During the campaign stop in Richmond Hill, Hudak broke the ice with little Fabian Lai by talking about the four-year-old's bright red sweater, which featured the "Sesame Street" character Elmo.
Hudak told the youngster about his own three-year-old daughter Miller, who will soon be four.
While shy at first, Fabian soon warmed up to Hudak and was all smiles as the Tory leader knelt down to fit him with tiny black and white skates.
Hudak reminisced about his own childhood, saying his father used to take him out to buy new skates as well. He then helped a rather wobbly Fabian stand tall in his new footwear.
At one point Hudak commented on Fabian's colourful "Thomas the Tank Engine" socks, prompting a reporter to say the Tory leader knew his characters.
Hudak drew a murmur of laughter when he then quipped, "I know a few characters in the (press) gallery too."