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. Annie was one of many admirers of Troy had while he was the school's star quarter-back. Before graduating high school, they both ended up losing out on scholarships due to poor choices they made and 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. Frustrated, she gave up and moved on and while Troy has since became aware of Annie's attractiveness, he has not pursued 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 thier 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.
Abed invites Annie to move in with him and Troy in their new apartment. Annie agrees but on moving day has some reservations about it after witnessing a few of their childish antics. After settling into the apartment, Annie accidentally breaks Abed's special edition Dark Knight DVD and Troy helps her cover up her mistake. While helping Britta avoid her ex-boyfriend Blade, Annie realizes Troy has strong feelings for Britta. She later sets them up on a lunch date much to Abed's annoyance.
When Troy is forced to join the Greendale Air Conditioning Repair School, Annie along with the rest of the study group bid a tearful goodbye to him. They all later happily welcome him back when he returns to Greendale after having gotten his freedom from the A/C school.
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 Hullihan". 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.
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.