Shirley Bennett (née Edwards) began the series as a recently-divorced woman who is taking courses at Greendale Community College to learn how to make a business out of her baking skills. Before enrolling at Greendale, Shirley was a married stay at home mom with her two sons, Jordan and Elijah. However, her husband Andre left her and the family for a stripper. It's implied that in this dark time in her life she started drinking heavily. Despite her hardships, she claims that her husband leaving was the best thing that happened to her and that attending Greendale was her first step in improving her life. She has since made up with and remarried Andre, had another child with him and opened a sandwich shop in the Greendale Cafeteria. She is portrayed by actress Yvette Nicole Brown.
Shirley is a devout Baptist and is the most religious member of the study group whose surface good-natured personality belies some thinly-veiled rage issues ("Pilot"). While she is proud to be an African American woman and a mother she tries not to be defined by just those characteristics. Her age is something she is very sensitive about as she is one of the older study group members and often tries to prove to them that she is still relevant ("The Science of Illusion"). She becomes the "mother hen" of the group often offering unwanted advice or opinions to the other members ("Comparative Religion"). She admits to having a gossiping problem, one which has cost her past relationships by needlessly stirring the pot between her friends ("Social Psychology"). It's been suggested by the study group that she also has a baking problem and tries too hard to be liked by baking goods for everyone ("Remedial Chaos Theory"). She often struggles with tolerance for the other faiths of the non-Christian members of the study group ("Comparative Religion"). She has gone as far as trying to covertly baptize Annie (who is Jewish) at a pool party and suggested they baptize Abed (who is Muslim) while he was in a catatonic state ("Biology 101").
Shirley is invited to a Spanish study group by Abed along with a few other classmates. Although she discovers it's fake, she and the rest of the members decide to form a real one. She spends the year struggling to accept the fact her marriage is over and trying to build a new life while balancing the responsibilities left over from her old one. She eventually manages to juggle both her academic life and personal life all while trying to fit in with her new friends in the study group. She becomes close to Britta but comes into conflict with Pierce on a few occasions. The end of the year sees her supporting Britta bid for Tranny Queen and trying to offer the younger woman some advice on her relationship with Jeff.
"Pilot": Shirley gets invited to a Spanish study group by Abed.
"Spanish 101': Shirley and Annie, at Britta's suggestion, decide to hold a protest against Gautamala in honor of journalist who was killed by the government there.
"The Politics of Human Sexuality": Shirley and Britta help Annie break into the Deans office so she can get a good look at a anatomically correct statue she is supposed to put a condom on as part of a presentation at the STD Fair.
In Shirley's second year at Greendale she and the study group take Anthropology together. A crazy Halloween party at the beginning of the semester sees Shirley and Ben Chang having a one night stand although due to outside influences they have no memory of the incident. Shirley reconciles with her ex-husband Andre Bennett and they start dating. Her past history as an alcoholic is revealed when the study group celebrates Troy's birthday at a bar she used to frequent. She discovers she is pregnant and that due to evidence Troy presents to her, Ben Chang may be the father and not Andre. At the end of the year she gives birth in the Anthropology classroom and the baby's true parentage is revealed. She later takes a vote along with the rest of the study group on whether or not Pierce should be asked to rejoin them in the next semester. In the western themed end of the year school picnic, Shirley participates in what was to be a quick paintball game which turned into an all out war against Greendale's rival school City College. She successfully triggers a trap inside the school's library which eliminates a lot of the invaders. Later, she and Britta using the Campus security patrol cart launch a last ditch assault on the City College machine gun post and succeed in taking out but are unfortunately also eliminated themselves form the game.
"Anthropology 101": Shirley is happy that Jeff and Britta seem to be dating now and reveals to the study group how the couple hooked up during the paintball competition the previous year.
"The Psychology of Letting Go": Shirley is clearly upset that Annie and Britta are working on a project together and didn't include her in it .
"Messianic Myths and Ancient Peoples": Shirley's attempt to get Abed interested in working on a religious youtube video for her church inspires him to make the ultimate meta film.
"Epidemiology": The students at the school Halloween party become infected and crazed chasing Ben Chang and Shirley into the library restroom. The two share a moment and have sex but a government cover up erases their memories of the incident.
"Aerodynamics of Gender": Shirley, Britta, Annie and Abed take a Women's studies course and run afoul of Meghan and her mean girl clique. Thanks to Abed the Mean Girls are overthrown and the quartet takes their place as the new clique to be feared.
"Intermediate Documentary Filmmaking": Pierce plays mind games with the study group pretending to be on his death bed and bequeathing them things to mess with them. He gives Shirley what he claims is a candid recording of the study group mocking her.
"For A Few Paintballs More": A City College VS Greendale College paintball war errupts and Shirley joins Troy's commando unit to spring a trap for the invaders. Later, with the help of Britta and the Campus security patrol cart, Shirley makes a last ditch assault on City Colleges paintball machine gun nest.
In Shirley's third year at Greendale, she and the study group are taking Biology class together. She discovers a shared history she has with Jeff which had a profound impact on both of them. She later helps Abed out by participating in a celebrity impersonator Bar Mitzvah in order to cancel out his debt to Vinnie. Andre proposes to her and they get remmarried in an imptomptu ceremony while at the same time she becomes partners with Pierce in a proposed sandwich shop thanks to the encouragement of Britta. Towards the end of the year, she and the study group are expelled form school thanks to Ben Chang's machinations. Once she is reinstated, she and Pierce are given the go ahead by Dean Pelton to open up "Shirley's Sandwiches" in the school cafeteria. However, Pierce takes her to "Greendale Summer Court" in order to be named sole owner of the shop. Jeff represents her against his old colleage Alan Conner who is representing Pierce. Jeff delivers a patented "Winger speech" that settles the dispute.
"Competitive Ecology": When the study group tries to pair off for Biology lab partners, Shirley discovers she's the member of the study group that no one one to be partners with when Abed uses it popularity to determine who should be paired off together.
"First Chang Dynasty": As part of the plan to rescue Dean Pelton and take down Chang's regime at school, Shirley infiltrates Chang's brithday party dressed as a male baker who delivers his birthday cake.
"Introduction to Finality": Shirley and Pierce have a dispute over their new sandwich shop and Jeff ends up having to represent her in "Greendale Summer Court" when Pierce decides to sue her for sole ownership.
In Shirley's fourth year at Greendale, she is now running the Sandwich shop while finishing up her business studies at the school. She and the study group are taking History 101 after a registration snafu forces them to abandon their plans on taking another class called "History of Ice Cream". She invites the study goup to attend her Thanksgiving Day dinner with her in-laws. After Ben Chang returns to the campus claiming to have amnesia, she hires him as a worker at Shirley's Sandwiches.
"Biology 101": Shirley takes part in "Senoritis" pranks with Annie.
In their freshmen year together, the two bond while gossiping over Britta's then-relationship with Vaughn ("Social Psychology"). In the spirit of the holiday season, she also tries to persuade Jeff not to fight Mike the campus bully ("Comparative Religion"). In their third year at school together, they learn about a shared history together ("Foosball and Nocturnal Vigilantism"). When Shirley was twelve years old she bullied a ten-year-old Jeff during a foosball game. This incident had a profound effect on both of them as Shirley realized she went too far, gave up bullying and became a more caring person. They have made peace with each other over the past and have since developed a close relationship ("Origins of Vampire Mythology").
As the more compassionate members of the study group, they often take issue with many of the morally ambiguous antics of their friends. Because she is the youngest of the group, Shirley is often overprotective of her which sometimes annoys Annie (along with Shirley's various attempts to convert her to Christianity). Shirley for her part is sometimes annoyed when Annie unintentionally reminds her of their age difference as she is one of the older mebers of the study group. In spite of this, they have developed a good friendship and will often find the same things adorable. This leads to them both saying "Aww!" at the same time which has become a running gag on the show. They also have a secret handshake first shown in "Communication Studies".
Like the other study group members, Shirley treats Abed in a motherly way. She is often unsure of what to make of Abed, and is often annoyed by his childish antics. She also questions the true nature of his relationship to Troy which has become a running gag on the show. Although impressed with Abed's powers of observation and skill as a filmmaker she is shown to be wary of it, especially when he goes too far with his abilities. In their second year together at Greendale, Abed was inspired by Shirley to shoot a religious film but took his meta concept too far and made an overproduced mess. Shirley helped him salvage his reputation by destroying his film and in the process the two came to a better understanding of each other.
Britta and Shirley get along very well despite some major differences of opinions. Britta's Athiestic beliefs sometimes annoys Shirley who is devout in her Christian faith. Even so, Britta was protective of her friend when she reunited with her ex-husband not wanting her to be hurt again and put aside her own discomfort with marriage to help Shirley plan her wedding to Andre. Shirley for her part was supportive of Britta when dealing with her romantic issues with Jeff and also taught her the importance of women bonding in the restroom. Their close friendship was demonstrated when they both gravitated towards each other when given a choice of who to be lab partners with in Biology.
Shirley has a strained relationship with Pierce. She tries her best to put up with his racist and bigoted comments as she realizes it's not done out of hate but due to his own ignorance. In their first year together at Greendale he made unwanted advances towards her ("Pilot") and also depantsed her ("The Art of Discourse"). Pierce's villainous actions in their second year ("Intermediate Documentary Filmmaking") at school led to Shirley and the rest of the study group, sans Annie, to vote him out ("A Fistful of Paintballs"). After meditating all summer at a religious retreat, Pierce returned with a friendlier attitude, and Shirley welcomed him back to the study group. Later in their third year, Pierce and Shirley form a business partnership and open a Sandwich shop at Greendale ("Introduction to Finality").
Shirley mother hens Troy as much as she does the rest of the study group and is often put off by how close he is with Abed. It is later hinted that the two could see themselves as sexual options ("Romantic Expressionism"). Troy once proposed a secret alliance between the two of them to win the 2010 Paintball Assassin game before being eliminated ("Modern Warfare"). In their Sophomore year together at Greendale, Troy learned through a voice mail Chang sent him that he and Shirley might have hooked up during the Halloween no one could remember and kept it to himself until he could verify it ("Epidemiology"). When battle lines were drawn between Troy and Abed in their Pillow and Blanket war, Shirley joined Troy's and told her husband Andre it was so that "Britta doesn't put him on the weed." ("Pillows and Blankets").
Shirley spent the entire first year at Greendale single often referencing her ex-husband in a negative light. In her Sophomore year, Shirley reconciled with and started dating her Andre. She learned she was pregnant but the baby's parentage was in question when it's learned that she had slept with Chang around the same time she reunited with her husband. Nevertheless, Andre made it clear to her that no matter who the father was he would not abandon her again and would be the father to the child. It was later confirmed that he was indeed the father. In Shirley's third year at school, Andre proposed to her again and she accepted. They were remarried in a quick ceremony in Group Study Room F.
Elijah, Jordan, and Ben are the children of Shirley and Andre Bennett. Although they are rambunctious and seem uncaring, both Elijah and Jordan have demonstrated that they have Shirley's kindness and compassion. Ellijah is named after the prophet and Jordan is named after Micheal Jordan the famous basketball player. Ben is the youngest child and his parentage came into question when it was discovered that Shirley had a brief fling with Chang. When Shirley went into premature labor during Anthropology class, Britta and Chang helped Shirley deliver the child safely. Chang conceded the baby couldn't be his child since all Chang baby's are born with tails and he didn't have one. To thank him for helping her through the birth Shirley named the child after him.
In her first year at Greendale, Shirley was good friends with Gary, a student from Finland known for being a buzz-kill and a generally unpleasant person to be around. Nevertheless, Shirley considered him a good friend and would often try to get the other him included in study group's activities. He ended up transferring at the end of the year much to the celebration of everyone but Shirley.