As Just My Luck opens, we meet Ashley Albright (Lindsay Lohan), and never has a girl been more aptly named: Everything is all bright for Ashley, who seems to be blessed by good fortune. On a rainy day, she steps outside with no umbrella ... and the rain stops as soon as she goes to step out from under the awning. She strides to the curb to get the cab that arrived just as she needed it ... and finds a fiver stuck to her heel as she gets in. As we follow Ashley through her day, the film makes it apparent that as lucky as she is, it's in direct proportion to the trials and tribulations of Jake Hardin (Chris Pine). Jake is a sad-sack schlub; he gets splashed by cabs, tears his pants, falls over and so on: If Jake dropped a piece of toast, not only would it land butter-side-down guaranteed, it'd probably set off a long-forgotten landmine as it landed. The other thing that becomes apparent as Just My Luck opens is that we, unintentionally, pretty much hate Ashley.
And it's not difficult, either; Ashley's life is a breeze, and ours is not. Things come easily for Ashley, and they don't for us. And Ashley seems likeable enough -- sharing good fortune with her friends in a shallow, callow way -- but it's pretty apparent that Ashley is unlikable because she's untested; she has no real character because she's never had to develop any in the face of adversity. Ashley's latest success is throwing a charity masquerade on behalf of record mogul Damon Phillips (Faizon Love, channeling Damon Dash, Jay-Z, Russell Simmons and every other hip-hop titan); Jake's latest doomed-to-fail scheme is getting a demo for the band he manages into Phillips's hands, which involves sneaking into the party. Between Ashley's work and Jake's subterfuge, the two still find time to have a dance; they kiss; and suddenly, our two ships crossing in the night have traded karmic cargo: Jake is now lucky, and Ashley is not.