Dena's Cass went, with some skates she'd acquired .... somewhere. Because ew, rental. She's damn good on skates. She'd have been challenging people to races and hung out with whoever. She PROBABLY won't pickpocket anyone she knows, but anyone else who seems like a jackass is up for grabs.
Will went if any of the Losers or El wanted to, or if anyone else asked him to, and he would have hung out with Courtney a bit since they've chatted and are making friends. He's not great on skates, but he doesn't fall.