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sing with Jeff Winger
It's true that Craig might have crossed a line or two with this one, by doing things such as invading a student's privacy and then using that information just to get Jeff to spend the day with him. But Jeff wasn’t totally free of guilt either - he pretended to be sick, at the hospital, as an excuse to get out of helping his friends! And besides, had it really been that bad? Didn’t he and Craig end up creating amazing memories together? Jeff even admitted he had fun after their incredible performance singing Kiss From A Rose by Seal.
Sure, when Craig let slip up that he actually read Jeff's personal email it all went downhill from there. But it was pretty great while it lasted. And plus, he got many retweets on their karaoke video after.
dance with Jeff Winger
Craig can't say this one was completely unexpected or else he wouldn't be wearing that strapless dress underneath… His other dress. But it was still a huge surprise that Jeffrey immediately chose him as his tango partner for the Hunger Deans competition. Of course, that way he was also just bound to win that challenge. Unless Jeff had been a sloppy, uncoordinated dancer, which Craig knew perfectly well he wasn’t.
Also - the fountain worked!
get a genuine compliment from Jeff Winger
After they became close friends, closer than Craig ever thought they would get, he found out that the intensity of his obsession with Jeff actually cooled down. He guessed it was because before, Jeff was this impressive, emotionally distant stranger who he couldn’t help but idolize. But after really getting to know him, Craig finally understood he was just like any other person. An exceptional, extremely attractive man that he was still very much into, yes, but just a person nonetheless.
Which is why Jeff’s revelation that he had been thinking that Craig was beautiful - in an attractive way - didn’t affect him as it probably would have a while ago. Craig was still flattered, of course, because he still thought of Jeff as the epitome of beauty, but it mostly just made him genuinely happy that they had gotten to a point of intimacy where Jeff was willing to confess that to him.
dress up with Jeff Winger
Jeff had actually asked him about his costumes, while in Craig’s apartment, during the time Craig hadn’t been wearing them as much. He realized Jeff did it as a way to cheer him up, and that was one of the happiest moments in his life.
But then it got even better somehow. Craig used some of their time together to explain about the costumes and what they meant to him - some of them were just kind of silly, some of them were to be used for… private matters -, but others were really elaborate and had real sentimental value. Some of them played a big part on Craig’s confidence and in him feeling comfortable with himself.
So one day, Jeff casually mentions he’s been curious to try it out, too. Luckily, Craig already had Jeff’s measurements noted, so he could make this a surprise. He ends up making something resembling a suit, because he knows that’s what Jeff would be most ok with, but it’s much more flashy and fun than a regular one.
Jeff is stunned when Craig presents it to him. He says he likes it, and he even lets Craig apply some makeup on him to go with it. He’d done it before, once, while they were joking around - and Craig wouldn’t mention it loud out as not to scare him off from giving this another try, because he knows how self conscious his friend can be, but Jeff had actually seemed to enjoy the way bright blue eyeshadow looked on him.
Craig also wore a costume, something to match Jeff’s, obviously. And it was fun, even if they just stayed in the apartment. Jeff did end up agreeing to wearing it again, with Craig, someday, during a Greendale dance. And he would never turn a suggestion like that down, obviously! That kind of scenario would be a dream come true. But really, the fact that Jeff was willing to partake in something that he himself didn’t really understand, but that he knew Craig loved so much, was more than anything he could ask of him.
hold Jeff Winger's hand
Jeff usually leaves Greendale earlier than the Dean, but there was this one day when he stayed after he was done with classes so he could work on some papers that were… Long overdue. He was trying to be more responsible with his assignments from now on, he had told Craig. Craig was trying to do the same.
So Jeffrey ends up stopping by his office later, so they can ride back home together. He stands by the doorway and asks, “ready to go?”
Craig puts a finger up. “One moment, Jeffrey.”
“Really? If we don’t go now we might as well just wait here to open the school for tomorrow.”
Craig scoffs at him. “It’s not that late. I would’ve been gone much earlier if I had to take the bus, but since you offered to give me a ride…”
Jeff approaches his desk. “Oh, so you’re taking advantage of my nice gesture?”
“That’s not what I meant!”, Craig protests. But then he seems to consider Jeff's point and starts to gather all the papers on his desk. “Alright, alright, let me just put these in the cabinets and turn all the lights off and I’ll be good to go.”
Jeff sits in one of the chairs by the desk, grabs his phone and waits for the Dean to organize everything. He looks up from the screen from time to time to make sure Craig is still actually getting ready to leave. When it seems like he’s done, Jeff gets up and puts his phone away in his pocket.
Suddenly, Craig hesitates, and starts to say, “oh, wait-”.
But Jeff has waited long enough. It’s really late, and they both should’ve been home long ago by now. He simply replies a “no”, grabs Craig’s hand and leads him to the parking lot. He doesn’t let go of it until they’re right in front of Jeff’s car.
kiss Jeff Winger on the cheek
Craig, Jeff, Frankie, Elroy and Chang had been hanging out at the bar on Fridays. It was a fun end of the week activity, and it was also a nice opportunity to pay a visit to Britta. They didn’t always drink much there, it served mostly as a place outside of Greendale where they could talk and have some fun together.
Sometimes, though, they did drink. Surprisingly, Jeff had been the one to stay out of it during the occasion, promising to drive everyone home later, as he was committed to reducing his drinking habits. Besides, it was pretty fun to hear his friends mumble embarrassing things that only he would remember later. It was also interesting to notice how Craig seemed to be staring at him more and more as the night went on.
Craig had the biggest smile on his face when he turned to Jeff and said, “You think I’m beaaautiful.”
Jeff laughed. “Yeah… I said that, didn’t I?”
Craig nodded, over and over. He reached out and put a hand on Jeff’s shoulder. “Can I tell you a secret?”, he whispered, or at least tried to.
“Sure”, Jeff replied. Craig’s face was mere inches from his.
“I think you’re beautiful too.”
“Hm... Pretty sure I already knew that.”
Jeff smiled at him. Craig kissed his cheek. Luckily for them, no one was paying attention. Even if they were, Jeff doubted they’d remember anything from that night. Craig certainly didn’t when he woke up the next day, sleeping on Jeff's couch. He'd told him Craig could not, for the life of him, find his keys last night, so Jeff had to take him into his apartment, and then he explained everything that happened at the bar. He even made him breakfast too, so maybe "accidentally" dropping his keys in Jeff's car had been for the best.
kiss Jeff Winger on the lips
When Jeff actively asked about his bucket list, Craig kind of freaked out. He had mentioned it once, as a joke, but of course it existed! And of course it contained Jeff Winger’s name multiple times.
So naturally, Craig at first thought that that was a trap, that Jeff finally realized he was a weirdo or something, and they were going to stop hanging out and having fun and talking to each other… But then it turned out Jeff actually wanted to kiss him? Actually kiss him. Never in a million years Craig would’ve dreamed… Well, in his dreams, sure, it did happen. But Craig genuinely didn't think he'd have a chance in real life, much less that it would be Jeff's idea.
And so, they kissed. Timid and brief and experimental at first. And it was nice.
So nice in fact, they just kept on doing it.
have Jeff Winger in his bed
Craig did always wonder what Jeff would look like laying on his bed. Not even only in a sexual way, but just the idea of having him in his apartment, inside his bedroom, on his bed... It just seemed so intimate.
When it finally happened, it did feel like a dream. But Craig couldn’t close his eyes in wonder at the time, because Jeff was visibly nervous, and Craig needed to be wide awake and grounded to help him through it. They were discussing what was going on between them - with all the affections, and kisses that had been taking place recently -, and if they were in fact, heading towards the path of a relationship.
Craig knew very well how the talk about commitment scared Jeff. He hoped that wouldn’t make him run away. He thought about how he wanted Jeff to spend the night over, and how much Craig would love to wake up in his arms. He hoped he wasn't getting ahead of himself with that.
Fortunately, he wasn't.