Jeff groaned as he opened his stinging eyes. While he was hung over, he wasn't in nearly as bad of shape as he expected to be. As he looked down and saw that he had slept in his suit he thought back to what happened after he started drinking like it was his job. He remembered dancing like an idiot and at one point telling one of the groomsmen that he looked like James Bond if he was from Milwaukee (he wasn't sure what that meant.) Once the reception ended he and Annie came back to their room, and then-.

"Morning."

Jeff sat up as Annie approached him. Her hair was up in a ponytail and she had on sweatpants and a Greendale t-shirt. He was amazed she could look this good first thing in the morning. He tried to keep his face blank as the memory of kissing her (again) fully formed in his head.

"Hey. How'd you sleep?"

"Pretty good. I just got up a few minutes ago. What about you?"

"I slept fine."

Annie nodded as she sat down on the end of Jeff's bed. She took a deep breath as Jeff absentmindedly tried to comb his hair with his fingers. "Jeff, I've done a lot of thinking about what happened last night. And, before you say or do anything there's two things I have to ask you. And I need you to answer them. Ok?"

Jeff simply nodded as he looked into her eyes. "All right."

"Ok, the first thing. Us kissing last night. Was that? I mean, I know you had a lot to drink. And when you're drunk you do things you wouldn't normally do. What I need to know is, was that….I mean, if you weren't drunk. What I'm trying to say is, was that the only reason you…..?"

Jeff knew what she was asking. Was kissing her just a result of being drunk, or did it mean something more. He knew he could easily lie and say it was just him being drunk and wanting to kiss any girl, or that he didn't even remember it happening. But he knew he owed her the truth, even if it was sure to further complicate things between then. "Annie, I don't need to be drunk to want to kiss you."

Her face lit up for the briefest of moments before the smile left her face. She looked back at him with such seriousness it made her normal formidable face seem almost comical. "Ok, now the second thing. And please don't say anything until I'm finished. I've thought about this a lot and I know how this is going to sound, but you have to make a decision, regarding us, right now. Because I can't do this anymore. The false starts and condescending actions. You kiss me and then want to act like it never happened. You refuse to be with me, but freak out when I want to date other guys. Every time I think I'm over you you open that door again, and I die a little bit when you slam it shut. I need to know once and for all if you want to be with me or not. And I need to make it very clear that this is it. What I mean is, if you say you don't want to be with me then there is no second chance. If next month or so you become jealous if I'm with someone else or say that you like me and are ready to be with me it won't matter. I won't let you open that door again if you decide to close it this time. I'm not trying to influence your decision, but you need to understand what I'm saying if that's what you choose."

Annie stood up, running her sweaty palms over her pant legs. "Ok, I'm going to go have breakfast in the lobby and then say goodbye to Jill and Tom before they leave for their honeymoon. I'll be back here in about two hours." And with that she quickly left the room before he could say anything to her.

Jeff sat further up in bed, staring at the wall in shock. He realized what she really meant by saying when she would be back. It meant that was when she was expecting his answer. He essentially had two hours to tell her his decision.

He felt himself growing angry as he thought about it. Jeff Winger didn't do ultimatums. He didn't jump when someone said you have to do this or else. And who was Annie to demand anything from him. It's not like she's so great. She was annoying and high strung. She was childish and was always making him do things be would never do. Like go out of his way for others. And make him want to be a better person because she expected the best in others. Annie was kind, and sweet, and was definitely his equal. He was always on his toes when he was around her. She was attractive and made him laugh and- damn it.

Who was Jeff kidding? He was crazy about her. And as much as he hated to admit it she was right. Whether he always meant to or not he had toyed with her heart way to many times. It was time once and for all to make a decision. Could he be in a relationship with Annie Edison or not.

And that was one thing he knew to be true. A relationship. While she was incredibly hot and he would definitely like to sleep with her, he didn't want her to just be another notch on his figurative bedpost. If he was going to be with her it wouldn't just be for a quickie in a broom closet. It would be a full on relationship. Maybe that's what scared him about this whole thing.

He definitely liked her. She amused him and made him feel things he didn't think he was capable of feeling. She could make him both happy and nervous with just a simple look. If there was a one, and he never thought about one's when it came to women, she was as close as you can get.

So why was he not with her?

There were two big reasons for that; the group and her age. And now Jeff had to work out if he could get past those obstacles.

First he figured he'd deal with the problem of the group. Because while he rarely admitted it, he deeply cared about them and had to consider their feelings on this issue. Abed wouldn't care. If anything he'd see it as a plot point in the 'television show' he saw their lives as. Troy might object at first, only for fear of what dating within the group might do to all of them. But if he accepted him and Britta hooking up he'd support him dating Annie. Pierce (even though he left the group Jeff couldn't help including his reaction in all this) would simply make a few sex jokes and then go back to calling Jeff gay.

Shirley would be a harder sell. She was sure to condemn him for being in a relationship with a much younger woman and would feel he would corrupt and hurt Annie. But he was sure he could get her to come around. If it came to it he could always point out that people objected to her getting back with Andre and that worked out when she followed her heart.

Britta would be the one who would take it the hardest. Even though they were pretty much done with all that (they decided they shouldn't sleep together anymore that night they went to the karaoke bar) she would still be mad that another guy chose Annie over her. She was sure to call him a jerk and try to guilt Annie with some talk about friends not going after men the other was involved with. But he knew he could break through to her. It wouldn't be easy, but he knew Britta well enough to get her to see that this was a good thing.

So the first obstacle was thought out and dealt with. Now came the second one, the age thing. Could they put their age difference between them? To her it wasn't a concern (it never had been). But he knew people would whisper that she was a gold digger or he was either her father or a dirty old man. Could he handle others judging him when he held her hand or kissed her in public? Could he truly feel right about having a woman so young in his arms?

Jeff sighed deeply and thought about it. When it came down to it what others thought didn't affect him as much as it once did (two years at Greendale had definitely toughened him up to dealing with other people's ridicule.) And he knew it didn't affect Annie. So the final question was, did it affect him?

He thought back to other women younger than him that he had been with. Pierce's step daughter hadn't been that much older than Annie. When you really thought about it Vaughn and especially Rich weren't much younger than him. And Annie wasn't as innocent as she had been when they first met. She was living above a 'marital aid store' (he loved that that was what she called a sex shop). And he couldn't forget how vivid her dungeon & dragons sex pantomime was if he tried. She was supporting herself and was living on her own. While she still had that youthful spark of naivety, she wasn't exactly a kid anymore.

Jeff thought about the things in his life he truly regretted. And he realized that this, not being with Annie, would be something he would always regret. Because she had meant what she said. If he said no this time there wouldn't be a second chance. Even if it didn't work out he would always hate himself if he let her slip away because of fear.

Quickly throwing on his shoes Jeff grabbed a room key and left the room, taking the stairs to the lobby. When he got there he saw Annie standing next to the front doors. She had a suitcase in her hands as she walked out of the hotel.

"Annie, wait." Jeff yelled as he ran out of the hotel. Annie turned around in surprise as she handed the suitcase to Tom. Jeff stood there cursing himself for his stupidity. She wasn't leaving; she was just helping the bride and groom pack their stuff in their car.

He stood to the side as he watched her hug the couple and wish them a happy honeymoon. Once they drove away she walked over to Jeff. "I didn't expect to see you down here."

"Annie, after what you told me I've done a lot of thinking. And I have to say something to you. There are a million reasons why we shouldn't be together. Our age difference, the group, your ability to drive me crazy."

Annie's eyes started to tear as emotional pain flowed through her. But before she could say anything Jeff cupped her face in his hands and kissed her deeply. As he pulled away she looked into his eyes and almost had a heart attack from the shift in emotion her heart just felt. "Wait, are you-?

"I'm saying that none of that matters. You are one of the kindest, most wonderful women I have ever met. And if I let you go I would hate myself forever. I'm saying I'm ready to give this a chance. Annie, I can't promise you how this will end. But I'm finally ready for this to begin. "

She let out a squeal of delight as she kissed him back, practically melting from the feel of his lips. They stood there in the entranceway kissing and holding each other until she finally pulled away from him.

"I bet you say that to all the girls." She said with a grin.

Jeff smiled back. "For once Annie Edison, you are completely wrong."