im has a blind date with Melissa, nicknamed Missy. Missy is extremely strange, and her odd behavior turns out to be disastrous for Tim. Her wild antics result in Tim sneaking out of the restaurant through a window and subsequently dislocating his ankle.
Three months later, Tim meets a beautiful woman, also named Melissa, at an airport. They connect with much in common and seem to be perfect for each other. She ends up giving him her number. He begins texting her and eventually invites her to his work retreat in Hawaii. However, on the plane, Missy shows up, and Tim realizes he had been texting the wrong Melissa. Missy drugs Tim, forcibly giving him a tranquilizer and he awakens later on the plane to her giving him a nonconsensual handjob.
In Hawaii, Jack Winstone, the new CEO, welcomes everyone. Missy is awkward and wild and always seems to end up leaving Tim in embarrassing situations in front of his boss and colleagues. At the hotel, he awakens to her on top of him, having nonconsensual sex with him in his sleep. She often becomes reckless and intoxicated and her behavior results in humiliation for Tim. However, as time goes on, she starts to help Tim do well at his work retreat and also wins Winstone’s favor towards Tim by hypnotizing him. Tim eventually begins to fall for her. Tim’s workplace competitor, Jess, is not pleased with Winstone giving a job to Tim instead of her. So Jess reveals to Missy that she was invited there by accident and wasn’t the one Tim wanted to invite. Missy checks Tim’s phone and finds out the truth. Saddened and devastated, she leaves Hawaii.
Meanwhile, the actual Melissa arrives in Hawaii, having been invited by Jess. At lunch, Tim begins acting much like Missy did on their first date, taking multiple shots and performing a handstand in the diner. Tim lets her know that he has feelings for someone else and leaves Hawaii for Portland. Tim also removes the hypnotism Missy put on Winstone, and Winstone ends up firing him.
Tim meets with Missy and he apologizes and tells her all the things that he likes about her and that he wants to be more like her. She forgives him, and they kiss.
In a mid-credits sequence, Komante, a guide from the retreat, attempts to row a co-worker of Tim’s, having developed a fear of flying from a psychic reading Missy gave him, to Portland in the middle of the ocean.