jeff and annie 2x09 community icons

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The exact moment it was game over:

Annie: Oh, my gosh. You're right. Simmons is so good at using his inherent magnetism to sell his points, and here I am, like a spinster librarian with my hair pulled back. 😬

Annie: What do you think? 😍😍

Jeff: Uh, yeah. 😍😍😍

Annie: Thanks. 😍😍😍

Annie and Jeff: 😳😳

Shirley: Be careful! Abed thinks you two are going to kiss. 😂 Ridiculous! 🤣

Jeff: Us. Kissing. 😂 That is ridiculous. 😍

Annie: Totally. 😍😂

Jeff: 😍😍

Annie: 😍😍

But then she grew up. And it got more appropriate because she came to be in her twenties, and she was more mature and older (things which I have previously stated before).

But I think the whole point of Jeff x Annie in the series was that, while they may have been meant to be, and been True Love...they were not meant to be yet. She still had a life to live and experiences to have, which in the end of the series, he decided he didn't want to hold her back from.