Ask This Old House began in 2002 and was spun off from a section of This Old House Magazine of the same name. Readers of the magazine or viewers of the show submit questions about various home repair or improvement projects, which are answered by the experts. It has been nominated for 5 Emmy Awards. The regulars on the show are O'Connor, Tom Silva, Richard Trethewey and Roger Cook. (This Old House veteran Norm Abram does not appear on Ask This Old House due to numerous other commitments on Abram's part, notably his involvement in The New Yankee Workshop.) Guest experts appear to answer more specialized questions. The show takes place in "the loft" of a rural barn somewhere in the Boston area. Most of the questions are answered in the loft, but one or two homeowners in each episode receive a visit from one of the show's three tradesmen (or a guest tradesman if the project is not construction, plumbing/heating or landscaping related such as electrical or painting projects), who assist in either starting or completing the task with the homeowners' help. O'Connor sometimes assists in these projects. There is also a feature entitled "What Is It?" in which three of the four regulars try to guess what an unusual tool is used for. The adjudicating fourth regular reveals the actual use. Beginning with the 2007/08 season, this program added a "useful tip" segment provided by a viewer of the show. The useful tip segment is a revival of a short-lived feature of This Old House when Vila hosted the show.
The opening credits feature a GMC van towing the blue Ask This Old House trailer around Boston and rural Massachusetts before reaching its final destination, the barn. The short, twenty-five-second version shows Silva, the passenger, picking up four coffees from a drive-through, while the driver in the longer, forty-second version is shown to be O'Connor. In both versions, after pulling into the driveway beside the barn, the footage cuts to Richard Trethewey handing out the coffees to the other three regulars.
Prior to O'Connor's installation as host, the driver was Steve Thomas, the host for the show's first year.
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