23 months later

"Oh, it says here that every fifteen minutes the faces protected on Crown Fountain spit water at people. And that when it was being built there was controversy that its size would cause other parks to build competing structures so-"

Jeff good naturally rolled his eyes as he pulled Annie into a one armed hug. "Annie, if you keep your head in a book reading about the sights you won't be able to see then." He said as he kissed her.

"I just think it's interesting to know more about what we're seeing. It makes you appreciate it more."

Jeff lightly bopped her on her nose. "I think we both know what I appreciate."

Annie laughed at his comment. "When did you become so lame Mr. Winger?"

"I don't know. Maybe it was when I gave you a key with a big purple bow tied to it. Or that time I didn't play laser tag with Troy, Abed and Britta because I had to get you cold medicine when you had the flu."

"I thought you said you loved it that they came with you and Troy and Abed starting doing a radio production of Star Wars on the PA system?"

"Yea, we had fun. But it was still lame that we had to cancel."

Annie chuckled and looked over as they walked by the cloud gate structure, nicknamed The Bean. They walked over and asked another tourist to take a picture of them by it. Once he gave them their camera back they looked back at the picture, showing the two of them beaming with happiness.

It had been almost two years since they started going out, and Jeff did not regret his decision at all. Once they got back to Greendale they told the group that they were now a couple. His predictions of their reactions had been fairly accurate. While he knew it wouldn't bother Abed Jeff hadn't expected that he would be their biggest supporter. Abed had brought up that "many times the two people on sitcoms no one expects to be involved romantically end up having the strongest relationship. Like Chandler and Monica on Friends." Troy had been surprised, but didn't think it was that big of a deal. Pierce (who ended up rejoining the group during the Dean's memorable attempt to bring Spain's "running of the bulls" to Greendale) had a bit of an unexpected reaction. While he made a few jokes that Jeff was just using Annie to cover up his gayness he privately pulled Jeff aside and said that he would make Jeff sorry if he ever hurt Annie.

At first Shirley poured the mother guilt on the two of them. She felt Annie was too young for Jeff and that he was just using her for "acts the bible doesn't condone." But Annie had fiercely stood up for them, saying that she wasn't a kid and that she and Jeff were extremely happy together. Perhaps it was her passion that did it because afterwards Shirley quieted down on the issue and eventually accepted them.

As predicted Britta did take the news the hardest, and was the one who took more than a day to come to terms with it. That had been a hard week. But the two of them separately had a long conversation with her about it. And she finally was happy for the two of them. When they eventually said "I love you" for the first time in front of the group she had the loudest "OH!" of everyone. Then they all groaned when she followed up with telling them that saying I Love You too often desensitizes the meaning of the phrase and turns it into just a robotic phrase couples feel they automatically have to say to each other.

It seemed Jeff was constantly finding out more reasons to love Annie. Like discovering that she occasionally talked in her sleep about back to school sales no matter what time of year it was. Or when they moved in together and he found out she had a stuffed dog named Mr. Barky Bark.

Their relationship was far from picture perfect. They argued and fought, particularly when they first started going out. One really bad fight had him spending the day with Troy, Abed and Pierce and her with Shirley and Britta to try and calm down before they apologized and made up that night. But he wouldn't change a thing about them. In some ways he was actually glad for those early fierce fights. It had proved to them that they could survive anything.

Annie smiled as she looked up at the Chicago skyline. "I love it here."

Jeff nodded in agreement. After graduation they talked about taking a vacation somewhere. And it seemed only natural that they go back to the city they started their whole relationship in. Though what Annie didn't know was that Jeff had another reason for wanting to come back here.

Making sure Annie wasn't looking he checked his pocket to make sure the ring box was still safely there. He had bought it just before they left and had been waiting for just the right place to propose. Though when he woke up today he realized he knew the perfect place.

"Come on, this way."

"But Jeff, the restaurant's in the other direction."

"There's something I want to show you first."

They started walking down Columbus Drive, in the direction of the hotel they stayed at two years ago was. It seemed only fitting that the outside lobby be the place Jeff would propose to Annie. After all, that was where they had begun this wonderful journey together.