We describe experiments towards building a conversational digital assistant that considers the preferred conversational style of the user. In particular, these experiments are designed to measure whether users prefer and trust an assistant whose conversational style matches their own. To this end we conducted a user study where subjects interacted with a digital assistant whose response either matched their conversational style, or did not. We found that people strongly prefer a digital assistant that mirrors their “chattiness” and that this preference can be reliably detected.