Shirley Bennett had a strained relationship with Pierce Hawthorne from the moment they both joined the study group. His initial attraction to her followed by his elitist attitude and boorish behavior was a constant source of irritation to her. Throughout their time at school, Shirley did her best to put up with his racist and bigoted comments understanding that it was based mostly on ignorance and not hate. In spite of the rocky start to their relationship the two eventually became business partners and were co-owners of a sandwich shop on campus. When Pierce died, Shirley mourned his passing along with the rest of their study group. At a reading of his will, Pierce left a message for Shirley telling her how much respect he always had for her. Their first appearance together was in the Season One "Pilot". They are portrayed by Yvette Nicole Brown and Chevy Chase.
Pierce and Shirley were both invited to attend a Spanish study group meeting by Abed Nadir. Earlier in class Pierce had made unwanted advances on Shirley and continued to go so at the study session. Pierce seemed completely unaware of his actions despite Troy Barnes and Shirley herself pointing this out to him. Although Pierce's crush on Shirley eventually subsided, their relationship remained strained due to his insensitive behavior. It reached a boiling point when Pierce went too far with a joke and greatly embarrassed Shirley in front of the Study group. A clueless Pierce was unaware of how upset Shirley was and was angry at her for running his joke. Feeling this time he crossed a line she couldn't forgive, Shirley had Pierce kicked out of the study group. However, she soon left the group when they tried to trick her into letting Pierce come back. Ultimately, Pierce and Shirley ended up reaching an accord after finding some common ground in how they were mistreated by their friends. With this new truce in effect they helped Jeff and Britta defeat some high schoolers in an impromptu taunting competition.
"Pilot": Pierce and Shirley are invited to a Spanish study group meeting by Abed.
"Debate 109": Shirley and Pierce attend the Debate competition to support Jeff and Annie.
"Comparative Religion": At her Christmas party, Shirley performed a few songs while Pierce accompanied her on the keyboard.