"Well, I guess that's something to smile about!" - Smiley
| Smiley Sundae|
|Relatives||Husband: Phil Eggtree (RT2 Ending)|
|Favorite Thing||Education, smiling|
|Least Favorite Thing||Distractions|
Smiley Sundae is the only known female student of Riddle School, and she simply loves school. She is rarely seen without a smile on her face; the only times she is shown not smiling in the RS series are in Riddle School 2 and Riddle School 5 (and Riddle Transfer 1 and 2). Phil once teased Smiley by drawing a face of mustard on the cafeteria wall in the first game and was then sent to Mr. Kahm's class.
The most common misconception in the Riddle School series, according to the Riddle School 5 special features, is that Smiley is thought to be a boy. This was cleared up in Riddle Transfer when she used the hair spray on her head. Smiley is female, and she has been female since the first game.
Jonochrome (The creator of the series) has said that Smiley and Phil are not in a relationship. On November 20, 2011, a Newgrounds user asked JonBro if it was true that Smiley loves Phil, to which JonBro responded, "No, it's not.". However, in Riddle Transfer 2, they began to have relationships.
While her friends Phil, Phred, and Zack were undergoing great physical and emotional changes, Smiley—already basically smart and wise—simply learned you can find friends in the most unusual places. This might have been thrown out the window when Diz (the one in question) betrays them, and Quiz was even less likely.
In Riddle Transfer her last name was proved to be Sundae given the title "Eager Scholar" and grew hair after spraying hair spray on her head. She was given Sundae as a surname because her personality is happy and when JonBro thought of happy he thought of the sun. She was also given hair to finally let people know she was a girl. Once Riddle Transfer 2 came out, JonBro, who is now Jonochrome, says that once Phil got used to school, he thought that Phil and Smiley were perfect for each other. It was shown at the end of Riddle Transfer 2 that Phil and Smiley went on a date, got married, and lived a full life happy in the photo album. Also Smiley said that Phil Eggtree got better grades than her, much to his surprise.
- Smiley's design is heavily influenced by the pop culture smiley, the famous stylized representation of a humanoid smiling face.
- Smiley didn't have hair until Riddle Transfer.
- She wore a Red Sweatshirt in Riddle School 4 and Riddle School 5 (Phred's Dream).
- She mostly wears orange shirts.
- Interestingly enough, Smiley appeared in a green shirt in Riddle School, but is changed into a red sweatshirt in Riddle School 4, and an orange shirt in Riddle School 5.
- This could be explained by the fact that Diz mentioned the aliens changing the kids' clothes while they slept.
- Smiley is smart, but in the RT2 credits, it is proved that Smiley play games, too
- It is shown in RT2 that Phil has better grades.