I in no way own Community. I'm just a huge fan.
As Jeff drove from the airport to the hotel he wondered why he had agreed to do this. He knew Annie could convince him to do things he'd never normally do, but talking him into going to an out of town wedding was beyond impressive. He doubted his mother would even be able to do that.
As he drove he mentally replayed the phone conversation from two days ago.
Jeff: You want me to go with you to a wedding? In Chicago?
Annie: It's just for the weekend. And it won't cost you much. The bride's paying for travel expenses and the hotel rooms for everyone. And I already had a plus one so you'd be covered. It will be like a free vacation. It should be fun.
Jeff: The tone in your voice suggests otherwise.
Annie: Please Jeff. I really don't want to go by myself. Britta was suppose to go with me but-
Jeff: You convinced Britta to go? How drunk was she when she agreed to that?
Annie: I told her some people from Greenpeace would be there and that she and I could make fun of the institute of marriage.
Jeff: Let me guess, none of that was true.
Annie: Well….
Jeff: You're good. Wait, isn't Britta still in South America for the summer?
Annie: Hence the problem. She promised she'd be in Chicago by Friday morning for the wedding. I told her she should get back sooner, but no, she kept saying she wanted to stay as long as possible to get the 'whole experience'. Then a hurricane came and destroyed the airport and now she's not sure she can even get back for the beginning of classes, much less for Friday's wedding.
Jeff: Typical.
Annie: So Britta's not available. Troy and Abed have tickets for a sci-fi convention this weekend. Both Andre and Ben are sick so Shirley has to take care of them. And Pierce…..I've only talked to him once since paintball and that didn't go well so I can't ask him.
Jeff: I'm actually offended. You would ask Pierce to go with you before me?
Annie: Don't let it go to your head, but yes I would ask you to go before Pierce. I'm just letting you know that if you say no I have no one else to ask.
Jeff: If it's such a hassle why are you even going anyway?
Annie: The bride's from my rehab group. She said it's very important that everyone from our group be there for her special day. It means a lot to her. She'll never forgive me if I don't go.
Jeff: First of all, speaking as someone who's known a lot of divorce lawyers, I doubt this will be her only 'special day'. And second, you said you never speak to anyone from rehab. And now you're scrambling to see everyone at a wedding?
Annie: Jeff, I'm asking you as a friend to please go with me to this wedding.
Jeff: Wow, I can actually see your formidable face over the phone.
Annie: If you do this for me I'll help you with all your homework for next year.
Jeff: You already do that.
Annie: Jeff-
Jeff: Ok, I'll go.
Annie: You will! Thankyou, thankyou, thankyou!
Jeff: But you definitely owe me for this.
Annie: Oh. Ok. What did you have in mind?
Jeff: I'm not sure yet, I'll have to think about it. It'll definitely be humiliating, but I promise it won't be cruel.
Annie: Ok. Wait, it's not going to have to do with living in the moment, is it?
Jeff: I'll see you at the wedding.
Although he'd never admit it out loud, a part of him was actually looking forward to this. Not the wedding specifically, but spending some time with Annie. Unlike last summer he saw more of the study group during this summer. He had hung out a lot with Abed and Troy and even had dinner at Shirley's a few times. And just before she left he and Britta had had a memorable night at a karaoke bar which ended with the two of them drunkenly singing 'Piano Man' at the top of their lungs. But he had only seen Annie a couple of times. Not because he was avoiding her. It was just that with her summer job no one from the group had seen a lot of her. So being able to see her for a few days was something he could look forward to.
Though that was before she had called him yesterday to give him a detailed travel itinerary and hotel details and he found out that they would be sharing a room. It's no big deal, she had said. The room has two beds so there shouldn't be a problem. But the idea of sharing a bedroom with Annie for two nights made him more nervous than he thought it would. Seeing her was one thing, but sleeping in the same bedroom as her was something else entirely.
That information had caused him to remember a brief conversation Abed had had with him the day the two of them and Troy went to see the new Transformers movie. It was after the movie when they went to have lunch at a diner. Troy had gone to try his luck at the claw machine when out of the blue Abed said "Annie wasn't really kissing me."
Jeff looked up from his phone in shock at the change in topic. "What".
"In the library during the paintball game. When we kissed Annie wasn't really kissing me, she was kissing Han Solo. So you shouldn't be jealous of me."
"Why would I be jealous?"
"You were jealous of Rich. I just didn't want you to be jealous of me."
That was the only time they had talked about what happened between Abed and Annie during paintball (even though Abed did most of the talking.) But Jeff seemed to guess what Abed was saying; he wasn't into Annie like that so Jeff shouldn't be worried about it.
Hearing Abed say that seemed to bring up everything he felt about Annie, and how unresolved the whole situation was. That conversation, along with the sleeping arrangements, almost had him cancel this whole trip. But he knew she would never forgive him if he canceled now. So he just told himself he had to suck it up, go anyway, and find a hot single bridesmaid who had her own room.
As he pulled into the hotel parking lot he checked his watch. Originally he was supposed to fly with Annie and get in at 1:30. But his alarm clock failed to go off and he missed his flight, causing him to take the next one two hours later. He must have left a dozen messages on Annie's phone assuring her that he would be there (he knew she had to be freaking out). As he walked into the hotel and up to the front desk he quickly texted her that he was in the lobby and would be up in a few minutes.
"Hello, I'm here to check in."
The hotel clerk kept looking at the computer screen, clearly bored by his job. "Name?"
"Jeff Winger. "
"Winger, Winger." He looked up and he face lit up in sudden understanding. "OH, of course. You're here for the Statia/ Johnson wedding. I'm sorry, I should have known. A young woman named Annie Edison checked in earlier and specifically said a man named Jeff Winger would be here to check into the same room as her. She even left me a picture so I would immediately know who you were. Your girlfriend is very nice, even if she's a bit high strung."
"Oh no, we're not-"
"There you go, you're all checked in. Here's your room key, along with the photo Miss Edison left. You two make a lovely couple. Have a nice stay."
Jeff silently took the photo and looked at it. It was from Abed's birthday. He and Annie were outside the restaurant still in their Pulp Fiction costumes, but Annie had removed her wig and her hair was sticking out all over the place. He didn't tell her at the time, but he thought it made her look cute. As he looked at the photo he wondered if she had brought it to give to the hotel clerk, or if she always carried a picture of the two of them around.
He took the elevator to the fifth floor and went over to their room. He didn't want to accidently walk in on her if she wasn't decent, so he loudly knocked on the door. "Annie, its Jeff."
The door opened and there stood Annie. She had a bathrobe tightly tied around her and her hair was up in a towel turban. "Jeff! You're here." He barely had time to brace himself before she wrapped her arms around him in a tight hug. "Thank you again for doing this." She held him for a few moments before separating and dragging him into the room. "Come on, you have to get ready. Get your suit and shower stuff and get going."
"Annie, I just got here. Give me a minute before-"
"Jeff, The wedding starts at six, and it's going to take you at least an hour to get ready. I'm sure your hair alone will take a good chunk of that time."
"As I've said before." Jeff said as he pointed to his hair. "This masterpiece takes work."
"Well then get going." She said as she shoved him towards the bathroom.
"Ok, just let me get my stuff." Jeff got his suit and toiletry bag, which rivaled Shirley's purse in size, and headed into the bathroom.
An hour later he emerged all ready. He was wearing his Pulp Fiction suit, except this time he had on a red dress shirt instead of a white one. "I'm ready. So stop worrying about-"
He stopped talking and just stood there when he saw Annie. She was wearing a strapless royal blue cocktail dress. It was short enough to show off her legs, but in no way did it make her look trashy. Her hair was pinned up and she had on black high heeled shoes with straps that went around her ankles. She looked sexy and sophisticated and in every way a woman.
Annie turned around from the mirror, blushing when he kept staring at her. "What? Is there something wrong?"
"No. Nothing's wrong. I've just never- you look great."
"Thanks. So do you."
They stood there for a few moments, taking in each other's appearance, when she suddenly gasped. "Oh, I have something for you. Close your eyes."
Jeff closed his eyes, and a few moments later felt something square and medal thrust into his hands. "Ok, open them." When he opened his eyes he saw that he was holding a silver flask with a purple bow tied around it.
"Um, thank you. What's this for?"
"So you can have a good time. There's no alcohol being served no one who can't drink is tempted. And I knew this would be hard enough for you so I found a way for you to still have a few drinks so you could enjoy yourself. There's a liquor store on the way to the church, you can stop there and fill up."
Jeff looked at the flask, clearly touched by her thoughtfulness. "Thanks."
"Just promise me that you won't let anyone else drink, that you be discrete about it, that you leave any liquor bottles you buy in the car, and that you don't get too drunk."
Jeff smirked as he removed the bow. "I didn't know my present had so many rules attached to it."
"I'm serious Jeff."
"Annie, I promise I will follow each of your rules to the letter. And, this means a lot to me. Not so much that I can drink, although that's a big plus. But that you would go so out of your way for me."
He walked over and held out his arm. "Ready, Milady?
She smiled as she linked her arm with hers. "I am, Milord."
