While on a business trip in Los Angeles, Edward Lewis, a millionaire entrepreneur who makes a living buying and breaking up companies, picks up a prostitute, Vivian, while asking for directions; after, Edward hires Vivian to stay with him for the weekend to accompany him to a few social events, and the two get closer only to discover there are significant hurdles to overcome as they try to bridge the gap between their very different worlds.

More than a dozen Angelenos navigate Valentine's Day from early morning until midnight. Three couples awake together, but each relationship will sputter. 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. An 'I Hate Valentine's Day' dinner beckons the lonely and the lied to.