for the 5 headcanons - Charlie!!
Send me a character and I'll give you 5 headcanons!
Helped pick Deanna's name
When his mom was pregnant with Deanna, little Charlie (like 6 or 7 at the time?) got to help her pick out his little sister's name and he was so excited and so honored to do that. She gave him a short list of names she was choosing between, and Charlie got to have the final say. He didn't even hesitate, he knew it was gonna be Deanna the second he saw the name, even his mom made him think about it a bit longer to be sure. Deanna really likes hearing this story when they're older.
Assistants and birthdays
There's that line in season 3 or so about the book some guy wrote with a bunch of false rumors that leads to Sam asking Charlie if he attended Carol's birthday party where they "did a seance to talk to Margaret's grandma" and Charlie says no. The only reason he wasn't there is because he doesn't fuck with ghosts. Charlie gets invited to every birthday party or general get together the assistants throw, and he goes to most of them, just not if there's ghosts (and that actually does cover a surprising amount of things Carol and Margaret throw; he's concerned sometimes but not concerned enough to see what's up). Charlie's especially close with Donna and Bonnie, but he loves all the assistants really. He gives really good gifts, too? And the five of them also always make sure they get Deanna something for her birthday (once Deanna got invited to a ghost party; she said yes, Charlie said no).
COS to his chosen President
Now I got this idea from a jazzjo fic where he does it for Andy, but I can see it happening with CJ just as easily, or lbr a totally new character. Charlie eventually does for Andy or CJ or anyone what Leo did for Jed Bartlet and what Josh did for Matt Santos. He picks her himself, based on the work she's already doing and she ideas she already has and that X factor that Debbie saw in him, Leo saw in Jed, Leo then saw in CJ, Josh saw in Matt, and so it goes. He convinces her to run, he has a plan ready to go if she's just ready to execute it, and by this point in time he's old enough that he's turning a little grey by the end of the campaign (but you'd never know cause man dyes it well) but he runs her and he gets her elected and there is something so damn special about the day he walks back into the Oval Office from the COS office that's now his, to a President sitting there entirely because he knew she should be there. (If Leo could see him... but Josh is proud enough for two.)
Kids with Zoey
Zoey wants three kids to match her and her sisters, and they end up with four because the last one's a bit of a happy accident. Three boys and the accidental girl. Charlie loves being a dad, though he does have the same struggle to a degree that most dads in the show tend to have, where there are absolutely times where the job takes priority over quality time; he's better at managing the balance, though, and it's the kind of thing Zoey was more or less expecting to a degree. One of the boys (entirely stolen from @jessbakescakes) is called Charles Josiah, CJ for short, and Jed and CJ are never going to stop comparing who that kid's more like between the two of them.
Deanna's graduation
Charlie cried at both Deanna's high school and her college graduations. There was no stopping it; he was both so proud of her, and it just really hit in that moment too that their parents are never gonna see her do these great things. He's not ashamed to cry in front of Deanna in those moments, but also when he got back to the White House (or wherever after her college graduation), the guys will never hear about it. Deanna tells CJ, though, which is also when she drops off that picture Charlie ends up putting on his desk.
