Jeff hated Family Day. Ever since that first God awful one with Pierce’s (ex) step-daughter, he’d started to hate it even more. The only reason he kept showing up to the dumb Greendale holiday every year was because Annie started organizing it. (Not because he was in love with her, but because he was supporting a member of the group, BRITTA AND SHIRLEY.)
To be fair, the Family Day Activities kept getting better every year, and, even though Jeff would never admit it, he kinda started to enjoy it a little bit. Hell, maybe next year he’d even bring his mom. Maybe, he’d even introduce her to his friends. He’d definitely introduce her to Annie, though. His mom and Annie would love each other, and that’s the only reason he’d introduce them. Not because he was already mentally preparing for his and Annie’s wedding. Nope. Definitely the first one.
Even though he started to enjoy Family Day itself, he still couldn’t stand the dance afterwards. The Dean loved planning it, and that never went well. You’d think after the fireworks exploding inside the cafeteria, the Dean would have let someone else take over the planning. As Jeff was leaving, he heard muffled sobbing from the study room. He would have kept walking, but he noticed that the person sobbing was Annie.
He quietly slipped into the study room and shut the door behind him. Annie looked up and immediately tried to pretend like she hadn’t just been crying.
“Jeff, what are you doing here? I thought you left already.”
“I was just heading out, but I heard you crying. Is everything okay?”
“Yeah, I’m fine. It’s nothing.”
“No offense Annie, but it’s clearly not nothing. Your face is wet, and your eyes are redder than Britta’s when she gets high. Do you wanna talk about it? If you don’t that’s fine, but don’t try to pretend it’s nothing.”
“It’s just…I ask my family to come to Family Day every year, and in the hopes that they actually show up, I try to make the events as amazing as possible so they see how well I’m doing.”
The tears started to fall again, and Annie’s breaths started to get shaky.
“Bu-but, they never come. Not ev-even my dad or my-my brother. I just- Am I really that awful? That-that they won’t even show up for one dumb holiday? I- I know it’s dumb, but I feel so alone, and seeing everyone with their fa-families just rubs salt in the wound and-”
Annie couldn’t even get the rest of the sentence out before she started sobbing again. Jeff ran over, pulled her out of her chair, and wrapped her in a hug.
“Listen, Annie. I wish your family saw the amazing person you really are. You’re kind, smart, driven, and passionate. You’re going to be successful and have an amazing life. You could literally do whatever you wanted. So many people would kill for a daughter like you. And you’re not alone. Pierce, out of all people, said something during the first Family Day that’s stuck with me. If you have friends, you have family. You have Troy and Abed, Britta, Shirley, and me. Hell, even Pierce when he’s not being completely awful.”
Annie pulled out of the hug and wiped her eyes.
“That might be the best Winger speech you’ve ever given.”
“Well, it was all true.”
“Thanks, Jeff. It actually helped a lot. I should probably head to the dance now, though. Someone has to be in charge of keeping the Dean from setting something on fire or causing an explosion.”
Annie flashed him a small but genuine smile and then left to go keep the Dean from destroying the school. Jeff smiled sadly to himself. Annie’s family abandoned her, but she still held out hope. He knew Annie was resilient and stubborn as hell, but this was a whole new level. He never wanted to see Annie that sad again, and he was going to do everything in his power to make sure she wasn’t alone next family day. His mom really would love Annie. And would treat her like a daughter. He knew she’d always wanted a daughter, anyway. As he was thinking about how to make Annie happy and how awful it was to see her so upset, he realized, maybe, just maybe, it was time to admit that he was a little in love with her.