Dylan Shenk is the son of Bill and Tina Shenk and the Bakers' neighbors in the first film. He is portrayed by Steven Anthony Lawrence.

He and his parents start out as the Bakers' new neighbors after they moved to Evanston and even played hockey with Jake and Mike in the house. His mom is very overprotective of him and isn't fond of him playing with the Bakers.

After he is landed in the hospital, after Tom accidentally crashed on him when the younger kids ruined his birthday party while they snuck out of the house being grounded, his mom, believing that they'll hurt her son, furiously tells Tom that he can no longer play with Tom's kids and Tom apologizes to Dylan for landing on him.

He makes his final appearance when Mark runs away and he and his dad agree to help find him, much to his mom's annoyance. He has since recovered from his injuries earlier in the film.