Story :The story of Vince, New England's most successful divorce attorney. To Vince, life is one big competition, and losing is unacceptable. This also applies in his dating life with his love 'em and leave 'em approach. Then Vince meets Jane, who is beautiful, successful and also extremely driven. Together they enter into a series of entertaining wagers with each other where the winner gets to decide the fate of the loser.
Cast
Geoff StultsVince
Mena SuvariJane
Jennifer FinniganStephanie
Josh HopkinsKenny
Eric RobertsMr. Campbell
Kenan ThompsonMitch
Josh CookeKendrick
Debra Jo RuppTracy
Joey FatoneDelivery Guy
Tom DeNucciReno
Jonathan SilvermanTom
Kristin ChenowethMrs. Kemp
Dana AshbrookGary
Madeline MerrittMrs. Havacamp
Danielle GuldinEllen
Bridget EverettStella
Jennifer JostynRegina
Nadia DajaniNancy
Nicole LewisMasseuse
Jackie MooreHot Chick
Tom PapaJerk
Maria Kanellis-BennettHot Mess
Donna Del BuenoJudge Rioux
Tom PaolinoOpposing Counsel
Patty RossStenographer
Joseph PolisenaBailiff
Michelle VerdiMichelle
Sera VerdiSera
Chris VerdiBobby
Mark MussinaUmpire
Nathan LesserLittle League Pitcher
Wayne Alan HawkinsGay Club Emcee
Tom LaughlinGay Man #1
Nick PrincipeGay Man #2
David GereGay Man #3
Seth RosenblitGay Man #4
Fred SullivanGay Man #5
John GorhamLeather Daddy
Gregg BelloMan with Glasses
Patrick BlankGay Clubgoer #1
Will SeveranceGay Clubgoer #2
Chad Verdi Jr.Gay Clubgoer #3
Julie EcklesLittle League Mom
Tanja Melendez LynchRestaurant Patron
Tracy Michael LynchRestaurant Patron
Alexander Jose PaguayRestaurant Patron
Matt BurnsRestaurant Patron
Joseph MacleodRestaurant Patron
Ashton PenneyClub Patron
Devyn PenneyClub Patron
Amanda FinneganClub Patron
Jordan GriffinOutlaw
Scott LeonardOutlaw
Mikey AntuonoOutlaw
Cam BissittOutlaw
Cayden DuprasOutlaw
Nichols SymmesOutlaw
Logan LemayOutlaw
Cory RittallOutlaw
Luis VargasOutlaw
Jake GauslandOutlaw
David IannuccilliiOutlaw
Ryan DilorenzoOutlaw
Jessica LussierOther Little League Team
Cailene DuprasOther Little League Team
Marc CatoneOther Little League Team
A.T. DipinaOther Little League Team
Dylan LemayOther Little League Team
Mason BissittOther Little League Team
Roger MaranoOther Little League Team
Phil 'Skippy' AdamsGay Club Bartender (Uncredited)
Saintura BadeauGuy in the Club (Uncredited)
Ryan BoudreauTed (Uncredited)
Van BrockmannGay Club Patron (Uncredited)
Rick C. CorbettBar Patron (Uncredited)
Julie Ann DawsonHot Club Girl (Uncredited)
Miranda EvansRestaurant Patron (Uncredited)
Sandra L. FogellPatron (Uncredited)
Jimmy FolcoBowler (Uncredited)
Gwen KosakParent at Baseball Game (Uncredited)
Julian LowenthalGay Club Patron (Uncredited)
Noel MoorePretty Girl in Club (Uncredited)
Michael D. Murphy Sr.Nightclub Patron (Uncredited)