Valentine's Day is a theatrical film based around the holiday of the same name. Directed by Garry Marshall. The screenplay and the story were written by Katherine Fugate, Abby Kohn and Marc Silverstein.
It is the first film to be co-produced by New Line Cinema along with sister studio, Warner Bros. Pictures. All subsequent films released after Valentine's Day were co-branded as New Line/Warner Bros. releases.
The film follows a group of related characters and their struggles with love on Valentine's Day.
Florist Reed Bennett (Ashton Kutcher) wakes up and proposes to his girlfriend Morley Clarkson (Jessica Alba), who accepts. However, Reed’s closest friends, Alfonso Rodriguez (George Lopez) and Julia Fitzpatrick (Jennifer Garner), aren't surprised when Morley suddenly changes her mind and leaves Reed a few hours later.
On a flight to Los Angeles, Kate Hazeltine (Julia Roberts), a captain in the U.S. Army on a one-day leave, befriends Holden Wilson (Bradley Cooper). Kate is doing a long travel to get back home only for a short time, and Holden states that she must really be in love to do so. When the plane lands and Kate has to wait hours for the taxi, Holden offers his limousine to allow her to be there on time.
Julia, an elementary school teacher, has fallen in love with Dr. Harrison Copeland (Patrick Dempsey), but does not know that he is married to Pamela (Katherine LaNasa). Harrison tells her that he needs to go to San Francisco for a business trip: on his way, he stops by at Reed's flowershop and orders two flower bouquets - asking for discretion. Wanting to surprise him and despite Reed's warnings, Julia flies to San Francisco, convinced that Reed was wrong. Julia finds out that he is married and finds him at a local restaurant. Dressed as a waitress, Julia makes a scene at the restaurant, making Pamela suspicious.
One of Julia’s students, Edison (Bryce Robinson), orders flowers from Reed, to be sent to his teacher. Julia suggests to Edison to give the flowers to a girl named Rani in his class who has a crush on him after telling Edison the meaning of love.
Edison's babysitter Grace Smart (Emma Roberts) is planning to lose her virginity to her boyfriend Alex Franklin (Carter Jenkins). The planned encounter goes awry when Grace's mother discovers a naked Alex in Grace's room, rehearsing a song he wrote for Grace.
Edison’s grandparents, Edgar (Héctor Elizondo) and Estelle Paddington (Shirley MacLaine) are facing the troubles of a long marriage. Estelle admits to Edgar about an affair she had with one of his business partners long ago. Although she is deeply sorry, Edgar is very upset.
Grace’s high school friends, Willy Harrington (Taylor Lautner) and Felicia Miller (Taylor Swift), are experiencing the freshness of new love, and have agreed to wait to have sex.
Sean Jackson (Eric Dane), a closeted gay professional football player, is contemplating the end of his career with his publicist Kara Monahan (Jessica Biel) and his agent Paula Thomas (Queen Latifah). Kara is organizing her annual "I Hate Valentine's Day" party, but soon becomes interested in sports reporter Kelvin Moore (Jamie Foxx), who was ordered to do a Valentine's Day report by his boss Susan Moralez (Kathy Bates), and who shares Kara's hatred of the holiday. Paula has hired a new receptionist named Liz Curran (Anne Hathaway), who dates mail-room clerk Jason Morris (Topher Grace). Jason is shocked when Liz turns out to be moonlighting as a phone sex operator. Liz explains that she is only doing this because she has a $100,000 student loan to pay off. Jason is upset, but eventually reconciles with her after seeing Edgar forgive Estelle.
Sean finally comes out on national television, and Holden, Sean's lover, goes back to him. Kate arrives home late at night to greet not her supposed boyfriend but her son (Edison). Willy drops Felicia off at home after a date and they kiss. Kelvin and Kara hang out at Kelvin's news station where they later kiss. Alfonso dines with his wife, and Grace and Alex agree to wait to have sex. Edgar and Estelle reconcile and redo their marriage vows, Harrison eats pizza alone after Pamela leaves him, and Morley tries to call Reed, who is instead starting a new relationship with Julia.
- Jessica Alba as Morley
- Kathy Bates as Susan Moralez
- Jessica Biel as Kara Monahan
- Bradley Cooper as Holden Wilson
- Eric Dane as Sean Jackson
- Patrick Dempsey as Dr. Harrison Copeland
- Héctor Elizondo as Edgar Paddington
- Jamie Foxx as Kelvin Moore
- Jennifer Garner as Julia Fitzpatrick
- Topher Grace as Jason Morris
- Anne Hathaway as Elizabeth "Liz" Curran
- Carter Jenkins as Alexander "Alex" Franklin
- Ashton Kutcher as Reed Bennett
- Queen Latifah as Paula Thomas
- Taylor Lautner as William "Willy" Harrington
- George Lopez as Alphonso Rodriguez
- Shirley MacLaine as Estelle Paddington
- Emma Roberts as Grace Smart
- Julia Roberts as Cpt. Katherine "Kate" Hazeltine
- Bryce Robinson as Edison Hazeltine
- Taylor Swift as Felicia Miller
- Jonathan Morgan Heit as Tough Franklin
- Beth Kennedy as Ms. Claudia Smart
- Paul Williams as Romeo Midnight
- Christine Lakin as Heather
- Katherine LaNasa as Pamela Copeland
- Joe Mantegna as Angry Driver
- Brooklynn Proulx as Madison Copeland
- Nigel Quashie as Personal Trainer
- Kristen Schaal as Ms. Gilroy