While attending college in New York City, sophomore Al / Alfred Connelly (Freddie Prinze Jr.) and freshman Imogen (Julia Stiles) begin dating. Al's roommate Monk (Zak Orth), who has become a pornographic film actor and director, tells him that love is illusory and fleeting. Monk gets paid $2500 per movie and is doing well for himself. Eddie (Shawn Hatosy) is Al's other roommate. Eddie wants to be part of the business, but Monk challenges Eddie to get a girl in bed by that night in their room, and he would be watching from Al's bunk. If Eddie succeeds, Monk agrees to get him an audition. Eddie and Monk go their separate ways, leaving Al looking for someone to spend some time with. Al and Imogen meet at the bar. Imogen was by the Juke Box picking songs when Al stops by and introduces himself. He says that he like female singers as his own mother was a DJ all her life and he has her influence in him. Lana (Rosario Dawson) is Imogen's friend. The girl that Eddie leaves the bar with is Lana. The night between Eddie and Lana goes weird as Al later finds out that Lana shoved her finger up Eddie's behind, throwing him off his game, and leading him to believe that he might be gay. Al and Imogen end up dancing together, though Imogen is approached by a fellow student Jim, who also offers her a drink. At the end of the night Imogen hugs Al, even though she wanted not to be in a relationship during her freshman year. Imogen says that she was in relationships all through high school and was looking forward to having a good time without being tied down. Al is intoxicated by the smell of her hair. Monk's co-star Cyrus (Selma Blair) shows up at the bar after Monk and Eddie had left and she flirts with Al. Cyrus is an MIT dropout and is now taking a break to explore herself and is looking to share herself. Monk is the closest person Al has for advice on the topics related to love. Soon, Al is visiting Imogen at her campus. Imogen hugs Al again and throws out all her rules about not dating anyone in her freshman year. Al finds that Imogen is majoring in art and has painted portraits of herself on album covers and so on. They do a fake therapy session to discover their likes and dislikes and also learn about each other's dating histories. Al takes Imogen to meet his parents Ray and Judy (Lucie Arnaz). They love spending time with each other. After three months they have fallen in love, and it is a first love for both of them. Imogen, an aspiring artist, arranges a private showing at an art gallery for Al's birthday, after which the two have sex for the first time. This was the honeymoon period of their relationship. Al loses a bet and must perform as an extra in one of Monk's films. This causes an argument between him and Imogen, who wants to spend time with him before she goes to France (in 2 weeks) for the summer. He abandons the film in favor of spending the night with her. Things are perfect and Al believes that they will remain this way. While in France, Imogen is asked by her cousin if she and Al will marry. This unnerves her as she is only nineteen, and she acts differently toward Al on her return. Al's father Chef Ray (Henry Winkler), who hosts a cooking show, wants to do a father-and-son show after Al graduates. His vision is of a reality TV show where Al and Ray travel all over the country in their large truck, and offer to cook dinner for families they pick on the fly with ingredients at the back of their truck. While they cook the food, they also teach their audience on how to cook various cuisines of food. Every week a new cuisine and a new home. But Al would rather pursue his dream of becoming a chef of French cuisine. Concerned that he and Imogen are drifting apart, Al arranges a picnic in the countryside. On the way back, she drives drunk and crashes into a tree. Seeing the accident as a sign, they try to improve their relationship. Though they seem happy, Monk predicts it is a precursor to a breakup. When Imogen declines to have sex one night, Al feels emasculated and has a sexual fantasy about Cyrus. Imogen fears that she may be pregnant, and though she turns out not to be, these further strains their relationship. At one of Monk's parties, Cyrus tries to seduce Al, but he declines. Meanwhile, Imogen spends time with musician acquaintance Jim (Ashton Kutcher). When Al learns she has agreed to design Jim's album cover, they argue and she leaves upset. The next day, she confesses she had sex with Jim afterward. After a tearful breakup, she moves to San Francisco to finish school. Al graduates but becomes depressed. Monk is too preoccupied with his new work as an author and lecturer to comfort him, and their friendship dissolves. After a period of isolation, Al starts dating again and has a casual relationship with Cyrus, but she eventually moves away. He enrolls in the French Culinary Institute but feels unmotivated and drops out and is reduced to bar-hopping with his single friend Eddie (Shawn Hatosy). Drunk and missing Imogen, he tries to purge himself of his feelings for her by drinking a bottle of her shampoo, resulting in his hospitalization. Al's parents throw a party with his friends to lift his spirits. Monk apologizes to Al, and they mend their friendship. Imogen appears, and they spend time catching up. She has become a cover artist for a San Francisco-based book publisher. She confesses that she misses him and gives him a book titled Down to You with her cover artwork depicting the two of them in love. They rekindle their romance, deciding that they met too young but can start over. Al takes a job at a four-star restaurant in San Francisco and surprises Imogen with a romantic evening.
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