Van Wilder starts his freshman year at Coolidge College and embarks on an adventure to land the campus hottie and liberate his school from sexual oppression and party dysfunction.

When high school sweethearts John (Seeley) and Kathy (Irvin) find out Kathy is pregnant, they decide to get married and move to Cambridge so John can fulfill his scholarship to Harvard. But faced with the harsh reality of their situation, Kathy leaves John behind, compelling him to rent a room from Dorothy (Potts), a psychic who encourages him as he struggles to balance school and fatherhood.