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Tim thinks he’s invited the woman of his dreams on a work retreat to Hawaii, realizing too late he mistakenly texted someone from a nightmare blind date.
In Portland, Tim has a blind date with Melissa, nicknamed Missy, who turns out to be extremely strange, and her oddball behavior turns out to be both dangerous and disastrous. Her wild antics force Tim to sneak out of the restaurant through a bathroom window, thereby dislocating his ankle.
Three months later, Tim bumps into a beautiful and successful woman (also named Melissa) at the airport. They connect over drinks, finding out they have nearly everything in common and seem to be perfect for each other. She gives him her number.
After a series of intimate texts, he eventually invites Melissa to his work retreat in Hawaii. However, Missy shows up on the plane, and Tim realizes he had been texting the wrong Melissa the whole time. The antics start again as Missy forcibly gives him a tranquilizer and, when he awakens, she is giving him a handjob.
On the corporate retreat in Hawaii, the new CEO, Jack Winstone, greets everyone at the welcome party. When Missy makes an appearance, she is awkward and wild, and seems to always leave Tim in embarrassing situations in front of his boss and colleagues. Back at their room, he awakens from another tranquilized state to her on top of him, riding him cowgirl style. She often becomes reckless and intoxicated and her behavior humiliates Tim.
However, before too long, Missy starts to help Tim succeed at his work retreat, and even hypnotizes his boss to win his favor. As they spend more time together, Tim eventually begins to fall for her. His workplace competitor, Jess “the Barracuda”, is not pleased when Winstone gives a job to Tim instead of her, so she reveals to Missy that her invitation was a mistake, and Tim had wanted to bring someone else. When Missy checks Tim’s phone, she finds out the truth. Saddened and devastated, she leaves Hawaii.
However, at the moment Missy leaves in a cab, the actual Melissa arrives in Hawaii (having been invited by Jess). At lunch, Tim begins acting outlandishly, much like Missy did on their first date, imbibing a bevy of alcoholic shots and then performing a walking handstand in the dining room. After falling from the balcony and crippling himself, Tim lets the new Melissa know that he has developed feelings for Missy, and then departs Hawaii. Back in the office, Tim decides to remove the hypnotic spell Missy put on his boss by uttering the obscene and obscure magic words. His honesty results in him losing his job.
Tim tricks Missy into a date, where he plays the same trick that she had used on him. Except she meets Vanilla Ice at the bar. Tim comes up and apologizes to her and tells her he used to want someone exactly like him, but now realizes he does not. He tells her all the things that he likes about her, and says that he wants to be more like her. She forgives him, and they kiss.
English