The burgeoning feelings between the two are sub-plots to multiple second season episodes, and by the third season it is fairly clear the show is moving in that direction. During a party to celebrate Abed and Troy moving in together, Jeff creates several different timelines when he rolls a dice in order to get out of getting the pizza.
Most of the timelines show them kissing or getting intimate., Jeff looks into his heart and finds several images of Annie which can hint toward the depth of his feelings for Annie.
Because when there is a disconnect between the way that characters are written and the way that they are either acted or perceived, THAT is when things like our affectionately named “Bobrowgate” occur.
See, it doesn’t matter in this scenario if Andy Bobrow is right or if Jeff/Annie shippers are right.
Jeff aggressively pursued Britta romantically in Season One, but she repeatedly refused him; he did see some hope with her after Shirley reveals that Britta had a sex dream about him.
Jeff repeatedly denied his attraction to Annie who was frustrated by his reticence but understood how uncomfortable he was with the age difference.During her tap dance recital, Britta saw that Jeff and Slater were actually serious, which made her realize her own potential feelings for him.Jeff and Annie had a close but complicated dynamic during their six years together at Greendale.As the ladies of Hot Switch and I explained in a recent episode (and I believe it was Jaime who made this observation), there are moments that cause dysfunction and dismay within a fandom.These moments occur when the image that the fandom has created in their minds of a particular character, including their wants, desires, dislikes, likes, etc.