One guy on reddit explains Abed/Annie as a ship.
Annie romanticizes her crushes and tries to manipulate them into happening—She had whole scenario laid out in her head of how Troy would take her on a date, and she’s always trying to ‘set Jeff straight’— she does the exact thing that Shirley accused Britta of in Season 1: “Stirring in sweetener”. Finally in 209, Jeff tells her, “When you love someone, you have to take them as they are”. Uptight Annie doesn’t know how not to prepare, and try to be in control of any given situation (also reflected in Annie’s Caroline Decker monologue from 210).
Conversely, Abed’s arc is about being able to relate to life around him, using tropes or characters. Increasingly throughout the series we see Abed accidentally succeeding with Annie in this way, until eventually he actively seeks for her to take part in his more recent fantasies, always personifying her as the damsel. This is significant since Abed maintains that “People always try to help me […] then when they find out they can’t, they stop talking to me” and “It’s easy to change for other people”, but that “People have to get [him]”. Abed doesn’t want someone to “fix” him, but to understand him—and Abed is the first instance of Annie actually not trying to fix or control anything, and rather just going with it.
These two themes mean that there’s a lot of potential character payoff in the Abed/Annie pairing. Abed succeeds in connecting with Annie in the very way which represents her character struggle— by getting her to suspend her disbelief, live in the moment and ‘be immature’. Annie succeeds in connecting with Abed in the very way that is his biggest struggle—by reciprocating and understanding his tendency toward escapism. The idea that they might develop a unique and eccentric bond under the safe guise of playing characters is far more interesting and appealing than Jeff & Annie’s slow slide into Jim and Pam 2.0.
By the way, as you can tell I love speculating about all this stuff, so if you disagree don’t expect any bad blood from me, I’m just here to gab. :) I will not go Big Cheddar on you. [x]