What do you think happened/will happen to Jeff and Annie after season 6?
If you’re asking me for super-detailed scenarios, you’re asking the wrong person. There’s a reason I beta-read fanfiction, and don’t write it. :) But I can probably ramble for a few paragraphs, at least.
Basically, I think they stayed in touch and talked a lot while Annie was in DC. Their goodbye at the airport was WAY too casual and calm and smiley for ‘I’ll talk to you in ten weeks, person whom I’ve been in unrequited love with for the past six years’; it was more like ‘I’ll text you when I land/talk to you soon/see you when you come visit me in a few weeks/pick you up when you fly back to Colorado’. When Annie did get back I think she was probably like, listen buddy I have waited for six years and we are not getting any younger, NOW KISS ME. And he obviously was like, okay then if you’re sure, and kissed her.
So they’ve been together for a year now, more or less, and in addition to being in a healthy and supportive relationship, Jeff has been in therapy with Annie’s encouragement to deal with his shit and to figure out if he wants to keep teaching or do something else with his life. The important part is, he’s starting to believe he deserves to do something with his life that makes him happy, partly because Annie believes that, and she’s the smartest person he knows, so he figures he should probably listen to her. They’re happy and love each other and pretty much expect to stay together. Annie’s not bothered about marriage because she knows Jeff has issues and anyway she’s learned to plan ahead while still taking things one day at a time, but Jeff’s already started thinking about asking Annie to marry him, someday. He’s still not totally convinced she’d say yes, but she will, eventually.
They hang out with their Greendale friends when they can, and of course Britta and Annie are still roommates which is somehow (weirdly) still working really well. Troy is definitely back from his world cruise by now, and after a brief stay with Annie and Britta in Apartment 303, he probably made his way to L.A. and is living with Abed, where they’re watching TV and making movies and just generally being their awesome selves.
The remaining Greendale Seven (plus Frankie and Craig and Duncan) all have a group text/chat thing and send each other photos and have weird conversations all the time. (Chang isn’t part of the group text/chat thing because Jeff threatened to murder anyone who even hinted to Chang that it existed, and Elroy is technically part of it but he almost never participates. Occasionally he’ll send photos of weird sculptures he comes across.)
For further reading, may I recommend a handful of my favorite post-S6 fics:
Social Media Ficlets by @imadiebywerewolf: Some snippets of Jeff and Annie’s relationship unfolding on various social media. Set post-S6.
You’ll See How Well We Rhyme by @hello-wright-or-wrong: “It’s probably why he’s felt so envious of Annie, going out and changing her life, chasing something new and better – and it’s probably why it was so easy to come up with alternate scenarios for the future after she got her internship. There’s got to be something better out there for him too.” Post S6 finale
No Season Can Contain It, also by @hello-wright-or-wrong: “We’re starting some really strange holiday traditions,” Jeff teases, and she can’t really argue. Set post-S6.
Everybody Knows by @jeffwik: When he learns Annie won’t be returning to Greendale in the fall after all, Jeff takes dramatic steps in an attempt to move on. (Spoiler alert: it doesn’t work.)
Prove Me Wrong by @pepperf: Five “season 7” scenarios that were all in Jeff’s head, and one that actually happened. (and its follow-up, Supporting Evidence by @pepperf: “Look, I’m just going to come out and say this: Annie and I are together now." "Well, duh.”)
Emotional First-Aid For Amateur Busybodies by @pepperf: School’s out and Annie’s going away and nothing really matters. Which doesn’t explain why he’s awake at 2 a.m. worrying about it all. (This is really only set in the week between the finale and Annie going off to DC, but it sets the tone for how Jeff and Annie intend to move forward.)
Five Times That Annie Seduced Jeff, And One Time She Got Distracted And Forgot (But It Worked Anyway) by @pepperf: I’m just going to let that title speak for itself. (This is mostly not post-S6, but I love the one part that is post-S6 so much I’m including it.)