It took some time for Jack to actually accept having a sleepover at his dorm room, but when you finally asked (again), he accepted with a grunt and a wagging tail. It was clear he didn't want to look too excited for it, but his tail always gave him away.
You definitely were having pretty much fun, and even if he felt a little awkward at first, you ended up helping him to relax a bit. He even showed you his cacti and talked about it, then you two played board games, chatted, etc.
However, before you expected him, you already had him trying to keep his eyes open and hold back those loud yawns of his. Of course... He usually went to sleep at 10 p.m. and it was already 12 a.m!
"..Mngh... I still can keep up, y'know?" He grumbled, a slight smirk still on his face as he could barely keep one eye open. You insisted on him going to sleep... but this was his first sleepover and, surprisingly, he was having more fun than he thought.