Jeff can’t pinpoint in his mind the exact moment he fell in love with Annie. He remembers the first time he realized he liked her, the time she kissed him at the debate, but love? That’s a much more complicated beast to tame, especially for him. He knows he felt jealous when Annie had a crush on Rich, he knows he felt ashamed when he realized how much he hurt her, and he knows he felt something when she gave the group her own variation of a “Winger Speech”.
He isn’t sure when it started, but he knows he’s drowning in it now.
Being Jeff Winger, he is terrified of what this may mean. Commitment isn’t his strong suit. But he’s trying; he’d do anything for her.
The first time he said it, he knew she couldn’t hear him. Jeff had a long week at work and his apartment reflected that fact. Dirty dishes, unfolded laundry, and dust covered every surface. Annie had just started her new job and was so sucked into it that she didn’t notice the mess until Friday night.
“Why does it look like a bomb went off in here?” Annie asked, arms crossed.
Jeff glanced away from the papers he was grading and raised his eyebrows. “I guess I didn’t realize it was this bad.”
Annie shook her head and disappeared down the hallway. She came back a few seconds later holding a vacuum in one hand and a laundry basket in another. Jeff stood as she shoved the laundry basket in his direction.
“Help me?” She asked, doe eyes and all.
Jeff rolled his eyes and smiled, taking the laundry basket. “Of course.”
Annie plugged in the vacuum and turned it on while Jeff began picking up clothes. While she pushes the vacuum back and forth, she began to dance. Shaking her hips side to side, she flailed her free arm over her head, then turned back to smirk at Jeff. He smiled back at her as she went back to her dance.
He whispered then, only loud enough for him to hear, “I love you.”
She didn’t hear him over the vacuum, but he still said it. It was out there and he didn’t really know what to do with it.
The second time he said it, Jeff felt like he was in another world. He was in his own little bubble: he was letting Annie know that he loved her without her hearing it. It was keeping him safe from possible rejection, keeping him hiding in plain sight.
He said it next when she was half asleep. It had been a long day of work for the both of them, so even though it was a Friday night, they decided to stay in and watch Netflix. Annie was snuggled up against him, her cheek pressed against his chest. Jeff let her pick the movie and they ended up watching Love Actually, one of her all time favorites. He didn’t tell her that it was one of his too.
As they reached the end of the movie and the credits began to roll, Annie’s eyes fluttered closed. Jeff chuckled and pressed a soft kiss on top of her head.
“Annie,” He said, and only got a mumble in response. “Movie’s over.”
“Mmm,” She grumbled and turned closer into his chest.
He wrapped his arms closer around her as she tucks her head under his chin. He dropped another kiss on her he'd and whispered into her hair, “I love you.”
Annie mumbled something incoherent and Jeff chuckled. “Come on, let’s go to bed.”
The third time he said it, he almost got caught. Britta dragged the group out, mostly against their will, to a “Natalie is Freezing” concert happening at a bar near Greendale. Duncan was at a psychology conference and Britta had no one else to go with, so she guilt-tripped everyone else into coming with her. She only had lie to Shirley, who believed that they were going to a Christian Rock concert.
Needless to say, she was very disappointed when they pulled into the bar parking lot.
Pierce bought a round for everyone except Shirley, and they settled into a table in the back corner. Britta sat in the front, sporting her ”Natalie is Freezing” tour t-shirt. Abed was pressed against the wall with Troy on his other side, and Pierce sat next to Shirley, which she wasn’t too happy about.
Annie and Jeff were sat in the back corner of the booth, close together with their shoulders touching. The study group kept stealing obvious glances in their direction; they still weren’t completely used to them dating yet.
However, once the music started, everyone’s eyes were fixed on the stage. Jeff never understood Britta’s obsession with “Natalie is Freezing”, and he probably never will. But he was very content sitting next to Annie and spending the night with his friends.
The music was loud, echoing off every wall and drowning out all conversation. Surprisingly, everyone was getting into it, including Shirley. Annie was humming along and swaying slightly in her seat. She caught him staring at her and smiled, then rested her head on his shoulder. Jeff pressed a soft kiss on her head and whispered into her hair, “I love you”.
Abruptly, Annie pulled away with her eyes crinkled in a concerned way. Jeff felt his heart stop in his chest.
“What did you say?” Annie said, just loud enough for him to hear over the music.
Jeff swallowed hard and did what he did best: bullshitting. “Um, I said ‘do you want me to refill you?’” He said, pointing at her empty bottle.
Annie opened her mouth, then closed it and nodded. “Sure,” She said with a smile, although it didn’t reach her eyes.
Jeff’s heart didn’t stop racing until he was a safe distance away from Annie and the group. I’m going to get caught.
The fourth time he says it, it’s definitely the scariest. Jeff is sprawled out on the bed, setting up a lesson plan for his next class. If someone told me I’d be here a year ago, I would have laughed in their face, he thinks. Annie is in the bathroom getting ready to go have lunch with Shirley and Britta, and when she comes out, she leans over and gives Jeff a quick kiss.
“I’ll see you later?” She says, grabbing her purse off the nightstand.
“See you,” He smiles, watching her leave. Once she’s out of the room a safe amount of time, he adds, “I love you.”
He hears the front door close and he goes back to his work. No less than two minutes later, the door whips open loudly and Annie is yelling, “Jeffery Winger, we need to talk.”
Annie Edison is good at many things, but going with the flow is not one of them. She has to plan things out weeks in advance, often working out how she will react to certain things and predicting what emotions she will feel. When things don’t go to plan, she gets anxious. So when Jeff whispered “I love you” into her hair, she didn’t know how to react.
“What did you say?” She heard herself say, not fully comprehending the words coming out of her mouth. She could see Jeff swallow, every motion of his throat amplified. She could practically hear his thoughts rattling around his brain.
So when he said, “Um, I said ‘do you want me to refill you?’”, she felt her heart sink. She heard him, she knew she did. All she could do was open her mouth, close it, then nod. She watched Jeff walk away, a frown growing on her face.
Why did he lie? And more importantly, was this the first time he said those words?
She tried to think back, trying to discover if there was something she had missed. There was that one time when she was half asleep, but she chalked it up to a dream. Maybe it wasn’t a dream after all…
Jeff came back, drink in hand, and sat down next to her. She didn’t know what else to do except rest her head lightly on his shoulder again. While she acted like everything was fine, her mind didn’t stop racing for the rest of the night.
It has been two weeks since then and Annie still couldn’t stop thinking about it. After getting ready for a lunch date with Britta and Shirley, she walks out into the bedroom. Jeff is typing something on his laptop but looks up when she waltzes into the room. I’ll never get over the fact that he looks at me like that, she thinks as she bends over to give him a quick kiss.
“I’ll see you later?” She says, grabbing the purse off the side table.
“See you,” He says, smile on his face.
She leaves the room, digging through her bag and looking for her phone. When she doesn’t find it, she remembers that she left it perched on the side of the sink.
“Damn,” She says, walking back toward the bedroom.
That’s when she hears him, saying those three words again only to the four walls of the room. “I love you.”
She turns around immediately and escapes out the front door. Deciding not to wait for the elevator, she runs down the stairs and ends up in the small lobby. She paces back and forth, mulling the situation over in her head.
Why won’t he say it to me? Is he scared? Is he unsure? What should I do?
After some deliberation, Annie makes a final decision: she was going to do something. Back up the stairs she goes, determination in her eyes.
Before she could back out, she barges back into the apartment. “Jeffery Winger,” She says, “We need to talk.”
Jeff steps out of the room a few seconds later, looking sheepish with his hands in his pockets. “What’s up? I thought you left,” He says, looking very confused.
She crosses her arms. “Why won’t you say it in front of me?” She says, trying to keep her voice steady.
Jeff opens his mouth, closes it, then opens it again. “I don’t know what you mean.”
“Come on, Jeff. You know exactly what I’m talking about. Is it because you don’t mean it? Are you not sure about us anymore? Because if that’s it, I’d like to know sooner rather than later,” Annie is dangerously close to breaking down into tears. Ever since she heard him say it, she has been working it up into a big deal in her head.
“Woah, of course not,” Jeff says, crossing the room and carefully placing his hands on either side of her jaw. “I’m just…”
When he doesn’t say anything for a few seconds, Annie whispers softly while avoiding his eyes. “You’re just what?”
He exhales quickly and Annie thinks it’s the end. He’s going to break up with me. This is it.
“Annie, I’m scared.”
She really hadn’t been expecting that, so she finally meets his eyes. “About what?”
He drops his hands to her shoulders and gives them a squeeze. “I’ve only said those words to a few people in my life, most of them family members. It means a lot to me, and… I want to make sure you feel the same way before I finally say it. I don’t want to make you uncomfortable,” He says, his voice shaking slightly.
Annie laughs, she can’t help it. He seems taken aback by it and almost steps away from her, but she grabs his wrists. “The fact that you haven’t figured out that I’ve been in love with you since our first year at Greendale is incredible.”
Jeff’s eyes widen in shock and for a second, Annie is afraid that he’ll close himself off from her. But then, he’s leaning down and kissing her hard.
Annie gasps and sinks into the kiss, pulling him closer. If Freshman Annie could see her now, she wouldn’t believe her eyes.
After a few minutes, Jeff pulls away and looks into her eyes. He looks absolutely blown away and it gives Annie the same butterflies she got whenever he looked in her direction during study group. This is what she’s always wanted. “I love you, Annie.”
She smiles back up at him.”I love you too. Of course I do.”
As it turns out, the fifth time he says it, it is all worth it.