More than a dozen Angelenos navigate Valentine's Day from early morning until midnight. Three couples awake together, but each relationship will sputter; are any worth saving? A grade-school boy wants flowers for his first true love; two high school seniors plan first-time sex at noon; a TV sports reporter gets the assignment to find romance in LA; a star quarterback contemplates his future; two strangers meet on a plane; grandparents, together for years, face a crisis; and, an "I Hate Valentine's Day" dinner beckons the lonely and the lied to. Can Cupid finish his work by midnight?

In Manhattan, the lawyer Liv and the school teacher Emma have been best friends since their childhood. They both are proposed to by their boyfriends on the same day and they plan their wedding parties in Plaza Hotel, using the services of the famous Marion St. Claire. However, due to Marion's secretary's mistake, their weddings are scheduled for the same day. None of them agrees to change the date and they become enemies, trying to sabotage the wedding party of the rival.

For three years, Andrew Paxton has slaved as the assistant to Margaret Tate, hard-driving editor at a New York publisher. When Margaret, a Canadian, faces deportation for an expired visa, she hatches a scheme to marry Andrew - he agrees if she'll promise a promotion. A skeptical INS agent vows to test the couple about each other the next Monday. Andrew had plans to fly home that weekend for his grandma's 90th, so Margaret goes with him - to Sitka, Alaska - where mom, dad, and grams await. Family dynamics take over: tensions between dad and Andrew, an ex-girlfriend, Andrew's dislike of Margaret, and her past color the next few days, with the INS ready to charge Andrew with fraud.

Can two serial cheaters get a second chance at love? After a one-night stand in college, New Yorkers Lainey (Alison Brie) and Jake (Jason Sudeikis) meet by chance twelve years later and discover they each have the same problem: because of their monogamy-challenged ways, neither can maintain a relationship. Determined to stay friends despite their mutual attraction, they make a pact to keep it platonic, a deal that proves easier said than done.

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