Craig Pelton was an unusually passionate man, not to mention a man of unusual passions, and the thing he was most passionate about (and, some would say, his most unusual passion) was Greendale Community College. Greendale had changed his life; he had arrived there immediately after high school as an aimless, mostly friendless nerd, and had left two years later energized with purpose. He would become a community college educator. He would follow in the footsteps of Will Anderson, Greendale's dean, who had become his mentor and friend, who had guided and encouraged him, and taught him to believe in himself.
Two years later he was back at Greendale with a degree in English and Education and a job in the school's writing center. By day, he tutored students in the finer points of grammar and compositional skills, and learned all he could about community college administration from Dean Anderson. In his spare time, he worked toward a Student Affairs in Higher Education Master of Science degree from Colorado State. It had taken four years of hard work and a lot of trips between Greendale and Fort Collins, but he'd graduated with honors, and when Dean Anderson retired two years later, Pelton's years of preparation and his obvious (and obsessive, some said) love for the institution made him the logical choice to be the next Dean.
The new dean was firmly convinced that Greendale Community College could be a first-rate institution of higher learning, but was all too aware that most people didn't see it that way. But he was sure that with enough effort on his part, people would eventually come around to his point of view. And so, as he liked to say, he beat on, a boat against the current, but one who refused to be borne back into the night, at least not ceaselessly. (He had written his senior thesis on Fitzgerald.)
At the beginning of each school year, the dean would make two lists, one that ranked the incoming students in order of physical attractiveness, and another ordered by how helpful they might be in improving Greendale's reputation. He had found a few gems among this year's crop, many of whom, oddly enough, had ended up in a Spanish study group together: Troy Barnes, a former high school football star who was just what the struggling Greendale football program needed; Annie Edison, a real go-getter who could always be counted on to volunteer for pretty much anything; Pierce Hawthorne, the fifth richest man in the state and thus a lucrative source for future donations to the school.
And then there was Jeff Winger, who was near the top of both lists. Jeff was a very attractive man, and one who positively oozed charisma. He had founded and seemed to be the leader of the Spanish study group Barnes, Edison, and Hawthorne were part of. And what a speaker! Winger had a way with words that could convince a legless man to get up and walk. The dean had never expected to find himself nodding in agreement as he listened to someone compare his beloved school to an insane asylum, but that's how good Winger was. Unfortunately, that comparison was one of the nicer things the dean had heard him say about Greendale; Winger's attitude toward the college ranged from grudging tolerance to seething hatred, and with that kind of attitude, Jeff was unlikely to be of much use to the school. Still, Pelton had to try. He had, quite to his own surprise, successfully blackmailed Jeff into convincing Troy to join the football team, but that wasn't a trick he'd likely be able to repeat. So he took to observing Jeff more closely, now looking not just at his body but also for a way to break his resistance to supporting his school.
It was about a week later when he spotted what could possibly be a chink in Winger's armor. He had seen Annie Edison confront Jeff in the hall and demand that he attend a Mexican Halloween celebration she was throwing in the library. Winger had refused at first-which was a little surprising, as Annie was a very attractive young lady (albeit in a buttoned-down way sort of way) and Jeff struck him as the kind of person who would really enjoy a Mexican Halloween-but to the dean's astonishment, Jeff relented almost immediately as Annie burst in tears in front of him. And hadn't he just seen the pair together outside the pep rally a few days earlier, Jeff's arm slung around Annie's shoulders?
He thought maybe he'd misread the situation when, a few weeks later, Annie was unable get Jeff to join her on the Greendale debate team. A bribe had ultimately done the trick, but getting him on the team turned out to be only half the battle. The dean had watched with disappointment as Winger put forth next to no effort in the debate against City College despite Edison's obvious disapproval. Afterward, though, he happened upon City College's star debater, Jeremy Simmons, taunting Jeff and Annie in the hallway outside the gymnasium. His attacks on Jeff had no effect, but as Simmons turned his acid tongue on Annie, Jeff's entire demeanor changed. With a single glance at Annie's crestfallen face, Winger let loose on Simmons and led Annie away to prepare for the conclusion of the debate. Interesting.
And then, the kiss. Oh God, the kiss. The dean had rarely seen anyone as gobsmacked as Jeff after Annie kissed him to win the debate. But it wasn't that deer-in-the-headlights look that excited him so much, it was the look that followed. It was a look that mingled embarrassment and fear, that communicated quite clearly that Jeff had never considered that there might be someone with such power over him, and that he had no idea as to how he might be able to keep it from happening again.
That settled it. If Jeff Winger was a man who could get anyone to do anything he wanted, then Annie Edison was Jeff Winger's Jeff Winger. His weakness in the face of her distress and his obvious attraction to her meant she, and perhaps she alone, could convince Jeff to use his talent and his influence for the greater good of Greendale. As the weeks passed, though, it became evident that there were limits to Annie's influence. Jeff had displayed no interest at all in the STD Fair despite Annie's obvious enthusiasm for it. It seemed that unless she was visibly upset, or was kissing him, Annie was no more able to get Jeff to do something than the dean was. The former was not of much use; Jeff knew better by now than to antagonize her himself, and jackasses like Jeremy Simmons were in short supply.
As for the latter, it seemed as though Jeff was going to pains to avoid acting on his obvious attraction to her. In fact, Pelton had watched Jeff flirt with his assistant Sabrina right in front of Annie. (Of course, even if he had tried anything with Annie, she might well have died of embarrassment, if her reaction to the anatomically correct penis model was any indication.) Their time together in Group Study Room F notwithstanding, Jeff was spending time with everyone but Annie, even Ben Chang, of all people. Which was a problem. If they were never together there wouldn't be any kissing, and he needed them to be kissing. He was going to have to take matters into his own hands.