|Jeff and Shirley|
|Portrayed by Joel McHale and Yvette Nicole Brown|
|“||You're the only one that understands me||”|
As with the other members of the study group, Shirley has a mostly maternal relationship with Jeff. Although sometimes annoyed with her mother henning and sermonizing, Jeff respects her beliefs and appreciates that she cares so much for her friends. They have recently learned about a past history they shared together, and it turned out that when Shirley was 12-year-old, she publicly humiliated a 10-year-old Jeff by making him wet his pants during a game of foosball. They have since made peace with what happened and have become much closer. Jeff has even stated that Shirley is the only one who understands him and Shirley has been shown to be one of the best influences on Jeff during his time at Greendale. Jeff is portrayed by Joel McHale and Shirley is portrayed by Yvette Nicole Brown.
Jeff and Shirley bond over a mutual love of gossiping and trash talking. She later encourages Jeff that he may still have a chance with Britta since Britta told her about a sex dream she had about him ("Social Psychology"). She later tries to prevent him from fighting Mike Chilada ("Comparative Religion"). Shirley, along with Annie, pursues Jeff as the main suspect of what was believed to have been a sick April Fool's prank ("The Science of Illusion"). When Jeff and Britta get into an "A-Duh" off competition with some high schoolers, she and Pierce depants the annoying teens ("The Art of Discourse").
Shirley is at first pleased that Jeff and Britta are dating but is then disappointed when it's revealed that they were only competing against each other to see who would crack first. Jeff has to talk with Andre Bennett after it's discovered Shirley might be pregnant with Ben Chang's baby ("Asian Population Studies"). Shirley asks Jeff to get Chang to sign a form giving up any parental rights he has over what could be his and her's baby ("Custody Law and Eastern European Diplomacy"). Shirley questions Jeff's statement that he has "chemistry with everybody" and says that he might be intimidated by her sexually ("Paradigms of Human Memory").
It is revealed in the episode "Foosball and Nocturnal Vigilantism" that they share a past history. She once bullied him when they were kids and this later shaped the personalities they have today; Jeff buried his feelings and decided to adapt a more detached persona and Shirley realized she went too far and became religious. Jeff is asked by Shirley to deliver a toast in her upcoming re-marriage to Andre Bennett ("Urban Matrimony and the Sandwich Arts"). While high on anti-anxiety medication, Jeff has a narcissistic Hulk-like rampage and kisses Shirley ("Contemporary Impressionists"). Jeff asks Shirley to accompany him to a carnival being held on campus so he can check out an ex-boyfriend of Britta's and this is where Jeff reveals Shirley is the only one who understands him. During the summer, Shirley asks Jeff to represent her in "Greendale Court" in her case against Pierce over their partnership in a sandwich shop ("Introduction to Finality)".