Ask.com was originally known as Ask Jeeves, where "Jeeves" is the name of the "gentleman's personal gentleman", or valet, fetching answers to any question asked. The character was based on Jeeves, Bertie Wooster's fictional valet from the works of P. G. Wodehouse.

The original idea behind Ask Jeeves was to allow users to get answers to questions posed in everyday, natural language, as well as traditional keyword searching. The current Ask.com still supports this, with added support for math, dictionary, and conversion questions.

In 2005, the company announced plans to phase out Jeeves. On February 27, 2006, the character disappeared from Ask.com, and was stated to be "going in to retirement." The UK & Ireland edition of the website prominently brought the character back in 2009, however American visitors can go to the 'askjeeves.com' URL to see the new Jeeves as a 'skin', or background image.

InterActiveCorp owns a variety of sites including country-specific sites for UK, Germany, Italy, Japan, the Netherlands, and Spain along with Ask Kids, Teoma (now ExpertRank) and several others (see this page for a complete list). On June 5, 2007 Ask.com relaunched with a 3D look.

On May 16, 2006, Ask implemented a "Binoculars Site Preview" into its search results. On search results pages, the "Binoculars" let searchers capture a sneak peak of the page they could visit with a mouse-over activating screenshot pop-up.

In December 2007, Ask released the AskEraser feature, allowing users to opt-out from tracking of search queries and IP and cookie values. They also vowed to erase this data after 18 months if the AskEraser option is not set. HTTP cookies must be enabled for AskEraser to function.

On July 4, 2008 InterActiveCorp announced the acquisition of Lexico Publishing Group, which owns Dictionary.com, Thesaurus.com, and Reference.com.

On July 26th 2010, Ask.com released a closed-beta Q&A service. The service was released to the public on July 29th 2010.

The company uses different websites offering localized services for certain countries and its associated languages, including:

Ask Jeeves, Inc. stock traded on the NASDAQ stock exchange from July 1999 to July 2005, under the ticker symbol ASKJ. In July 2005, the ASKJ ticker was retired upon the acquisition by InterActiveCorp, valuing ASKJ at $1.85 billion.