When best friends Max, Drew, Jellyroll and J-Ron graduated from high school, they made a bet to see which one bring the sweetest, most beautiful woman to their ten-year reunion. Ten years and some creative investing later, their $50 bet is now worth $50,000! As the reunion draws near, each guy has his eyes on the fresh kitty. The only problem is, none of them can find a date! What to do Go online, check out some chat room, and find the woman who's gonna deliver the prize! After lining up a series of hilarious dates to narrow the field, the guys each think they've found their dream date, and set out to collect their 50k. The reunion, though, doesn't go as planned, and the guys quickly find they've been duped by their women, and that they really shouldn't believe everything they're told - or see - inside an internet chat room!