealousy to the narrative. Her presence serves as a catalyst for Tim's self-reflection and ultimately helps him realize what he values most. Jess embodies the complexity of past relationships that can influence new romances.
Time period
The events unfold in contemporary times, reflecting modern social dynamics and work culture. It explores the challenges of navigating personal relationships during significant life changes, such as workplace mergers. The characters are relatable, facing issues like jealousy, self-discovery, and the comedic chaos of romantic entanglements.
Location
Hawaii, Airport, Credit Of America
The movie takes place in various vibrant locations, starting with the chaos of an airport where Tim meets two Melissas. The beautiful backdrop of Hawaii serves as the primary setting for a company retreat, filled with amusing mishaps, including shark tank dives. Additionally, the high-stakes environment of Credit Of America adds a layer of tension as Tim navigates his professional life while dealing with personal drama.
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Love
The evolving relationship between Tim and Missy centers around the theme of love and acceptance. Despite the initial chaos and misunderstandings, Tim finds himself attracted to Missy's unique personality. The movie emphasizes how love can develop in unexpected circumstances and the importance of recognizing true feelings.
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Comedy
The film is rich with comedic elements driven by Missy's outrageous behavior and Tim's reactions to her antics. From wild scenes at the airport to bizarre escapades in Hawaii, the humor unfolds in a chaotic yet entertaining manner. It highlights how laughter can emerge from uncomfortable situations.
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Jealousy
Jealousy plays a significant role in the plot, particularly as Tim grapples with his feelings for Missy and the reappearance of his ex-fiancée, Julia, who is now dating his colleague. This emotional turmoil fuels the narrative, leading to moments of introspection and growth for Tim.
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