Men Seeking Women (1997)

Three best friends mess up their already flagging love lives with an illfated bet They each put two thousand dollars in a bank account with the winner being the one who can not only get a girlfriend but also live with her for three months Nick decides to hoodwink his two friends by faking a relationship with an old girlfriend from college while Al proceeds to embark on a series of the worst dates imaginable and Les finds himself getting deeply involved with an alluring but mysterious woman who may or may not be married to a mobster Hilarious antics lead to an unexpected outcome guaranteed to surprise