A system and method for selecting calendar events based on examining the content of a user's recent e-mail activity. According to an embodiment of the present invention, a scheduling manager assembles a keyword list, wherein the keyword list includes a collection of keywords with associated weights for each keyword among the collection of keywords. If the scheduling manager detects at least two conflicting calendar events scheduled within a calendar program, the scheduling manager searches the at least two conflicting calendar events for at least one keyword on the keyword list. The scheduling manager computes a keyword weight score for each of the at least two conflicting calendar events. If one calendar event among the at least two conflicting calendar events has a highest keyword weight score, the scheduling manager schedules the one calendar event within the calendar program.