Troy stop! Don't become this person again! This isn't the real you, this is the arrogant jock that totally ignored the only people that truly liked him for non-superficial reasons but weren't allowed to say anything because her parents were bigots!
In the study group's first year together at school, Annie had a crush on Troy, having been infatuated with him since they both previously attended Riverside High School. Annie was one of many admirers of Troy had while he was the star quarter-back of the football team. Before graduating high school they both ended up losing out on scholarships offered to them due to poor choices they made. With limited options they were both forced to attend Greendale Community College. Annie saw this as an opportunity to finally be noticed by Troy and tried several times to reveal her feelings to him but he remained oblivious. Eventually she gave up realizing he would never be as fond of her as he is his best friend Abed Nadir. She moved on to pursue other possibilities although Troy became of aware of Annie's past feelings for him. However, he decided not to pursue her romantically and has instead forged a good friendship with her. Troy is portrayed by Donald Glover and Annie is portrayed by Alison Brie.
During their freshmen year at Greendale, Annie helped Troy in a number of activities in order to get closer to him helping him prepare for a date and studying for astronomy. It's revealed that she lost her scholarship to an ivy league school due to an Adderal induced freak out she had in high school and that Troy lost a chance at a football scholarship when he injured himself trying to perform a keg flip at a party. She attempts to convince him not to play football again and Jeff calls her out over her selfish motivations behind this. Jeff also correctly guessed that she took all his classes and it's implied she only came to Greendale because of Troy. Eventually, Annie gets tired of not being noticed by Troy and moves on, particularly after realizing she could never take the place of Abed in his heart. She starts dating Vaughn Miller which upsets both Jeff and Britta. Jeff makes Troy see how attractive Annie is so he could hit on Annie and break up her and Vaughn. Later, Annie and Shirley team up to get revenge on Señor Chang on behalf of Troy and Pierce who he had humiliated but the plan ends up backfiring on them. Troy receives a pet monkey as a gift from Abed which he ends up calling "Annie's Boobs" over Annie's objections.
''Admit it. We went to school together for four years and you didn't even know me.
Yeah but I know you now. You're Annie. You like puzzles and little monsters on your pencils and some guy named Mark Ruffalo. You're a fierce competitor and a sore loser and you expect everybody to be better than who they are and you expect yourself to be better than everyone... which is cool.''
During their second year at Greendale, Annie is dealing with lingering feelings for Jeff after the kiss at the Tranny Dance and Troy's friendship with Abed becomes a full blown bromance that takes up most of his time. When Troy, Abed and Annie break into the Alan's office, Troy becomes distracted by Annie's unintentional jiggling. When she later instinctively goes to chloroform Jeff, Troy stops her. On Troy's birthday, they share a heart to heart conversation and Troy comforts Annie after she has an identity crisis reassuring her that she is a good person at heart. On Christmas, Troy and Annie steadfastly support Abed after Duncan attempts to put an end to therapeutic journey to discover the true meaning of Christmas. When the study group tries to help Fat Neil out of his depression by playing a game of Dungeons & Dragons with him, she accidentally grabs a character sheet Abed as the Dungeon Master had created specifically with Troy in mind called "Hector the Well-Endowed". At the end of the year annual paintball assassination game Annie, along with Abed, joins Troy's paintball commando squad. She helps him lay a trap in the library for the invading City College Storm Troopers.
At the start of the 2011 Fall semester at Greendale, Troy and Annie became roommates. At Troy's housewarming party for the new apartment he shared with Abed, Annie accepted an invitation to move in with them. Alongside the rest of the study group (sans Jeff who pretended to be sick) Troy helped Annie pack up her belongings. Annie had some reservations about moving after she witnesses a few of Troy and Abed's childish behavior. Eventually she learned to accept their quirks and even joined in on their antics. Sometime after settling into the apartment, Annie accidentally broke Abed's special edition Dark Knight DVD. Troy accidentally learned about it and helped Annie cover up her mistake. While helping Britta avoid her ex-boyfriend Blade, Annie realized Troy had strong feelings for Britta. She later sets them up on a lunch date much to Abed's annoyance. In the middle if the school year the study group is expelled when they caused a riot to occur in the cafeteria. Troy raises everyone spirits Shen Annie and the others start to get depressed over their situation. Eventually the study group is allowed to return but in doing so Troy is forced to join the Greendale Air Conditioning Repair School. Annie and the study group are bid him a tearful goodbye as he moved out of the apartment and into the school dorms. A few months later during the summer Troy managed to get free from the AC school and Annie and the the others happily welcomed him back.
In the study group's fourth year at Greendale, Troy and Annie were both worried about Abed. It was possibly the last year the group might be together. They later went to Hawthorne Manor along with the rest of the group to free Pierce who was trapped in panic room. During the rescue mission, Troy mentions to Annie that he enjoys talking to her. When Chang returned to the Greendale campus claiming to have "Changnesia", Jeff had Troy and Annie investigate what happened to him. Troy is excited to do this and names the team "Partner and Hollihan". Annie has a hunch that Chang had been working at a place called "Sullivan's trout farm". With Troy playing "bad cop" to Annie's "good cop" they interrogate Sullivan who confirms this. Later, Annie and Shirley remind Troy and Britta about the upcoming anniversary to their first date. Near the middle of the school year, Jeff graduates early and Troy and Annie attend his graduation ceremony along with the rest of the group.
"History 101": Troy and Annie try to calm Abed down about the upcoming school year.
"Paranormal Parentage": Troy and Annie, along with the rest of the study group, try to free Pierce from his panic room inside his mansion.
"Conventions of Space and Time": Annie attends InSpecTiCon with Troy, Abed and Britta but spends most of the time in the hotel pretending to be married to Jeff.
"Cooperative Escapism in Familial Relations": Troy makes fun of Annie complaining about Thanksgiving with her family. Then Troy, Annie, Pierce and Abed spend Thanksgiving at Shirley's house. They find her relatives hard to deal with and want to leave. Annie fakes menstrual cramps but Shirley's sister in law is a gynecologist. Troy suggests they eat two year old dip that's Abed brought but is in the garbage.
"Intro to Felt Surrogacy": The Study Group takes a balloon trip and ends up stranded in the woods. They reveal their most terrible secret. Annie admits she let Professor Noel Cornwallis rub her feet for answers to a test. Troy admits he started the Greendale fire of 2003 by burning an anthill.
"Basic Human Anatomy": Annie and Shirley remind Troy and Britta about their upcoming anniversary to their first date.
In 2013 Troy and Annie unexpectedly reunited with the rest of study group (sans Pierce) at Greendale. Unsatisfied with how their lives turned out after graduating Troy and Annie re-enrol at school alongside true friends to find new purpose. The school year began with Annie starting a protest against the teachers over a grading scandal. Troy and Britta supported Annie in her efforts as did a mob of other angry students which led to the creation of a new school organization. Dubbed the "Save Greendale Committee" it was dedicated to repairing student/teacher relations and improving campus life. Troy and Annie joined the ranks alongside their friends in the study group. One of their first assignments was dealing with the return of the "Ass Crack Bandit". When Troy becomes the next victim of the Ass Crack Bandit Annie is on the crime scene forensics team canvassing the area he was assaulted for evidence. News of Pierce's death put a halt to the investigation as Troy and Annie joined the study group in grieving their departed friend. Troy and Annie received individual bequeathals according to Pierce's will. While Annie got a tiara, Troy got the opportunity to win Pierce's fortune if he chose to complete a trip around the world in a sail boat. Troy accepted the challenge to the shock of his friends who nevertheless supported his decision. Before his departure Abed organized a campus wide game of Hot Lava in his honor which Troy and Annie competed in. Afterwards the study group said their goodbyes to Troy. Annie reminisced about their time in high school and Troy told her he wished they had be one friends earlier. Annie watched alongside their friends as he boarded a rig with the sailboat on it and departed the Greendale campus.
Troy and Annie were meant to be the junior romance on the show contrasting the main one in Jeff and Britta by being more sweet and innocent in comparison. Unlike Jeff, who aggressively pursued Britta, Annie was to secretly pine away for Troy, hoping he would eventually notice her. As the show progressed, however, Troy's relationship with Abed became more central to the development of his character then Annie's one-sided romance with him. On top of that, Annie's character managed to generate compelling UST and a good rapport with Jeff. Both the Jeff/Annie and Troy/Abed combinations quickly superseded the original pairings that were envisioned and Troy and Annie's romantic plot was eventually dropped.