- During her youth Cheerilee was a real outgoing wild card. Dancing to those 80's rock tunes and flirting with anypony that was interested. Since species diversity wasn't as common back then, she flirted with both mares and stallions. In other words, Cheerilee is bisexual.
- Cheerilee was the 'big sister' friend in that she would always be the one who'd introduce and settle others into the party/club scenes. This is how she got her cutie mark, although she twists the story for younger ears. Yes Cheerilee is a great teacher to younger ponies, it's just unclear of whom these younger ponies were.
- As she grew she mellowed over the years. She prefers the bar over the club as it's much more peaceful and has better drinks. She's claimed her spot in the bar as the pool champion. Oh how she loves to show off and beat all the hard stallions who underestimate her.
- Before the love potion, Cheerilee had an eye for Big Mac as he was one of the most eligible stallions in Ponyville. Even afterwards the pair decided to date but Big Mac decided to end it after a while. He tried to end it off on good terms and Cheerilee tried to agree, but she couldn't help feeling upset.
- One of the nights where she wallowed away in despair, she heard a commotion outside of the bar. Some stallions were picking on the recently heartbroken Marble Pie who wandered down after running off. After challenging and beating them in several games of pool, they left Marble Pie alone and Cheerilee decided to comfort her. It was totally because she felt bad and could relate. Not that she was cute or anything.
- When Marble revealed who broke her heart, Cheerilee was mixed in deciding if she should be angry that it was Big Mac or that Big Mac hurt this innocent sweetheart. But looking at Marble's crying face she decided that dealing with him will come later.
- So Cheerilee ends up with Marble Pie. The outgoing and confident teacher fell for the shy little rock farmer. Cheerilee loves coming home to her and treating her to romantic dates and show off her mad pool skills.
- Cheerilee does not deny that she has a flirty mind outside the PG classroom, but she will deny fantasizing about having her way with her girlfriend on her desk.
- Cheerilee avidly believes that Marble's kisses give her extra good luck at the pool table. Must be why she purposely loses the first rounds. Definitely not to make up an excuse to make out for extra extra luck.