57Before attending Greendale and meeting the study group (or more accurately one particular study group member), Jeff had only been in love one other time in his life.
It was when he first attended college. Not Greendale Community College, but the University of Denver, where he had gone to get his undergraduate degree the first time around. He was sitting in his English lit class when a tall gorgeous woman with flaming red hair walked into the room. He assumed, like him, she was a freshman and offered her the empty seat next to his. She said that was sweet but she had already taken the class her freshman year, before announcing to everyone that her name was Megan and as she was the T.A., she was available for tutoring if the need should arise. Not to be deterred Jeff quickly recovered and formulated another strategy, which was to ask her to tutor him. She agreed and they began meeting once a week to go over the material.
Though she was a believer in working towards your goals, Megan felt it should only extend to what matters to what you want to do. And if you had to do something that wasn't directly related to your goals, such as take a class that was simply a freshman requirement, it was all right to cut corners in order to get ahead. Which was why the help she offered Jeff during their session was less about pure learning, and more about her telling him what kind of questions were specifically on tests and giving Jeff specific information to use on projects and papers. At first Jeff was worried he'd get caught and would be kicked out of the class or even expelled. But as the weeks went on and nothing happened except the teacher being impressed with Jeff's results, Jeff stopped worrying about it. Instead he saw that Megan was right; as long as he got results, it didn't matter how they were achieved.
Although getting a free ride in the class was nice, Jeff didn't forget his main reason for wanting to meet up privately with Megan. He flirted heavily with her during their meetings, complimenting her on everything from her looks to her deviousness. At first she'd just smile and tell him to pay attention to what she was telling him. But eventually she found herself being won over by the charming freshman. They ended up going to an off campus party, which led to a hot hook up in one of the bedrooms.
At first their relationship didn't consist much beyond sex and her helping him cheat. But after a couple of months Jeff found he was developing feelings for Megan. When he brought it up to her she said she liked him too, but didn't want to define their relationship or talk about the future. She was a junior and he was a freshman and that left things too uncertain for them. She told him they should just live in the moment and enjoy what they had now instead of worrying about what might come later.
But despite her initial reasoning, Megan found herself caring for Jeff beyond him being just a guy she simply hooked up with. She still didn't want to look too far ahead, but she started realizing she thought about him in terms akin to a boyfriend. This continued when she met Jeff's mother during Family weekend, and overheard him tell his mom how crazy he was for her. It made her happy and gleeful to know both how much he cared about her and that he wanted his mother to know.
Their relationship continued to grow and flourish as time went on. When they began their second and fourth year they moved into an off campus apartment together. At first it was fun cohabiting together. But after a while Megan began to grow uneasy as the reality of their situation hit her. She was a senior and was set to graduate in May, while Jeff was a sophomore and had two more years of school left. While she loved Jeff, she wasn't sure how well it would work with her in the real world while he was here. She hated that she had gotten herself into this situation, since she had sworn she wouldn't allow it to happen. But she was in a tough dilemma. She loved Jeff greatly, but she also didn't want to hold him back. And as much as she hated feeling this way, part of her worry extended to him doing the same thing to her.
They talked about the reality of their relationship, and Jeff assured her that he wanted to be with her no matter what. If after May they had to endure a long distance relationship until he graduated in two years he was willing to do that. She tried to make the case that it was hard and that she didn't want to drag him down, but he finally convinced her that it could work.
While he knew he had convinced Megan to continue their relationship beyond her graduating, Jeff truly wanted to prove to her just how committed he was. Which was why he searched several jewelry shops until he found an engagement ring that was elegant and affordable. Jeff knew they wouldn't marry until after he was done with college. But he wanted to show her how serious he was, and how invested he was in their relationship. So he arranged to propose to her two days from her graduation ceremony. He made reservations at the perfect restaurant, arranged for a string quartet to play their favorite song, bought a new suit and rehearsed exactly what he was going to say. He knew this was a difficult time for her. He had caught her crying when she didn't think he was around and her nerves were so on edge she was throwing up every morning. But he hoped once he assured her of their relationship she would be less fearful of losing him.
When the big day arrived Jeff went out to make sure everything was tip top before going back. He had been so happy as he drove back to their place with the ring in his pocket. Once he arrived he got out of the car and walked in, ready to tell Megan he had a big surprise. Instead he received the shock of his life when he saw that she wasn't there, along with all of her stuff.
At first he didn't believe that she had just left him without a word. But all his attempts to track her down were futile. He went to the registers and learned she had officially left before the graduation ceremony. He tried to call her parents but they wouldn't tell him anything. He even went to their house to try and see her, but they sternly refused to let him onto the property. It finally hit him like a battering-ram; Megan didn't want to be with him anymore.
Jeff was beyond devastated by their breakup. After his father had left he didn't believe in romantic love or monogamy. After meeting Megan he took a chance on love, and truly grew to believe they were meant to be together. But in the end, all their time together had served to do was reinforce to him that love was a lie and we were only meant to be alone.
He returned to school after the summer for his junior year, but ended up dropping out after less than three months. He just couldn't focus, and it was too hard being around all the memories of the two of them together. Afterwards he floated around for a while, until he decided to follow through on his plans to be a lawyer. He didn't need a bachelor's to practice law. And if there was one thing Megan taught him, it was that in the long run it didn't matter if you cut corners on the unimportant things, if it meant your goals came true. So Jeff lied about having obtained a bachelor's degree and cheated on the LSAT. From there he got into and graduated law school, culminating in securing a position at Hamish, Hamish and Hamlin. For years he rode that wave of success as he won a large number of improvable wins. But eventually his lie was found out, and he lost his job.
Jeff ended up going back to school to get his bachelor's degree legitimately, this time at Greendale community college, where he met the six people who would change him for the better. They taught him to trust and care about others again, and more importantly he learned he no longer liked being alone.
Of course, of all of them the one who changed him the most was Annie. At first it was easy to ignore any romantic feelings towards her, especially since she was so different from the first woman he had fallen in love with. Annie was studious and believed in always working hard for your goals, without ever cutting corners. And she very much liked planning out her future. But despite his resistance, she managed to work her way into his heart. And after a while (far longer than it probably should have taken), he finally relented and accepted that he loved her. Things were rocky at first, since she herself wasn't sure they should be in a relationship after everything he put her through, but he was able to convince her that they belonged together.
Things with Jeff's second major relationship progressed much the same as they had with his first one. He introduced Annie to his mother and they eventually moved in together. And while he had once drunkenly stated that marriage was a lie, he shocked everyone except for Annie (and Abed) by proposing to her a year and a half after they became a couple. Jeff had truly become a happy man.
But while he loved Annie with all his heart, there were brief moments he found himself thinking of Megan. He wouldn't trade being with Annie for anything. But there was a part of him that wished things had gone differently with his first love, and that he at least knew what made her leave him without ever saying a word to him again.
What Jeff never expected all these years later was to get his answer, and so much more.