Predictive answers based on context modeling

A system and a method of displaying a predictive answer in a conversation window, are described. The method includes transmitting, to a device executing an application, a first message to cause the device to display a conversation window within the application, wherein the conversation window has a character entry field. The method includes generating, by one or more processors, a predictive answer based on a Uniform Resource Locator (URL) associated with the conversation window or a URL shape of the URL, wherein the predictive answer includes a predicted inquiry of a user. The method includes transmitting, to the device, a second message to cause the device to display the predictive answer in the conversation window.