It was an average and unusual Saturday night all at once for Jeff Winger. The end result was fairly conventional, as he returned home from a night out with a woman ready to sleep with him. But the unusual part was that although the woman didn't give out her age, it was clear she had a few years on Jeff. All he knew for certain was that her name was Carol, she had short brunette hair and blue eyes, and it was safe to assume she was somewhere in her mid-40s.
This addition to the Jeff Winger wall of fame didn't exactly fit in with most of the others. If Jeff was actually looking to get some action when he set out for the night, he probably wouldn't have given her a second look. But with his guard down and his playbook shelved for at least the start of the night, Jeff actually let himself talk to this older woman and grow to….tolerate it. She was a sharp number with a bit of an upper class tint to her, and a spark of youth that was hidden underneath those noteworthy eyes.
By the time they got to the drinking portion of the evening, Jeff figured he could pull the playbook out for a while to finish the job. And since he didn't need it that much by this point of the courting, it was an easy sell. So although the night had a few unusual twists to start off, it ended like most good ones; with a satisfied Jeff out cold by the time he finally let the both of them wear themselves out.
It was a good thing the drinking ran its course by the end, or else Jeff might have wondered just why he let his guard down for an older woman. He might have caught the irony of being the younger member of this tryst, after…..being on the other side in other…..connections. He might have even taken more specific notice of the color of Carol's hair and eyes than he meant to. So it was a pretty good thing that the drinking did run its course.
That course ended the next morning with Jeff waking up to the usual side effects. It ranked in the middle tier of his post-sex hangovers, so it was nothing he couldn't handle. Plus it seemed that Carol wasn't in his bed, so it looked like he wouldn't have to send her home and add any annoying awkwardness to the hangover. A tinge of something other than relief came to Jeff at that thought, yet he brushed it aside to keep the annoying awkwardness at bay.
Other than that, the evening couldn't have gone better even if he planned it out from the start. It went well enough that he could brush aside his….change of pace just this once. Still, it was probably best to not include this among his next group of sex stories to the study group. He imagined the age thing alone would give Pierce, Shirley and Britta enough joking and nagging material to last a week. As for the rest of them…..it probably wasn't worth imagining. Annoying awkwardness and all.
After getting himself dressed, Jeff headed into the living room and got a taste of that awkwardness after all. A fully redressed Carol was sitting on his couch to start it off, which explained why she wasn't in bed earlier. It looked like she had indeed gotten herself ready to slip out, yet she was still here; perhaps because she had gathered every picture, story and piece of memorabilia he had in this room of Greendale and the study group.
"Good morning, Jeffrey," Carol said when she finally looked up to see him gawking. "So this is what you've been doing in between lawyer jobs, I see." All right, so his line about being in between jobs as a lawyer didn't hold up anymore. And she actually knew that he was in Greendale now, which sure as hell couldn't be promising. But then again, they had already finished their night and these horror stories might scare her out of here faster.
"Yeah….it kills time about every four months, what can I say?" Jeff started off, as he tried to reboot his hung over brain for more clever one-liners.
"I'm sorry to pry. It's just that I saw all these interesting items around here and I had to look closer. After all, I've heard Greendale is….quite a unique institution," Carol stated, using perhaps the nicest possible words for Greendale. But before Jeff could give her a few Greendale nightmares, Carol held up a picture of the study group to throw him off. "Are these friends of yours?"
"Study group, technically," Jeff got out, even less eager to talk about them to a one-night stand. But he figured he should at least say their names and then segway to a few easy Dean Pelton jokes. "That's Britta, Abed, Troy, Shirley, Pierce and Annie….can't really study or survive the likes of Dean Pelton without me, really. Speaking of which-"
"Annie….something about that sounds familiar," Carol interrupted, as she seemed to have this sixth sense on how to throw Jeff off his best-laid plans. Before Jeff could regroup again and get this conversation on any other possible path, Carol kept going. "I remember reading a few years ago about an Annie who freaked out at her high school and ran through a window on Adderall. I think she was heavier than this girl, but the face still looks familiar. What was her last name….Edwards, Evans…."
"Edison," Jeff muttered before he knew what he was doing. Once he figured it out, he shut his eyes in frustration and gave the rest away to his sharp interrogator. "Yes, that was it! So this is that same girl….my goodness, what a difference a few years makes."
"Yeah, rehab and weight loss can help out too. So anyway, let me tell you about that crazy Leonard-"
"I didn't mean a physical difference," Carol pointed out. "I mean, I read that this girl was on her way to an impressive Ivy League education and career. Now because of pills and rehab, she's in this….vastly different environment. It's heartbreaking, really."
"Well, rehab doesn't need to share credit with the pills. They screwed her up but rehab got her out of it. Her own parents didn't want her to go, but she went anyway instead of sweeping it under the rug. Crazy, I know, but that's the kind of crazy she is," Jeff went on before catching himself once again.
"I should say so. Especially when saying nothing might have made her look a lot better. It certainly would have sounded better than this Greendale….from what I've heard of it, it sounds like the kind of environment a girl like that would go even crazier in," Carol stated.
For the third time, Jeff answered her without really thinking, yet he was even less self-aware of his words now. In fact, there was a bit of an offended tone in them this time. "It's kind of the other way around, when you really think of it. There are about 30 different levels of crazy there, and she's hardly in the top tier. In fact, she's usually the one that stops it from going to 40 or 50 levels. Granted, she's not as good at it when it comes to her precious GPA, but other than that she's the sane one! Sometimes not just by Greendale standards!"
The combination of Jeff's hangover, and his usual lack of inner filters when Annie is involved, led him to list off all her major adventures in the last two-and-a-half years. Granted, it was a bullet point summary and he left out certain details from ordeals like the debate, the Tranny Dance, the Rich incidents, and certain parts of the conspiracy saga. But after this little three-minute presentation, Jeff figured he had described Annie's insanity in the best way possible; if not the least suspicious way.
"I see…..so being at Greendale made her do all that?" Now that Jeff's right mind was coming back, he decided to just nod and not reveal any more out loud. Just as Jeff realized how unsettling it was to talk this much about Annie to another woman he just slept with, he thought he heard Carol mutter something like "I should have known…." Yet as he remembered that Carol was still there, she finally got herself up and stated "Thank you for a wonderful evening and interesting morning, Jeffrey," before leaving the apartment at last.
Jeff's mind barely had the strength to kick itself, but it tried anyway. It was probably inevitable, since his last three-four women didn't bring about any thoughts of Annie and that was too long of a streak to last. This was the first time he actually mentioned her out loud to them, however; as if this latest tryst wasn't historic enough. And now that Annie was back on the brain, it was clearer to Jeff just how ironic this past pairing was when it came to age. Or it would have if he didn't force his brain to kick itself at full strength.
So Jeff focused on the positive aspects instead, and fortunately there were just enough of them. He found a way to get Carol to leave that didn't get him kicked or slapped, she was probably too creeped out just now to call again, she likely didn't have the connections to make his Annie-blabbing come back to haunt him, and he learned his lesson about leaving his Greendale stuff so exposed. All in all, this was still a pretty good outcome; it may have dropped off the top 20 Winger hookups at the end, yet it was safely in the top 40 for sure.
This let Jeff have a pretty peaceful Sunday and got him recharged for the wackiness to come on Monday. He arrived at Greendale fashionably late as always, refreshed and ready for whatever deranged class, Dean Pelton harassment lines and movie genre was waiting for him. As he approached the study room, he saw that everyone else was already there and Annie was leading the discussion, looking a bit frantic as she talked. So it was shaping up to be a regular day after all; as if just being Jeff Winger wasn't enough of a blessing today.
"Okay, so is a 99 in Biology or Geometry the end of Annie world today?" Jeff joked as part of his entrance.
"Jeff, where have you been? No, don't answer, there's no time for your gross sex stories!" Annie rattled off. She didn't even have a hidden little smile for his joke….first out of the ordinary thing today, but not else to make it not normal. "Now I have to go through the whole thing with you, and I just got done drilling them!"
"Note how I didn't say I drilled Julie Newmar after that! See, unlike Jeff, I was paying attention!" Pierce boasted as obliviously as usual.
"Uh huh. So what do I have to keep ignoring, exactly?" Jeff asked in full monotone mode.
"Annie's mother called her and said she's coming to Greendale today," Abed explained. "Therefore, Annie's asking all of us to be on our best behavior, or else she'll ridicule her for her life choices more than usual, or worse. I'm supposed to quote only three movies or shows at most, Pierce has strict instructions to stare at her hair and no lower, Troy's going to pretend to be mute, Shirley's been confiscated of all but two crucifixes, and Britta will try in vain not to rant about how Ms. Edison gave matriarchal rule a bad name."
"You will realize it's mostly her fault if I slip up, right? I mean, this is a woman who ignored Annie's cries for help and cut her off just for saving herself in rehab! Not that rehab is the best solution to cure all addictions, and not that some drugs don't need to be rehabbed out, and-" And thus the usual Britta groans ensued to bring the day back to normal.
"Britta, that's coming out of the free rant time I promised you after Mom leaves!" Annie promised before turning back to Jeff. "Jeff, we don't have much time before she gets here, so I can only tell you not to do anything….creepy, okay? Don't hit on her, don't use your darkest one-liners, don't say anything about why you're not a lawyer! In fact, don't do anything to make her ask why I went to rehab, just to end up hanging out with someone like you, okay?"
"Annie…..since Abed can only mention movies three times, I guess I have to ask this for him. Are you doing the old 'I'm ashamed of my friends because I'm trying to impress someone who dumped me, unlike those friends I'm ashamed of' plotline? Because I don't have the energy to go through that on a Monday," Jeff explained as Abed nodded his approval for bailing him out.
"No, I'm not ashamed of you! And yes, I know it's stupid to impress someone who cut me off! But I just want to avoid fighting with her for once. She caught me by surprise already when she called yesterday and said she was coming over! I don't know why she's coming now, but just in case it's to make me crawl back home and transfer, I'd rather not give her more reasons to do that! So please, don't inspire her to nitpick my life that much!"
"Annie, if it means that much to you, I won't do anything. I'll just stay quiet, give her short answers, try not to get involved in something personal, and spend just enough time texting to not screw anything up. It'll be quite a challenge for me, but I will try to pull it off the best I can," Jeff said in full-on sarcasm mode.
"Yes, that's perfect! You should probably do 20 percent less texting, but other than that, it should keep her from getting too much ammo on me! Thank you, Jeff!" Annie exclaimed in full on sugary sweet mode. That almost made Jeff go into Annie smile mode, yet he quickly realized that he really needed to tone those down around her mother. So maybe just 5 percent less texting would help him keep that under wraps.
Just then, Jeff heard a knock on the study room entrance and then saw Annie's big Disney smile slip into a somewhat more forced, slightly less big smile. "Oh….hey Mom!" Annie said to help explain the change before she got up from her seat.
"There's my little Annie!" When Jeff heard that, the first thing that came to mind was how calling her "little Annie" didn't get this mother character off to a good start. The second thing was that this condescending statement had a somewhat familiar voice to it.
The third thing didn't come through to Jeff in time…..since his brain utterly collapsed when he turned around and saw Annie hugging Carol.
Jeff stayed stuck in a mental coma for a few seconds until the two broke apart. But when he finally saw just how similar the two really looked face to face, he wished he was back in the coma and the plug had just been pulled. "Everyone, this is my mother, Carol Edison," Annie somehow said loud enough for Jeff to understand.
"So this is the study group that the crazy bald man impersonating a dean talked about," Carol commented. Annie's smile got a little more strained, although it looked positively normal compared to Jeff's frozen expression.
Jeff tried in vain to move his face by at least an inch when everyone else said hello. Carol smiled politely and nodded at all of them…..then when she gazed at Jeff, her smile went up by just an inch or two. That was a very familiar smile, and not just because Jeff actually remembered it from Saturday night. It was the same secret, satisfied, all-knowing, seeing through Jeff smile that Annie haunted him with every other day….which made all the sickening sense in the world now.
Somehow, Jeff stopped himself from vomiting and tried to keep thinking. This yielded at least one positive thought, in that Carol wasn't shocked to see him here and was less likely to do something irrational like….share some things with Annie. She already knew Jeff and Annie went to Greendale together, and she had a whole day to make sure she didn't give anything away about her first time – meeting – with Jeff. And if she was Annie's mother, she was certainly smart enough to stay quiet about this.
Unlike Jeff….who just told her almost every single thing Annie ever did at Greendale yesterday morning. Unlike Jeff….who told embarrassing Annie stories to a woman that wanted Annie's past problems kept quiet, because of how bad it would make her and her family look. Unlike Jeff….who told Carol every single bit of material she would need to make Annie's life a living hell today. Unlike Jeff….who most likely directly inspired Carol to come here and try to take Annie away from Greendale and all her friends.
Oh, and unlike Jeff who slept with Annie's mom after a few hours, after doing everything he could over the last few years not to sleep with Annie too.
Yep, vomiting sounded pretty good right about now. But since Jeff couldn't hear a damn thing over his head coming apart worse than in any hangover, how would he know?