NOTE: This spoiler was written by Priya. who says, "This movie is a sweet, funny, romantic comedy about an incredibly dorky-looking guy (Kirk) who can't, for the life of him, figure out why he's attracted the attention and affection of a stunningly hot woman (Molly).
The movie opens to show the details of Kirk's life. He works a dead-end job at the airport, as a security officer in the baggage scanning area. After work, he goes home and tries desperately to get back together with his ex-girlfriend Marnie. He gives her a cheesy, heart-shaped, silver jewelry box with a picture of them on it. She thanks him for caring and comments on how nice his family has been to her, and how they've taken her in as one of their own. That's when you realize that she's hanging out with her new boyfriend at Kirk's parents' house, making it even more awkward for him to be there. He leaves absolutely dejected.
The next day, Kirk is back at work. A car pulls up and in slow motion, a pair of long, beautiful legs come out of the open door. A woman (Molly) with long, flowing blonde hair gathers her luggage and makes her way to the security checkpoint, attracting the attention of every male she passes. Kirk's sleazy supervisor begins hassling her and informs her that he needs to perform a strip-search on her. He falsely sets off his metal detector, but Kirk calls him out and tells him to let Molly through. Molly thanks him and runs off for her flight. It's only after she's seated on her plane that she realizes she's lost her iPhone. She asks her friend to call it. Turns out, the phone was left in a bin at the security checkpoint and Kirk answers it. Since the plane is already taking off, she tells him that she'll be back in town the following day, and that she'll meet up with him then.
The next night, Kirk and his friend go to meet Molly to give her back her phone. She asks him to meet her at an upscale party, an event that she put together, since she's a high-profile event planner. Molly asks Kirk and his friend to stay and have a few drinks, but they end up getting kicked out after talking back to the head of the museum where the party is held. Molly follows him out and apologizes, and then offers Kirk hockey tickets to tomorrow night's game as a thank-you for returning her phone. Kirk is pleasantly surprised and stammers that he'd love to go. She tells him she'll leave two tickets at will-call.
The next night, Kirk and his friend Stainer go to the hockey game. Kirk thinks that Molly is going to try to set him up with her friend Patty, so when Molly and Stainer go to get beer, he and Patty talk. He tells Patty that he's not really into her, but Patty clarifies that he's there for Molly, and that Molly's into him. Kirk's in absolute disbelief about the idea, because he thinks she's so out of his league.
The following day, Kirk discusses the situation with his friends, who are also in disbelief. They make up a scale, and tell Kirk that he's at best a 5, while Molly is a hard 10. They have no idea why she'd be interested in Kirk, which does nothing for his confidence. Meanwhile, Molly is shopping with Patty. Patty points out that Kirk is nothing like the other guys Molly has dated and asks if she's only dating him because he's safe. Molly says that although that's part of the reason, she also really likes Kirk, and that he's sweet and funny. That being said, Molly calls Kirk and asks him out to dinner.
They go out to a nice restaurant. Kirk is wearing a maroon blazer, and after a while realizes that all the waiters are wearing the same thing. He stammers awkwardly through dinner, until Molly asks him if he's nervous. He admits he is. A group of people walk by, and one of them, a really good-looking guy named Cam, stops and says hello to Molly. Kirk asks how they know each other, and Cam says they used to date. This makes Kirk feel even less confident about himself and more conscientious about how out -of-place he must look next to Molly. After dinner, he and Molly walk around and talk about themselves and their lives. She tells him that she completed law school, but decided that she didn't want to be a lawyer, so she made a career transition into event planning. Kirk drops her back to her apartment in his dumpy Dodge Neon. He helps her unstick her seatbelt and she kisses him goodnight.
The following day, he mentions to Molly that he's having lunch with his family. Molly asks to go along. Kirk's parents can't conceal their surprise over how gorgeous Molly is. Kirk takes her into the backyard to meet his brother, brother's girlfriend, Marnie, and Marnie's boyfriend. The men's jaws also drop, and Marnie can hardly hide her jealousy. The men invite Molly in for a swim, telling her that underwear is acceptable to swim in, since she hadn't brought a swimsuit. However, Molly informs them that she isn't wearing any underwear. During lunch, Marnie comes out in a trashy-looking dress and way too much makeup. She loudly whispers that she isn't wearing any underwear. Kirk seems embarrassed that he used to date her, which just rattles her more.
That night, Molly invites Kirk upstairs when he drops her off. They start making out on the sofa, and Molly ends up in his lap, grinding against him. Just when things get really hot and heavy, the doorbell rings and Molly jumps up to go answer it. Unfortunately, Kirk had gotten so worked up that he, well... finished into his pants. Even more unfortunately, it's Molly's parents and sister at the door. They come in, and Kirk is desperately attempting to hide the stain on his pants. Molly's father tries to shake Kirk's hand, but Kirk refuses to get up and do it. He finally awkwardly jumps over the back of the sofa and sprints out the door, looking horribly awkward and coming across as extremely rude to Molly's family.
His friends tease him ruthlessly the next day. They ask how many times he's called Molly, and he answers 17. No calls back. He goes to an outdoor aviation event that Molly is working at. He once again runs into her gorgeous ex Cam, who's a pilot, and who thinks Kirk is Molly's gay bff and informs him that he vows to win back Molly. He asks Kirk to put in a good word for him. Kirk finds Molly and apologizes for the other night, but she's upset and tells him that her family is very traditional, and that he made a horrible impression. He walks away sadly, but then walks back and tells Molly that she's incredibly hot, it had been a long time, and that he ejaculated prematurely into his pants and simply could not stand up and socialize with her family under the circumstances. He walks away, and after a few moments, Molly runs after him and hugs and kisses him.
That night, everyone is having drinks at a nightclub. Kirk finds himself next to Cam, who tells him that Molly told him that she was dating Kirk. He apologizes for thinking Kirk was gay. He also mentions Molly's defect and says that although it freaked him out initially, he eventually got over it. He also says that Molly hates being called perfect. Kirk asks him to elaborate on the defect, but Cam says he'll just have to find out on his own. Just then, Molly's parents arrive at the club and she re-introduces them to Kirk. Kirk makes a much better impression this time and they all have a wonderful night together. Later, once he and Molly are back at her place, they start getting down again. Kirk gets increasingly self-conscious as more and more clothing comes off. Molly is looking stunning in black lingerie, while he looks skinny, pale, and out-of-shape. Molly senses his discomfort and offers to tell him something she's self-conscious about if it'll make him feel better. He agrees and she shows him her toes. They're webbed! Kirk is visibly relieved. He can't believe that that's all it is! It's small and hardly noticeable. He was expecting something far worse. He goes on a rant and demands to know why she's dating him. He hurls out all the things he's been hearing from his friends, including his score of 5 and her score of 10. Molly tells him to just accept the fact that she likes him. She tells him not to put her on a pedestal because it's what all her exes in the past have done and she cannot possibly live up to it. The fight continues, they break up, and Kirk leaves.
Kirk is miserable, but tries to move on. He gets back together with Marnie and is seen boarding a plane with her and the rest of his family for a family trip to Branson. His friend Stainer feels bad about the breakup and realizes that it was all the horrible things Kirk's friends were saying that helped attribute to his breakup with Molly. Stainer calls Patty and convinces her to bring Molly to the airport.
Meanwhile, Kirk gets a call from Stainer who tells him he's making a huge mistake. Kirk tells off his family, breaks up with Marnie, and gets up to leave, only to be told by the attendant that the plane is taxiing, and that he cannot get off now. He quietly sits back down next to a glaring Marnie. Stainer gets a friend to call in a bomb threat, so the plane does get stopped.
Kirk runs off the plane and jumps onto a luggage cart. Marnie jumps on behind him and begins screaming and hitting him. He pushes her off and continues making his way through the airport until he gets to Molly. They apologize to each other and kiss and make up.
The last scene shows Molly walking to a small plane with her luggage, as she and Kirk are going on a trip. Kirk jumps into the pilot's seat and reveals that he got his pilot's license and that he'll be flying them. They take off into the sunset.
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