Will Tomlander can be a prankster when the occasion calls for it. His favourite is the classic shaving cream in hockey pants or skates, as it is an easy one to do and also one that does not really harm anything or anyone. Of course he will not do it before a game, just during unimportant practices. Although, this one time he pranked the coach by saran wrapping the inside of the door so that when the coach tried to walk into the door in the morning he walked right into the saran wrap and kind of got stuck in place. The coach still doesn't know who did the prank, really, and that is good because otherwise Will Tomlander will get into a lot of trouble and might have to do something bad like bag skates or barf runs.

On the ice, his favourite prank is to yell out "Look out behind you!" at other players or to try and call out opponents' nicknames in order to try to steal the puck.