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NOTE: This spoiler was submitted by Heidi.

The film starts with Garrett (Justin Long) hanging out with his girlfriend Amy at his apartment. He ordered takeout food for her birthday, and eventually he tries to get her to go to his bedroom. She stops him to ask for her birthday present, which confuses him as she had previously told him that she didn't want him to get her a present. She tells him that she wanted him to think she was a "cool girlfriend" by being so low maintenance, which would then inspire him to get her a really great gift. He's very confused by her games and she yells at him that he isn't as fully committed to their relationship as she is and breaks up with him.

Erin (Drew Barrymore) works at The New York Sentinel as a summer intern and her two fellow interns are much younger. She is feeling dejected as her supervisor harshly edits her writing. He's not a mean boss, simply not engaged with Erin nor is he very sympathetic. She tries to speak with him about getting a writing assignment that will actually get published, as most of her assignments thus far have been unpublished. He gives her an assignment to write about a Make-a-Wish type program, which she gladly accepts.

Garrett goes to a bar with his friends Dan (Charlie Day) and Box (Jason Sudeikis) who try to cheer him up over his breakup. He is disappointed but his friends point out that he consistently has the same problems in relationships - he doesn't fully commit to the relationship. Erin is at the same bar with a friend and plays a Centipede arcade game. Garrett lines up behind her and puts a quarter on the machine to indicate that he wants the next turn. Erin brushes him off and says he'll be waiting a long time because she won't be done anytime soon. He blocks her view of the machine and she yells at him because she was so close to breaking the high score, held by ERL. As Garrett watches her enter her initials for the second place, he realizes that she is ERL and lets her know how much he has admired ERL from afar and has tried to break the top score. He apologizes for ruining her game and offers to buy her a beer. Erin agrees and joins his table and they decide to enter the bar's trivia contest as a team. Much to the annoyance of the bartender, they keep shouting out the answers before everyone else has a chance to hear the answer choices. They're clearly having a good time with each other and head back to Garrett's place and end up sleeping together.

The following morning, Garrett wakes up to find Erin trying to put her clothes on very quietly and sneak out. He stops her from sneaking out and asks her to have breakfast together, so they go to a diner. He tells her that he had a lot of fun with her and wants her number so they can hang out again. She gives him her number but explains that she's only in New York for the summer and is returning to Stanford in six weeks. He agrees that he would like to keep it light and casual as he is just getting out of a relationship. We see them spend their next six weeks together, very happy and enjoying being together.

Garrett works at a record label and is unfulfilled by his job as his boss assigns him to work with bands such as 3Z, a Jonas Brothers knock-off. His boss doesn't take Garrett's suggestions seriously nor does he give him a chance with the bands he really cares about.

Erin tries to speak with her boss to demonstrate her interest in getting a full time position. He tells her to call back the next year, in January, and they can discuss it. He also lets her know that her article is going to be published.

On their last night together, they are both clearly unhappy that they will be separating. As Garrett drives Erin to the airport, they are both sullen and don't say much to each other. They have an unhappy goodbye in his car as he drops her off. After a few moments, Garrett runs after her into the airport. They both realize how much they care about each other and don't want their relationship to end and decide to do a long distance relationship.

They continue their relationship through web chatting, texts and phone calls. Garrett's friends and Erin's sister, Corinne (Christina Applegate) encourage them to set official boundaries on their relationship to determine what it really means. They decide that they are in an exclusive relationship and will not see other people.

Garrett flies out to San Francisco over Thanksgiving to surprise Erin by showing up at the restaurant where she works, flowers in hand. As soon as they return to Erin's place (she lives at her sister's house), they start to have sex immediately on the dining room table. Corinne walks in on them and they realize that Corinne's husband (Jim Gaffigan) was having a midnight snack while seated at the dining room table.

At Thanksgiving dinner, another couple who is unhappily married joins them and the husband as well as Corinne's husband berate Garrett for making them look bad. They say it is easy for Garrett to be romantic for a few days but if he were in a real relationship every single day, he'd see how difficult it was. He is clearly feeling uneasy about all this. Later, he and Erin go to see a band called The Boxer Rebellion and he laments that such a great band can't get a record deal and yet he has to work with joke bands. They are joined by Erin's coworkers from the restaurant where she is a waitress, including Damon who is a very handsome, charming man. Garrett clearly feels jealous, but Erin assures him that he has nothing to worry about. They tell each other they love each other and continue on happily.

January rolls around and Erin calls her former boss at the paper to ask about a full time position. He tells her that they have just laid off 100 workers and aren't in a position to hire anyone. She is greatly disappointed and calls Garrett to tell him what happened. They are both disappointed as they were counting on her getting a job that would take her back to New York so they can be together again. She is angry and upset and they agree to talk about a plan later. She goes out with Damon to get drunk and commiserate. It seems like she might hook up with him, but she doesn't and goes home alone. In the morning, she wakes up extremely hungover and realizes that she has missed several calls from Garrett. She calls him and he tells her that he was very worried about her and she explains that she was out drinking with Damon. This upsets him and she promises that nothing happened. Garrett tries calling record labels in San Francisco to find a job that would locate him closer to Erin but can't find anything. He commiserates with an attractive coworker, Brianna, who is also in a long distance relationship and she encourages him to have phone sex. They try to have phone sex but get repeatedly distracted and give up. The stress of their long distance relationship is clearly taking its toll on them.

One of Erin's professors asks her how the job search is going and she lets him know that she has contacted all the New York newspapers and no one is hiring. He tells her that he has recommended her for a position at a San Francisco paper, but she tells him that she has her heart set on going to New York. He tells her that she shouldn't turn down any job that's willing to have her. She interviews and they offer her the job.

Erin goes to New York to visit Garrett and to let him know about the job and she hadn't even told him that she interviewed. He is upset by this as he takes it as her turning down the possibility of them being together again. They decide to go out to a bar with friends and Garrett ignores Erin and gets drunk. His attractive coworker Brianna shows up and they have a drink together. Erin tries to talk to Garrett who blows her off so she says that she will sleep at a friend's place that night. When she returns to Garrett's place in the morning, she sees Brianna run into the bathroom without her shirt on and she flips out, assuming they slept together, but it turns out that Brianna slept with Dan, Garrett's roommate. Garrett drives Erin to the airport and they fight about the job offer as she wants to make the decision together but he says that the decision is hers.

After returning to San Francisco, they are clearly feeling distanced from each other until Garrett calls and tells her that he wants to visit and he wants them to make the decision together as it affects both of them. She agrees and is happy that he wants to move forward together. As soon as he arrives, she tells him that she is going to turn down the job and move to New York. They are both very happy that they will be together again. Corinne has a private talk with Garrett and asks him if he understands that Erin is giving up everything to be with him, and that the sacrifice better be worth it. Erin's basic plan is to work as a waitress to earn money while she looks for a job. Garrett realizes that she shouldn't give up a good job just for their relationship and convinces her to take the job. They break up and he returns to New York.

Six months later, Erin is doing well at her job. She receives a package and it is a gift from Garrett, congratulating her on her great work and two tickets to a Boxer Rebellion concert. She and Corinne go to the concert to be surprised by Garrett. He explains that he quit his job and moved to LA to become the band's manager. They talk about how much closer LA is to San Francisco, only an hour by flight and six hours by car. They kiss and get back together.

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Garrett (Justin Long) and Erin (Drew Barrymore) meet and initially hook up and start dating with the understanding that Erin will be moving back to San Francisco in six weeks. After having a great time together, they decide to continue their relationship long distance. They talk on the phone, web chat and text, but only see each other twice in about a year and it's very difficult, despite the fact that they love each other and have a great time together.. They realize that their relationship will not work out as she is unable to get a job in New York and he can't find one in San Francisco. After several months, Garrett surprises her at a concert by revealing that he has taken a job in LA, much closer to her in San Francisco and they get back together.

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