Main Details A Lot Like Love Cast: Ashton Kutcher - Oliver Geary Amanda Peet - Emily Friehl Kathryn Hahn - Michelle Kal Penn - Jeeter Ali Larter - Gina Gabriel Mann - Peter Taryn Manning - Ellen Geary Jeremy Sisto - Ben Tyrone Giordano - Grahm Geary Director: Nigel Cole Genre: Romance Runtime: ??? Minutes 2005 Herschel Bleefeld - Bill Moon Bloodgood - Bridgette Ron Bottitta - Venture Capitalist Lionel D. Carson - Venture capitalist Brendan Patrick Connor - Wedding Guest William Stanford Davis - Priest Steve Filice - Caterer 3 Aimee Garcia - Nicole Uziyahu Bryant Gonzales - Praying Traveler (Hasidic Jew) Steven Guy - Venture Capitalist Christine Holz-Lusita - Catty Actress Daniel A. Jacobs - Warehouse Supervisor Kevin R. Kelly - Park Ranger Jeff Lam - Annoyed Chinese Waiter Ralph Lister Lindsay MacFarland - Woman at Gallery Ryan Miller - Booger Boy Brad Newman - Dinner Guest Lindsay Roth - Female Wedding Guest Joeanna Sayler - Gallery Owner Jocelyn Seagrave Kevin Skinner - Guy at party Sean Smith - Lawyer Sean Smith - Lawyer Anastacia Spiegel - Dinner Guest Melissa Van der Schyff - Carol Maggie Wagner Julie Wittner - Casting Assistant