Lindsay is stuck in the middle of her relationship with Ben and his passion for the Boston Red Sox.
When relaxed and charming Ben Wrightman meets workaholic Lindsey Meeks she finds him sweet and charming, they hit it off and when it is winter Ben can spend every waking hour with Lindsey, but when summer comes around the corner Lindsey discovers Ben's obsession with the Boston Red Sox. She thinks it is perfect until everything goes downhill for them.—Drew-Barrymore-Fanatic
According to Boston Red Sox super fan Ben Wrightman, finding romance is just as likely as his beloved team winning the World Series. But then Ben meets Lyndsey Meeks, and suddenly anything's possible. Well... until Spring Training begins, and Lindsey sees Ben on ESPN in Florida acting like an idiot. But these games don't count, and she knows that there may be trouble once the first pitch is thrown. But she seems fine about it, because as she competes for a promotion, she says Ben won't be affected by her at work all the time. But things really get out of hand when Lyndsey gets hit by a line drive foul ball off of Baltimore Orioles' Miguel Tejada, and the Sox begin to loose. The relationship picks up, but when Lyndsey gives Ben the opportunity to go to Paris with her, he turns it down, because Seattle's rolling in and the Sox are 3 1/2 games behind New York and Ben says that they need him. Later, the Red Sox are in the ALCS against New York, and fall behind three games to none. Then, Ben decides to sell his Red Sox tickets to make Lyndsey happy and say that he loves her. She's at Game 4, and Lindsey has to find a way to get him to stop selling his tickets, and can the Sox finally win it all?—soxboy06
Ben Wrightman is a 7-year-old going to a Red Sox game with his Uncle Carl. His uncle treated him like a son because he had no kids of his own. The opening narrative explains that ever since that day, Ben became a die-hard Red Sox fan. Just about everything he owns bears the Red Sox name, emblem or the image of a Red Sox player (with the exception of his toilet paper, which bears the New York Yankees insignia). Ben inherited his uncle's season tickets when he died.
The story picks up 23 years later with Ben (Jimmy Fallon) as a schoolteacher who is still rather immature for his age. He meets Lindsey Meeks (Drew Barrymore), a professionally successful workaholic executive. When he first asks her out, she rejects him, but she later changes her mind and agrees to go out with him.
On their first date, Ben finds Lindsey very sick. She has food poisoning from a new restaurant where she had dined at earlier during the day. Lindsey runs to her bathroom and vomits. Ben decides to stay over for the night and nurse her back to health as well as clean up her bathroom. The next morning, Lindsey, feeling better, finds Ben sleeping on her couch. Ben wakes up and he and Lindsey end up developing a romantic relationship with each other.
Overcoming her initial hesitance, she becomes attracted to him because of his ability to show a passionate commitment to something. That spring, he later pretends he is proposing to her, but instead asks her to the Red Sox home opener, where Stephen King (a longtime Sox fan) throws the first pitch. Lindsey attends, but not being a baseball or Red Sox fan, she knows nothing about the Curse of the Bambino or even how to pronounce the name Yastrzemski. The two continue to attend the games together until one summer night when Lindsey attempts to catch up on work by taking her laptop to the game. Not paying attention to the game, she is knocked out by a line drive foul ball by then Baltimore Orioles shortstop Miguel Tejada off Mike Myers. She eventually recovers but stops going to the games.
Things take a turn for the worse when Lindsey invites Ben to go with her to Paris and he rejects the offer because the Red Sox are in the heat of the playoff race. Before leaving for Paris, she tells Ben she is "late" and may be pregnant with his child, though they later learn she is not. Lindsey starts to become fed up with Ben's obsession with the Red Sox. Ben agrees to miss a game against the Yankees in order to go with Lindsey to her friend's birthday party.
Ben and Lindsey have a wonderful time together, and after making love, he tells her it was one of the best nights of his life. Moments later, Ben receives a call from his ecstatic friend Troy who informs him that the Red Sox overcame a seven-run deficit in the bottom of the ninth inning to pull off one of the greatest comebacks in team history. Ben becomes irate that he missed such a historic Red Sox moment, greatly hurting Lindsey's feelings. After Lindsey miserably declares he has broken her heart, he and Lindsey separate for a while.
Ben soon misses Lindsey and visits her in a futile attempt to reconcile. He eventually feels her loss so deeply that he plans to sell his season tickets to Chris, Lindsey's girlfriend Robin's husband, in order to prove that she means more to him than the Red Sox do. Lindsey finds out about his plan during the celebration for her much-anticipated promotion.
Immediately leaving the celebration, she rushes to the ballpark to try to stop him. She gets in during the 8th inning of the Red Sox-Yankees playoff game when the Sox are just 3 outs away from being swept. Ben is actually in the process of signing a contract with Chris as they sit in the stands. Because she is unable to reach Ben from her section in Fenway Park in time to stop him from signing the contract, she illegally runs across the field, deftly avoiding security personnel as she eventually reaches him. She tears Chris' contract in pieces and explains that if he loves her enough to sell his seats, then she loves him enough not to allow him to do so. The two reunite and kiss in front of the entire crowd.
The film ends with a narrative explaining how the Red Sox won that game, then beat the Yankees three more times for the pennant, later sweeping the National League champion St. Louis Cardinals in four games for their first World Series title in 86 years. Ben and Lindsay get married. She gets pregnant but the film ends with a narrative explaining that the baby will be named after one of the players, Ted (for Ted Williams) if it's a boy and Carla (for Carl Yastrzemski) if it's a girl, with the narrator hoping for a boy.
