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.
