Since I can't help picturing Jeff/Annie together, I wrote up another faux-script scenario! In the final bit most of the original study group appears, continuity be damned. Otherwise takes place after the events of season 6.
BRITTA sits in front of a computer at GREENDALE. JEFF enters.
JEFF: What's up?
BRITTA: Hey! I'm chatting with Annie.
ANNIE appears on BRITTA's screen throughout. The kitchen of ANNIE's apartment is visible behind her.
JEFF: Hey, how's the internship going?
ANNIE: It's good. Mostly I'm in charge of baggies. But my supervisor said next week I can throw up at a crime scene!
She continues to talk, but can't be heard over a newly switched-on vacuum cleaner. She scowls and shouts at someone off-screen.
ANNIE: Do you have to do that right now?!
ANNIE's camera spins around to show her apartment. Several tall, beefy, handsome young men are present – vacuuming, folding laundry, baking.
ROOMATE 1 switches off the vacuum cleaner.
ROOMATE 1: Sorry, Annie.
JEFF (muttering to BRITTA): These are the roommates she was complaining about?
BRITTA: Yes. Hi Jared!
She waves at the roommate who is folding laundry. He waves back.
JARED: Hi, Britta.
BRITTA (whispering, hands clasped, eyes shining): Jared's my favorite.
ANNIE's phone spins back around to show ANNIE rolling her eyes.
ANNIE: As I was saying –
A hand enters frame, holding a plate with a warm blueberry muffin. The muffin bearer is not otherwise visible but his hand sure is handsome.
ROOMATE 2: Annie, I made muffins –
ANNNIE: Can't you see I'm on the phone?! GOD!
ROOMATE 2: Sorry, Annie.
ANNIE: Can we talk later? It's a zoo in here.
BRITTA (sweetly): Any time.
ANNIE turns around to yell at her roommates as she switches off her camera. BRITTA minimizes the chat window, revealing that her wallpaper is a screen grab of Jared matching socks.
BRITTA: He's my favorite!
JEFF: UGH.
Cut to JEFF at home, staring at his phone. It's now evening. He's being gnawed by fear and jealousy. He types and deletes a text, types it again, and finally sends. The text floats above him. It's sent to ANNIE.
JEFF (text): What if I visited you in DC?
ANNIE's response, three dots of doom, floats under his text, then vanishes.
JEFF (text): Unless that would be weird
JEFF squinches up his face, certain he's just made a terrible mistake. The three dots of doom reappear. He can't bear to look at his phone. After a moment, a message from ANNIE arrives.
ANNIE (text): What if we found out?
JEFF is excited. JEFF is also terrified. JEFF is going to Washington.
The camera shows ANNIE's apartment. ROOMMATE 1 is washing dishes and ROOMMATE 2 is scrapbooking. ANNIE's voice can be heard approaching as they climb the stairs.
ANNIE: …I just need to change quickly, and then we can go to dinner.
ANNIE and JEFF enter. The vibe is awkward.
ROOMMATES (in chorus): Hi Annie!
ANNIE: Hiii!
ANNIE goes into her bedroom and closes the door. JEFF gives the roommates a half-wave and immediately pulls out his phone.
ROOMMATE 1: Ooh, where yah going?
JEFF: Uh…Davio's?
ROOMMATE 2: Sick! That's where my parents take me when they visit, too.
ANNIE reemerges, having changed from work clothes to a navy-blue shirtdress.
JEFF: Ready to go?
ROOMMATE 1: Have fun with your –
ANNIE: FRIEND! Goodnight!
Cut to Davio's, where the vibe is even more awkward. ANNIE and JEFF make attempts to talk, but keep bumping into each other's sentences. They take refuge in the menus. This is not going well. The WAITER approaches.
WAITER: Are you and your daughter ready to order, sir?
ANNIE: That's enough.
She slams down her menu.
ANNIE (yelling): This is not my father. We are on a date! And it's fine!
She rises from her seat. Originally yelling at the WAITER, she's now self-righteously addressing the whole restaurant, which has fallen into a shocked silence.
ANNIE: We're two consenting adults! And you know what? (Waving her arms expansively) I CONSENT!
ANNIE becomes aware of everyone's attention. She shrinks, tucks her skirt under her legs, and sits back down silently.
WAITER (squeaking): I'll give you a minute.
The WAITER scurries away. Background noise resumes in the restaurant, though it's mostly about her. ANNIE has her elbows on the table and her palms pressed into her eyes. JEFF, surprisingly, starts to laugh unrestrainedly.
ANNIE: How can you laugh? That was sooo embarrassing. I can't believe I screamed like that!
JEFF: I'm glad you did. Because now I know, officially, that this is a date.
ANNIE peels her hands from her eyes and gives JEFF a watery smile. The WAITER approaches cautiously, carrying a bottle of wine.
WAITER: A gift from that table over there.
As the WAITER pours, JEFF and ANNIE look to the corner to see a couple dining – the woman, a nicely-preserved forty, and the man, definitely twice that. The couple toasts JEFF and ANNIE. ANNIE waves and mouths 'thank you'. The WAITER departs and ANNIE picks up her now-full wineglass, using it hide her face from the couple in the corner.
ANNIE (whispering, almost helpless against laughter): He's so old!
JEFF is examining the wine bottle.
JEFF: This wine is younger than you, maybe I should ask it for a date.
ANNIE: Jeff!
ANNIE smacks JEFF's arm. The tension is broken. Now they talk easily and laugh a lot. It's a very good date! At the end, JEFF pays and then guides ANNIE towards the door, his hand on the small of her back. The WAITER shrinks back when ANNIE passes him, quivering. The May-December couple is feeding each other romantically. Just before leaving, JEFF turns back to the restaurant.
JEFF (shouting): NOW WE'RE GETTING ICE CREAM!
ANNIE shrieks and pulls him into the street.
Cut to the street outside ANNIE's apartment. JEFF has his sleeves rolled up. He and ANNIE are just finishing their ice cream cones. ANNIE stands on her front stoop, turning her face up to JEFF's.
ANNIE: I had a really fun time tonight.
JEFF: Me too.
ANNIE and JEFF kiss. The kiss deepens. She breaks off the kiss to ask a question.
ANNIE (breathlessly): Do you want to go up?
JEFF: Yes. I do. Badly. But I don't want the first time we…go up…together…to be one inch of drywall away from five Jareds. Is that okay?
ANNIE begins to smile. She swishes her shoulders back and forth, pleased with her own news.
ANNIE: They're out. They went to a Shania Twain concert.
JEFF (surprised): Really? (then intrigued) Reeaally?
ANNIE (smiling widely): Really.
Cut to an intense makeout session up the stairs, pinballing off the walls. Shoes are kicked off. Somebody is unbuttoning something as fast as they can. JEFF and ANNIE tumble into ANNIE's room. The door slams shut behind them.
COMMERCIAL.
JEFF and ANNIE are lying side-by-side in ANNIE's bed, staring at the ceiling, panting heavily, lit only by streetlights. ANNIE's hair is loose and the sheet is pulled over her chest. JEFF is similarly naked and tangled in a sheet.
JEFF: Wow.
ANNIE: Wow. I mean…
JEFF: Wow.
ANNIE's gaze wanders around the ceiling. She uses a tone of fake remoteness, as if the question just occurred to her.
ANNIE: I know you can't really assign a grade…
JEFF: A plus.
ANNIE squeezes her eyes shut and does a lying-down version of her stupid happy dance. Then she opens her eyes and tips her head on the pillow, finally looking at JEFF. He turns and looks back at her.
ANNIE: …Wanna do it again?
JEFF: Ye –
Before he can get out the whole word, ANNIE is on top of him.
JEFF: OH, what, now, okay –
The camera tracks away, giving them their privacy.
The next morning, ANNIE and JEFF are sitting at the kitchen table, drinking coffee, reading their phones. Sometimes they make eye contact, smile, and quickly look away. ANNIE is in cute jim-jams. JEFF is back in his clothes from the day before.
JARED enters.
JARED: Shania was a revelation! Oh hey, I'm Jared.
ANNIE: This is Jeff. He's mmmyyy…
ANNIE flounders. JEFF sticks out a hand for Jared to shake.
JEFF: What up man, I'm Annie's boyfriend.
JEFF and ANNIE smile at each other. ANNIE looks shy and pleased. JEFF looks content.
JARED: Pleasure to meet you. Who wants waffles?
JARED begins to fix waffles, singing "MAN! I feel like a woman!". Jeff and Annie go back to reading their phones, but now they're holding hands on the table.
At the airport, JEFF and ANNIE kiss goodbye.
ANNIE: I'll be back in four weeks.
JEFF: I'll be there.
They kiss again. JEFF walks through security. They wave and smile.
Four weeks pass.
JEFF, BRITTA, TROY, and ABED, are hanging at BRITTA's bar, chatting and relaxing. An alert sounds on JEFF's phone.
JEFF: Oh, Annie's flight just landed. I'm picking her up at the airport.
He starts to gather his things. Meanwhile, the camera pushes in on BRITTA. The wheels are turning in her mind. Sound effect: PING!
BRITTA: Oh my god! Jeff likes Annie!
JEFF: What?!
ABED: Called it.
TROY: What?
BRITTA: You know how he's been making goo-goo eyes at his phone lately? (Britta wiggles her fingers in the air and makes a 'gag' face.) He didn't even hit on that redhead! Jeff likes Annie! Why else would he (with great disdain) pick her up from the airport?
JEFF: It's not – I'm not – we wanted to tell you together.
BRITTA: 'Together'?! (A pause, raised eyebrow.) Is she even getting a hotel?
JEFF remains silent.
BRITTA: Oh my god! Jeff is defiling Annie!
TROY: Cool! Wait, which Annie?
ABED: Our Annie.
TROY: You're defiling our Annie?!
JEFF: I'm not defiling Annie! She's defiling – nobody is being defiled! We're dating!
BRITTA, ABED, and TROY, leap up from the table and emote around the room, making a shared noise of shock and confusion.
BRITTA: Now this I've got to see. We're going with you!
At the airport.
ANNIE is just emerging from security, carrying her bags. JEFF is standing a little ahead of the group, wearing a hangdog expression. BRITTA, ABED, and TROY are standing shoulder-to-shoulder, watching carefully. Initially, ANNIE dances with delight and runs towards the group for a hug, but then she notices JEFF's face. She stops dead and frowns at him.
ANNIE: You told them?!
JEFF (guiltily): They figured it out.
ANNIE rolls her eyes.
ANNIE: Fine. So you know. Then I guess we can do…this.
She and JEFF are standing in profile before the line of their friends. They slowly lean towards each other, then share a quick, chaste peck.
BRITTA, ABED, TROY: AHHH!
BRITTA: What's the word for so angry you're almost happy?!
TROY: Horny.
BRITTA: I think I speak for all of us when I say, we're horny that you kept this secret from us!
ANNIE and JEFF face the group, holding hands.
ANNIE: Then you'll be even hornier to hear – (everyone pauses and makes a face like they tasted something yucky) – I'm moving back to Greendale!
Now when they shriek, it's in happiness, and the group comes together in a hug, bouncing up and down. As it breaks apart, JEFF takes ANNIE's bags, and ANNIE and BRITTA hang at the back of the group.
ANNIE: Is this okay? Are we okay?
BRITTA (sincerely): Of course. I mean, if you're happy. How's the…you know?
ANNIE: Sex, Britta? You can say it. (ANNIE smiles, embarrassed.) It's fine. (Confessing.) I'm working on being less selfish in bed.
BRITTA: …Wuh?
ANNIE: Oh! I brought you what you asked for!
From her handbag, ANNIE takes out a box of dryer sheets.
ANNIE: He said he didn't know why you wanted them, but sure.
BRITTA takes the box and sniffs it deeply.
BRITTA: I'm going to smell like Jared!
BRITTA throws an arm around ANNIE's shoulders and hugs her, smiling.
BRITTA: Welcome home.