Both D'Alessandro and Bruce Waddell trained as singles skaters at the Toronto Cricket, Skating and Curling Club, and initially tried out as a dance team at the suggestion of the TCC's dance coach, Andrew Hallam. D'Alessandro/Waddell were pre-novice champions at the 2016 Skate Canada Challenge, and then won the novice title at the 2017 Canadian Championships. Making their international debut as a dance team, they placed fourth at the 2017 Bavarian Open in the advanced novice division.