Wedding Daze (aka The Pleasure of Your Company)

Eccentric parents (Edward Herrmann, Joanna Gleeson, Matt Malloy, and Margo Martindale), including an incarcerated father (Joe Pantoliano), dominate this 2006 dark, wacky, romantic comedy in which a still-grieving, unemployed guy (Jason Biggs), who lost his girlfriend (Audra Blaser) on the night he proposed one year earlier, impulsively proposes to a waitress (Isla Fisher) he just met.
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