In Girl Meets Semi-Formal he asks Riley to their school's semi-formal after having waited ten months to muster enough courage to ask her after believing Lucas would would ask her. When Lucas did not ask Riley, he asks her to the semi-formal in the way she dreamed Lucas would ask her and she unintentionally agrees to go with Charlie instead of Lucas, causing Lucas to get jealous.
In Girl Meets Texas (Part 3), he and Riley went on a date, although Riley just agreed to it because she was heartbroken after seeing Maya with Lucas.
In Girl Meets the New Year, Charlie asks Riley to be with him at midnight however Riley lets him down gently saying the he deserves more. He then understands and sits on a bench with Auggie and counts down to midnight.
Riarlie (Ri/ley and Ch/arlie)
Charley (Char/lie & Ri/ley)
Chiley (Ch/arlie & R/iley)
Rarlie (R/iley & Ch/arlie)
Rilie (Ri/ley & Char/lie)
Rirlie (Ri/arlie & Cha/rlie)
Notes: Please add your name to the list in alphabetical order if you are a Charlie and Riley shipper!