By his third year at Greendale Jeff hung out with his Study Group actually no his friends more outside of Greendale. He bonded with them individually as they had surprisingly similar interests and hobbies they could do together. He was also seeing his former work colleagues less and less only seeing Ted for the occasional consulting job.
With Troy and Abed, Jeff would head over to Casa de Trobed or they would over to his apartment and they would play video games together. They mostly played Call of Duty or Need for Speed.
With Shirley ever since their encounter with The Germans and their shared history of Foosball they had grown surprisingly close having bi-weekly dinners.
With Britta they would go to L Street and NOT the Red Door. They had been doing this since their second year and Ian Duncan would occasionally join them all though he seems to be strangely missing this year.
With Pierce ever since their Dungeons and Dragons game Jeff was surprised by how much he enjoyed it although he was a little ashamed of doing so. Him and Pierce would meet up with Neil and sometimes with few others and play. While they were enjoyable Jeff still felt guilty for coining the term "Fat Neil" and so he played this to make sure Neil was alright.
Finally with Annie they watched Disney movies together. Annie found out about Jeff' love for Disney movies after they all abandoned the Dean for his documentary. She went over to Jeff's to see if he was ok when she saw he was watching Mulan. Jeff had obviously tried to deny he was watching and was flicking through channels but once Annie pointed out to the DVD on the coffee table and Disney eyed him he fell through and admitted his love for Disney movies.
Jeff had started watching them at a young age whenever his parents started arguing he would get out a VHS tape and watch one to take his mind away and get sucked into a magical place.
Jeff had offered Annie to stay and watch the rest of Mulan and made her promise not to utter a word of his love of Disney. She laughed of course but knew Jeff was very sensitive about his image and that he didn't like to reveal his personal secrets to his friends.
Jeff had enjoyed Annie's company and said they should make this a weekly thing, she instantly agreed and made a schedule that they should meet up every Thursday and said that she should choose the next film then Jeff the week afterwards.
They continued this enjoying each others company, eating pizza, making fun of characters and some plot lines. Jeff would sometimes pick an older live action movie such as Herbie since Annie had never seem them, which Annie enjoyed since she was learning of Disney's rich history.
It was after Jeff's recent Seacrest Hulk rage outburst that Jeff was worried that Annie wasn't going to turn up, he figured that she's probably freaked and never wanted to be alone with him. However as always Annie surprised him smiling as always as she stood in his doorway with a box of pizza. She didn't judge him, she didn't mock him, she just came to continue their get-together. She had brought over Aladdin as she knew it was Jeff's favourite.
Midway through the film Jeff had turned to Annie who was snuggling next to him and said thank you for coming over. He needed this a relaxing evening with a person he loved, wait what? Jeff loved all of his friends maybe even Pierce but there was something different Annie. So with that his mind raced about kissing Annie, was she too young she was 21 now, was he too much of an jerk according to Abed he's had a lot of character growth and development. So screw it he's going to be selfish for the right reasons he wants this and he's sure Annie wants it. He lifts her chin with his fingers and gives her the most passionate sweetest kiss he's ever given. She kisses him back and they stop a couple of minutes later as they realise that the song being played is "A Whole New World" to Jeff and Annie this certainly was.