Win a Date with Eddy is a scam that Eddy tried to pull in "May I have this Ed?". For the scam, he taped a sign-up sheet to the wall, offering himself up as a date. Edd tried to talk him out of it, citing that it's expected that a boy ask a girl and also mentioning that it was unlikely that he'd get any entries, but Eddy ignored him. Soon enough, a name was put on a sheet, but it turned out that Ed had signed up. Annoyed, Eddy abandoned the scam, reasoning instead that all the cool guys "go solo" before dragging his friends off to his house to prepare for the dance.
- This is one of two scams that Eddy has pulled with the main objective being romance. The other one was his Kiss the Hunk scam in the Valentine's Day special.