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Marcy is an assistant to Senator John McGlory, who is having problems with a re-election campaign. Desperate for Irish votes, McGlory's chief of staff Nick sends Marcy to Ireland to trace McGlory's relatives or ancestors. Marcy arrives at the village of Ballinagra when it is preparing for an annual Matchmaking Festival. A well-dressed, handsome and single young lady, she becomes the center of attention for two professional matchmakers, Dermot and Millie, as well as for bartender Sean.

Natalie Becker is staying at home studying and working on an essay to meet the president while her father is away. Jeffrey Moran, a childhood friend (whom her father does not know) is having trouble with his stepfather, Jeremy, who is an immature bully, so she lets him stay with her. All sorts of trouble and misunderstandings ensue. Natalie's best friend Polly tries to date a pro baseball player, Zoo Knudson, and is very intrusive on Natalie's personal life, jumping to hasty conclusions. She is also ready to jump on a plane to New York to be with Zoo.

The high-school student Matt Leland lives with his twin brother and sister and his father in a house by the lake. When the teenager Casey Roberts moves to the house on the other side of the lake, Matt snoops into her room with his telescope. They meet each other and soon they fall in love with each other. One day, Matt is taking a test at school and Casey activates the fire alarm to stop the test. She is suspended and her father decides to check her into a psychiatric institution. However Matt breaks her out of the hospital. They travel in Matt's car and have lots of fun until the day Matt discovers that Casey has bipolar disorder with periods of depression and periods of elevated mood. When she tries to commit suicide, Matt realizes that she needs specialized help.

Jennifer does not fit in. A total misfit, she's as wacky as a teenager can be. Goth-ed out with multiple piercings, tattoos, and dyed hair, she listens to strange music, watches vintage TV, eats primarily chocolate, and self injures. But now high school is over and she needs a job. Can she possibly have anything in common with the overweight middle-aged man in the haberdashery window? He gives her a job, not to mention a real friendship.

On the last day before summer vacation, Michael Ryan finds an anonymous love letter in his locker. Michael has a crush on Deborah Anne Fimple, who is the most beautiful girl in high school, and his friend Roger Despard convinces him that Deborah has written the letter. Michael writes a love letter to Deborah and asks his best friend Toni Williams, who actually wrote the letter for him, to deliver the letter to Deborah that is also her friend. However, Toni reads the letter and rewrites it to Deborah, who immediately falls in love with the unknown author. Meanwhile, Michael's mother Connie Ryan finds Michael's letter and believes it belongs to her husband George Ryan and Deborah's father Lou Fimple finds Deborah's letter and believes it belongs to his wife Elizabeth Fimple. Michael dates Deborah while their parents are astonished with the betrayals of their mates. Michael soon finds that Deborah is a shallow teenager who only dates college students and he misses Toni. Furthermore, he realizes that she has written the love letters and he feels that he loves her. But Toni is aboard of a ship ready to travel to study abroad for one year. Will they meet each other?

Sisters Kat and Daisy work along with Jojo at the pizza parlour in Mystic, Connecticut. Kat, shortly off to Yale, finds herself drawn to a local architect she is babysitting for, while her more tearaway sister starts dating a guy from the money side of the tracks. Jojo leaves her man at the altar; she loves him but shies away from commitment. Meanwhile the fame of the pizza continues to spread; it seems to contain something almost ..... mystic.

Jonathan, a naive country boy, gets a scholarship to a classy prep school, where he rooms with suave, rich and handsome Skip. Skip decides it is his duty to see that Jonathan loses his virginity, so he sends Jonathan to Chicago, where Jonathan meets Ellen, a beautiful older woman, and they be- gin an affair which ends abruptly when Ellen discovers Jonathan is 17. During Christmas break, Jonathan visits Skip's house and discovers that Ellen is Skip's mother. Ellen tells Jonathan to leave when he rejects her advances, but then begins calling him and begging to see him. Finally, Jonathan agrees to meet her and plans to end the affair, but Ellen seduces him--and that's when Skip, who followed Jonathan, discovers them.

This light-hearted romantic comedy centers tells of love sought, found, lost, and found again, revolving around the lives of two college students in New York City. Sophomore Al Connelly meets the girl of his dreams, freshman Imogen, and true love abounds. The two engage on a whirlwind courtship--they pick a song, eat a cake together, even make love. But Imogen's fear of lost youth causes her to push away from Al, and they go their separate ways. Al attempts to rebound from the relationship, determined to forget Imogen, and he goes to desperate measures to do so. The story is told from the points of view of both Al and Imogen.

A man suspects his girlfriend of being unfaithful. So he sends her a letter, but then finds out that he was wrong. He has twenty-four hours to stop the package, prevent a disaster, and fall in love. The only problem is the delivery man will not stop until the package has been delivered.

A rich businessman, Dylan McDermott, mistakenly believes that Matthew Perry, who is bidding on a $90 million restoration contract, is gay and asks him to keep tabs on his mistress, Neve Campbell. Perry, who is not gay, falls for Neve in a big way but she thinks he's gay.

College poetry professor and poet Rebecca Trager Lott's husband Ben Lott has just died in a freak accident. Rebecca's support during this difficult time consists of her best friend Sylvie Morrow, her sister Lucy Trager, and her ex-stepmother Alberta Trager. Earth mother Sylvie is dealing with what she sees as the probable end of her own marriage to her husband Paul Morrow. Chain smoking Lucy is a directionless and insecure woman who is still mourning their mother's death fourteen years earlier from cancer. And Wall Street executive Alberta, who Lucy in particular doesn't like in her life (especially as Alberta and their father have since divorced) is a domineering but admittedly efficient woman who treats her personal life as an extension of her professional life. As time progresses and each woman deals with her own issues while trying to help Rebecca, a hunky house painter who they have nicknamed "Valentino" enters their collective lives. "Valentino" profoundly affects each of their lives, at the same time that Rebecca, the only one who is seen as having had the perfect marriage, provides what they hope is sage advice for their issues. What comes into question is the appropriate time that Rebecca is allowed to feel sorry for herself. She makes an admission about her marriage and about "Valentino" that may provide the answer.

Ronald Miller is tired of being a nerd, and makes a deal with one of the most popular girls in school to help him break into the "cool" clique. He offers her a thousand dollars to pretend to be his girlfriend for a month. It succeeds, but he soon learns that the price of popularity may be higher than he expected.

A young war reenactor makes a friend on the battlefield who helps him use strategy to take on his high school enemy. Driven by newfound confidence, he seduces the friend's fetching older sister and risks the friendship. Reality intervenes when the illness of his ex-addict father forces the anger his irony masks to the surface and he has to decide if staying in a fantasy world is worth the consequences.

Jake and Kristy Briggs are newlyweds. Being young, they are perhaps a bit unprepared for the full reality of marriage and all that it (and their parents) expect from them. Do they want babies? Their parents certainly want them to. Is married life all that there is? Things certainly aren't helped by Jake's friend Davis, who always seems to turn up just in time to put a spanner in the works.

In 1963 Brooklyn, Jeffrey Willis has just finished high school and isn't quite sure what the future holds. His parents expect him to go to college, but he is starting to find his close-knit family stifling. He gets a summer job at the Flamingo beach club where he meets Phil Brody, a successful car dealer who fills his head with ideas about how to make his fortune. Phil is everything Jeffrey would like to be: popular, rich, and the best gin rummy player the club has ever seen. Jeffrey's coming-of-age includes a romance with the very pretty Carla Samson, but the shine on Phil Brody's philosophy of life wears off when he uncovers a significant flaw in his character.

Christopher leaves to pursue a career in writing. Due to a computer mixup he shares a dorm room with Alex whom he presumes is a man. However, Alex is the beautiful Alexandra! When upon first meeting her she gets on his nerves by partying and being with different men while at school! She is very outgoing. Christopher tries to get another roommate but while trying to get switched, she helps him in different ways by improving his love life and writing ability. The both of them fall in love with each other, but Alex has a boyfriend Slash who comes back for her. After putting her name on the wall of a men's bathroom, she realizes she is better of with Chris.

Jesse is charming, romantic, and he knows how to pop the question; he just can't face marriage. So, when he and Hannah split up during the same week that a former fiancée dies, he decides to figure things out. He visits each woman about whom he's been serious to ask what went wrong. His teen flame, an independent woman who sometimes sleeps with him, and a group of lesbians give him advice, as does Anabeth, dead but lively in his dreams. One ex remains furious, but with the help of her inventive colleague, the level-headed insomniac Laura, Jesse even gets to talk to her. It's on to Anabeth's funeral, where he'll see Hannah, and maybe grasp what has been eluding him.

Alice, a ten-year-old girl, looks up to her 17-year-old, wild neighbor across the street. She leads a three-person cheering section as the teenager, named Sheryl, falls in love and has forbidden liaisons with a young man from the bowling alley. Eventually, Alice becomes instrumental, in spite of her parents' alarm, in helping the two lovers to resolve the difficulties of their relationship and run away together. In the process Alice herself becomes more mature.