|Annie and Vaughn dated in the study groups freshmen year at Greendale. She enjoyed his free spirited way of life which was a contrast to her own rigid way of living. In comparison to her unrequited feelings for Troy who ignored her obvious attraction to him, Vaughn noticed her and lavished her with his attention. Annie for her part was more comfortable with his grand romantic gestures than Britta was when she was briefly seeing Vaughn. The two happily dated for a few months until a school transfer for Vaughn led to them breaking up. The pair officially became a couple in the Season One episode "Romantic Expressionism". Annie is portrayed by Alison Brie and Vaughn is portrayed by Eric Christian Olsen.|
In the study groups first year together, a series of romantic developments led to a few unexpected pairings. After the Winter break, Annie's feelings for Troy start to wane after realizing that she could never compete with Abed for his affections. She decided to pursue someone more attainable and found herself attracted to Britta's ex-boyfriend Vaughn Miller. She approached him on the campus quad and Vaughn flirted with her by showing off his guitar playing skills. Due to the acrimonious way his relationship with Britta ended, Annie asked her friend for permission to date him. Although Britta gave her consent she was secretly uncomfortable with the situation. She subtly manipulated Jeff by playing on his overprotectiveness of Annie and dislike of Vaughn. He considered Vaughn a "gate way douche bag" who would cause Annie to lower her standards and let any jerk date her.
His theory was somewhat proven correct when Star-Burns witnessed Annie and Vaughn canoodling on the campus quad and made crude comment about her. Jeff and Britta conspired to break the pair up for Annie's own good. They enlisted the help of Annie's original crush Troy to give her an alternative and more preferable romantic interest. After convincing him Annie was still interested Troy found her in the student lounge by herself. Much to her confusion he started hitting on her when Vaughn showed up. Troy is dismissive of Vaughn's cheerful greeting to him and implies that he and Annie are together claiming that shes been in love with him since high school. Vaughn is hurt by the revelation feeling he had been betrayed just like he was when he dated Britta. He broke up with Annie who discovers from Troy that Jeff and Britta put him up to this. Annie then found the pair in the study room and told them off for meddling with her love life.
The next day at the study group meeting, Jeff and Britta tried to apologize to Annie who was still upset and refused to accept. Her rebuff caused Britta to get angry and admit she was never fine with Annie dating Vaughn. Britta then called out Jeff for his own selfish reasons for not wanting to see Annie and Vaughn together citing the two of them shared while on the debate team. After an awkward discussion amongst the study group about possible pairings within their circle was interrupted when music was heard playing outside the library. Everyone exited the building and saw Vaughn and his bands drummer performing a song. It was an ode to Annie called "Annie's song" which Vaughn sings unabashedly. The study group and Annie are moved by the heartfelt performance and she reconciles with Vaughn.
Britta, along with Jeff, gave their approval after Annie tells everyone she is going off with Vaughn to see a cloud shaped like a pumpkin ("Romantic Expressionism"). The two date for several months and Vaughn is shown to have sent Annie a single rose on Valentines Day ("Communication Studies"). At the end of the school year, Vaughn is offered a chance to join a prestigious Hacky Sack university. He tells Annie the news while she is at an end of the year keg party being held in Abed's dorm room. At the school he hoped to become the next Hackey Sack super star like Yngwie Macadangdang Junior. The only drawback was that he had to move across the country since the school was located in Deleware. Annie supported Vaughn's ambition and in the spirit of Professor Whitman's ideas of "Living in the moment" decided to transfer with him.
That night at the annual Transfer Dance formal being held in the cafeteria, Annie lies to the group saying she is leaving with Vaughn to go see his new school just for the summer. She only tells Jeff confidentially the truth about her decision. While he is sad to see her go he wishes her good luck. Later, she and Vaughn say their goodbyes to the group and depart. However, at the last minute she changes her mind about going and decides that Greendale is where she belongs. Returning to school with her luggage in hand, she made her way back to the cafeteria only to find Jeff outside. The two have an intimate discussion over their romantic troubles which eventually leads to them sharing a passionate kiss ("Pascal's Triangle Revisited").