Longtime best friends Sid and Jonesie are dumped by their respective girlfriends. Both without a living situation, they decide to become "bromates", bros who are roommates, which puts their relationship to the ultimate test.

A womanizing yet lovable loser, Charlie, a waiter in his early 30's who dreams of selling his book entitled "7 STEPS OF HEALING THE MALE BROKEN HEART" finds himself still working in restaurants to survive in the Big Apple. Low on cash, he's left with no other choice but to look for a roommate to share his tiny studio. Surprisingly, the first person to answer the ad is his ex and only love of his life Pam, who broke his heart and disappeared without reason and the inspiration behind his book. The Pam he remembered was a youthful spirit with lots of money who is now broke and disheveled. A new story begins and it is up to Charlie to find out why she ran out on him and what's happened to her over the past three years. With a potential new love in his life, he must gather the strength to help Pam get back on her feet without rekindling old feelings.

It is freshman year at Coolidge College and Van Wilder is ready to party. To his dismay, all the girls have taken a vow of chastity and the dean rules the school. Van embarks on a crusade to land the campus hottie, Kaitlin, and liberate his school from sexual oppression and party dysfunction.