You can win your very own custom illustration (like this, or this) simply by exercising your wit and humor! In the comments below, enter dialog that should appear for the characters. Keep it suitable for prime time television, make it funny, and just win, baby!
As an example:
Rollerskater1: Yes, I am wearing a disco skating outfit and carrying a purse. Thanks for the directions and ...
Rollerskater2: ... here's your tip. Don't "blow" it all in one place, heh!
Shoe Shine Skater: Thanks!
Good luck everyone!