Described herein is an in-text advertising display that presents web advertisements contextually related to retrieved web content about text on a web page. The text of a web page is analyzed to determine whether terms or phrases are associated with particular contextual definitions called entities. Portions of text associated with an entity are emphasized to the user. Detection of a user trigger event initiates retrieval of additional web content about the emphasized text and the retrieved additional content is displayed in a display window, within a pop-up advertisement, or within a quickbar window. An adjacent seamless window displaying web advertisements related to the additional web content is also presented to the user.