|Annie and Vaughn dated in the study groups freshmen year at Greendale. She enjoyed his free spirited way of life which was opposed to her own rigid way of living. In contrast to her one-sided crush on Troy who often 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 he dated her. The two happily dated for a few months and Vaughn's nickname for her was "Mountain Flower". 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 between other couples leads to an unexpected pairing. 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 decides to pursue someone more attainable and finds herself attracted to Britta's ex-boyfriend Vaughn Miller. Due to the acrimonious way that relationship ended, she decides to ask Britta for permission to date him. Although Britta gives her consent and seems fine with it, she is secretly uncomfortable with the situation. She subtly manipulates Jeff by playing on his overprotectiveness of Annie and dislike of Vaughn. He considers Vaughn a "gate way douche bag" who will cause Annie to lower her standards and let any jerk date her.
When Jeff and Britta catch Annie and Vaughn canoodling on the campus quad, his theory is somewhat proven correct when Star-Burns witnesses the scene as well and makes a crude comment about Annie. An annoyed Jeff then decides to break the pair up for Annie's own good with Britta agreeing to help. They decided to enlist the help of her original crush Troy to give her an alternative and more preferable romantic interest. They find him in the study room and try to get him interested in Annie. An obtuse Troy didn't get their hints until Jeff took him aside and whispered a few ribald observations he himself had about Annie. Britta pushes him further towards their intention of having him disrupt Annie's new romance by adding that the only reason his former crush is dating Vaughn is to get Troy's attention.
Later, Troy seeks put Annie and finds her in the student lounge by herself. He starts to hit on her but she misunderstands his actions and is confused by his odd behavior. Vaughn then appears having left Annie alone for a bit to get them some ice cream. 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. Annie admits to having a crush on Troy once but she denies she feels that way anymore. Vaughn is hurt by the revelation feeling that once again he's been betrayed just like he was when he dated Britta. He breaks up with Annie and leaves in a huff. Troy continues to hit on her but she angrily rejects his advances. He then lets it slip that Jeff and Britta set this whole thing up. Annie then goes to find the pair in the study room and tells them off for meddling with her love life.
The next day at the study group meeting, Jeff and Britta try to apologize to Annie. Proclaiming themselves the groups "Greendale parents", they state they were only looking out for Annie's best interests. Still irate, Annie refuses to accept their apology and tells them to stay out of her affairs. Britta then drops her cool façade and angrily replies that if Annie wants to be treated as an adult she shouldn't steal her old boyfriend. Both Annie and Jeff are shocked at her statement realizing her true reasons for her actions. Britta then calls out Jeff for his own selfish reasons for not wanting to see Annie and Vaughn together citing the kiss he and Annie shared while on the debate team. This leads into a series of awkward exchanges amongst the rest of the study group over possible romantic entanglements within the circle of friends. The discussion is then interrupted when everyone hears music playing outside the library.
Upon exiting the building, they find Vaughn and his drummer performing a song. It's 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 embraces Vaughn after its over. Annie then tells the study group she is going off with Vaughn to see a cloud shaped like a pumpkin. Britta, along with Jeff, give their approval now that they've seen how sincere Vaughn is ("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. While its an opportunity for him to become the next Hackey Sack super star like Yngwie Macadangdang Junior, it also means he has to move to Deleware.
Wanting to follow Professor Whitman's example of "Living in the moment", Annie decides 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").