Synopsis
When JESSIE ENGLISH (Grace) is dumped by her boyfriend PERRY mid-skydive, she decides to drop him -- literally, into a lake -- and accidentally crashes into a wedding, ruining the bride’s dress. A video ends up online, much to her dismay. Jessie, a flower shop owner turned viral sensation, meets LIZ RAFFERTY with her fiancé and mayoral candidate, ROBERT BARTON. Liz asks Jessie to plan her wedding, which is in a little over a week. Robert recognizes her from the skydiving wedding video, hires her anyway, and reveals that a man she ran into outside is their caterer, LAWRENCE PHILLIPS (Irons). Jessie is also introduced to Robert’s no-nonsense campaign manager, BEV, and his brother JIMMY BARTON.
As everyone prepares for the 'perfect' wedding for Liz and Robert, it becomes clear that their own relationships are far from perfect. Jimmy is a reality dating show contestant, where he’s handcuffed to a woman named SVETLANA, for a chance to win two million dollars. Lawrence is set up on a blind date, with a beautiful woman named SARA (Keaton), who happens to be actually blind. She crashes into a table, knocking over a display.
Meanwhile, CAPTAIN RITCHIE welcomes a group of tourists to his duck boat tour and meets a beautiful girl with a glass slipper tattoo on the back of her neck. He tries to get her name after the tour but misses her, heartbroken. He is approached by a reporter, GAIL LOVEJOY, who invites him to be the subject of a news segment to find his lost Cinderella.
As these outrageous personalities come together in the name of romance, it becomes clear there is no such thing as perfect timing when it comes to love.