I was a little wrong in my assumptions.
It went really well, up until the kids actually had to skate. Basically Will and Benny both freaked out. Benny was able to make it to the wall, but Will refused to try and skate by flailing his arms around, kicking and screaming! While Ray was trying to get Will off of the roller rink, Will tripped him. Ray is pumping his skates under him as hard as he can, trying not to fall for literally 30 seconds. But alas, Will tripped him again and they both toppled over. It seems like everyone is staring at us saying, "Why are you here with all of those kids?"
When Ray got up, I knew I was toast.
And for the record Ray, you were totally right!