Word Count: 1,730
Characters/Pairings: Jeff, Annie, Britta, Abed, Troy, Pierce, Annie/Jeff
Warning: Mention of miscarriage.
Disclaimer: I don't own Community and never will. No copyright infringement intended.
Summary: When they first started sleeping together, Jeff had never expected to fall in love with Annie.
When Jeff and Annie first started sleeping together, they agreed that it was a casual thing. Jeff made sure to remind her they weren’t in a relationship and never would be in a relationship.
“I know we’re not in a relationship. Jeff, it’s okay that we’re not. I’m fine with it,” Annie assured him after Jeff said it to her for what seemed like the millionth time.
“I think he’s protesting way too much,” Abed whispered to Troy. He had seen this in so many movies. It was a common plot.
“Me too,” Troy agreed. He and Abed watched as Jeff and Annie flirted back and forth before the entire group arrived.
Five months after they started sleeping together, Jeff met Annie’s parents. Aaron and Polly Edison wanted to meet their daughter’s friends. Annie didn’t tell them she and Jeff were more than friends, which was for the best.
“Mr. and Mrs. Edison are going to find out about Annie and Jeff. This is the way these things go.” Abed suspected Jeff and Annie wouldn’t be able to keep this a secret anyway. It was obvious something was going on between them.
“Of course they’re going to find out, Abed. It’s not good to keep these types of things secret,” Shirley scolded. She smiled at Jeff getting along with Aaron and Polly, however.
Sure enough, Aaron and Polly learned of Jeff and Annie’s non relationship before they went home. Polly was thrilled that her daughter had found someone, and Aaron took Jeff aside to talk to him.
“Don’t hurt my daughter or you’ll have to deal with me. I’ll come back here and find you and do some damage,” Aaron threatened.
“O…kay. I won’t hurt her.” Jeff definitely didn’t want to hurt Annie now. He was terrified of her father, and had no doubts that he would act on his threat.
Jeff was shocked when he realized he was in love with Annie about eight months after they started sleeping together. The group had met up as usual when the truth hit him.
“Watch Jeff. In the next five minutes, he’s going to realize he’s in love with Annie and freak out. He’ll push her away, Annie will end their relationship, Jeff will get her back by admitting his feelings for her, and then they’ll be extremely happy.” Abed had seen this plot in a ton of romantic comedies.
Troy, Abed, Shirley, and reluctantly, Pierce kept their eyes on Jeff as the realization slowly hit him when he was laughing at a joke Annie told.
As predicted, Jeff freaked out. Falling in love with Annie hadn’t been part of his plan. It was supposed to be a casual thing!
“I can’t be in love with her. This wasn’t supposed to happen,” Jeff ranted to Britta a few days later. He didn’t want to talk to Pierce, Troy, or Abed about this.
Britta sighed. “I felt the same way about you,” she reminded him. She had eventually moved on from Jeff, but it had taken a long time.
“Good point. I’m just going to go talk to Shirley. Sorry,” he apologized before bolting over to the seat next to Shirley. Britta was one of Jeff’s best friends, but she had been in love with him and talking to her probably wasn’t a great idea.
“Follow your heart, marry her, and make a lot of babies with her,” Shirley advised after she and Jeff talked for a little while.
“What kind of crap is that?” Jeff questioned. He had just found out he was in love with Annie! He wasn’t ready to even think about marriage or kids yet! Whoa, yet? Where had that come from?
“Jeffrey!” Shirley shooed him away and Jeff returned to his seat to silently freak out about being in love with Annie.
Sure enough, just like Abed predicted, Jeff started pushing Annie away and she ended their “relationship”. This lasted for three weeks before Jeff broke and confessed his feelings for her.
“Jeff, I love you too.” Annie smiled at him, and she and Jeff kissed. They pulled apart when the group began protesting about the public displays of affection.
Fourteen months after they officially started dating and confessed their feelings for each other, Jeff and Annie moved in with each other.
Three months after that, Jeff decided to propose. He reluctantly took Troy, Abed, and Pierce along to the jewelry store for advice on what engagement ring to buy.
“You need one that says you love her, but is also expensive and said you put a lot of money into this,” Pierce advised.
“Okay, not listening to Pierce.” Jeff just wanted to find a ring he hoped Annie liked. He wanted her to say yes.
“This is really pretty,” Troy told Jeff about one ring when he was down to three of them.
“This one is beautiful. Annie will love it,” Jeff said of a ring that Abed had in his hand. It was simple and elegant. It was a lot of money, but not as expensive as the other two rings.
“Good job.” That came from Pierce, who wasn’t really interested at all in what was going on.
Two days later, Jeff decided to take Annie out to eat at their favorite restaurant. He planned on proposing to her at home, in case she rejected him. He didn’t want an audience for his humiliation if Annie said no.
“Of course I’ll marry you!” Annie squealed later that night. She wondered why Jeff had planned a perfect for them. They usually didn’t go all out for date nights.
Jeff smiled at her and then slid the engagement ring on her finger. “I love you,” he whispered in her ear. He couldn’t believe Annie had agreed to be his wife!
“I love you too, Jeff!” Annie couldn’t wait for Jeff to be her husband. It was so surreal they were engaged now. She had a wedding to plan! Annie needed Britta and Shirley’s help. Her mom could help too, but Britta and Shirley could probably help her out more.
Ten months after Jeff’s proposal, it was time for Annie and Jeff to get married. They planned a small wedding. Britta was her maid-of-honor and Shirley was a bridesmaid. Troy, Abed, and Pierce were Jeff’s best men. He hadn’t been able to choose between Troy and Abed, and leaving Pierce out seemed too cruel.
“I can’t believe we’re married now, Mrs. Winger,” Jeff told his new wife at the reception when they started dancing for the first time.
“I can, Mr. Winger.” She was Annie Winger now! She couldn’t wait for her high school reunion to throw it in everybody’s face.
Jeff and Annie went to Hawaii on their honeymoon. Shirley, Pierce, Troy, Abed, and Britta pretended they didn’t follow them there. They avoided the newlyweds as much as they possibly could.
Six months after the wedding, Annie began throwing up in the mornings and suffered from nausea all morning. It was Britta who pointed out the possible cause to her.
“Jeff and I wanted to wait for kids! I can’t be pregnant!” Annie screeched to her friend. She was terrified of becoming a mother.
Britta winced. “I know you wanted to wait, but it may be too late for that. Take a pregnancy test.” She was excited about possibly becoming Aunt Britta to Jeff and Annie’s future baby.
Sure enough, the pregnancy test came out positive. Jeff and Annie’s life was about to changed forever. They couldn’t wait to be parents.
Eleven weeks into the pregnancy, Annie woke up to spotting and cramping. The doctor confirmed her and Jeff’s worst fears – She had miscarried.
The Wingers had been excited about their first child. The miscarriage devastated them, but luckily, the group was there for him. Shirley, Britta, Abed, Troy, and Pierce rallied around Jeff and Annie.
Annie and Jeff began trying for a baby again about six months after the miscarriage. They conceived two months later.
“This time is going to be different,” Jeff murmured to his wife.
“I feel it too,” Annie admitted. She was worried about miscarrying again, but had a good feeling about this pregnancy.
Seven months later, Jeff was by Annie’s side as she experienced a twenty-one hour labor with only one epidural. The first cry of their newborn was something Jeff would never forget. He later denied crying when the baby was handed to him.
“What are we going to name her?” Annie couldn’t think of a name for her daughter. She was coming up blank.
“Johanna Elizabeth Winger,” Jeff decided. It was the only name he kept going back to during the pregnancy.
“Johanna. How do you like that name, Baby Girl?” Annie smiled at her daughter. The baby let out a little noise and seemed to smile.
“Johanna Elizabeth it is.” Jeff took his daughter back off Annie and sat down in the chair to stare at her.
Fifteen months after Johanna’s birth, Jeff and Annie welcomed their second daughter – Tessa Lynn Winger. Johanna adored her little sister and nicknamed her Tess. It stuck.
Twenty-three months later, Jeff and Annie’s third daughter arrived. They named her Shiloh Christine Winger. Abed pointed out that it was the name of one of Brangelina’s kids, but neither cared. Jeff and Annie loved the name.
Jeff and Annie thought they were done having kids, but had a surprise in the form of a son named Matthew Jeffrey Winger three years later. Matthew was their final child. Johanna, Tess, and Shiloh spoiled their younger child.
On their twenty-fifth anniversary, Jeff and Annie celebrated with family and friends. They had all the important people in their lives with them. Nothing was better than that.
On their fiftieth anniversary, Jeff and Annie were surrounded by their friends, their kids, and grandchildren.
“I’m so glad I married you,” Jeff whispered to his wife.
“I’m glad I married you too,” Annie whispered back. She didn’t regret marrying and having a family with Jeff at all. He was it for her. Jeff was her soul mate.
“I’m glad we decided to start sleeping together all those years ago.” Jeff was happy he had fallen in love with her.
“Me too.” Annie pulled away from his arms and then turned around and kissed him.
Annie and Jeff had had a wonderful life together. They wouldn’t change a thing about their relationship.