AskMen was founded in August 1999, created by Ricardo Poupada, Christopher Bellerose Rovny and Luís Rodrigues, all three graduates of Concordia University's John Molson School of Business in Montreal. The company secured $500,000 in venture capital in 2000 while its main competitor, TheMan.com, obtained $17 million in financing from Highland Capital. In November 2000, TheMan.com shut down operations, providing an opportunity for AskMen to become the largest men's lifestyle website online. By 2001, AskMen surpassed the other websites in its category to become the largest men's lifestyle website. In 2005, AskMen was acquired by IGN.
In 2010 the site ranked #819 for world-wide traffic on Alexa. In December 2009, the site had an estimated 12 million unique visitors.
According to Hitwise, AskMen was ranked No. 1 (as of June 11, 2005) in the "Lifestyle – Men’s Sites" category, as it has over 40,000 articles available for free online.
AskMen launched a three-book series published by HarperCollins in May 2007, starting with their first book titled From the Bar to the Bedroom.