A series of one-shots, in no particular order, chronicling the day-to-day moments of the Charmings and their ever-extensive family. Some AU, but mostly canon.

(Captain) Charming Cobra. Old man jokes aside, Killian really has been around for a long time. It's too bad nobody has a clue just how long. Post 4A

Disclaimer: OUAT is not mine. I just play with it.

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Henry didn't know what made him ask that particular question in the first place, though he was tempted to say it was Killian's complete lack of an answer. And while he wasn't entirely sure any one person would know the answer, including the pirate in question, Henry had taken it upon himself to dig around Storybrooke to try and find out just how old Killian was.

Emma knew Killian's history, but she didn't have a clue about his age. She joked that he was born sometime between the pharaohs and the dinosaurs, and probably knew a few of them personally.

The only person alive who had met Killian centuries earlier was Grandpa Gold, but he was banished from Storybrooke, so those potential answers were long gone.

Belle had been surprisingly helpful. She filled in a lot of the history Henry wouldn't have even known to ask, like where his father Neal fit into the timeline and his great grandfather Peter Pan (That still took a little getting used to, knowing the fabled boy that never grew up was his great grandfather).

And while Henry didn't necessarily think David would know the answer, it wouldn't hurt to ask. Maybe he knew someone who had a grandfather that sailed under Hook back in the day. So while they ate lunch at Granny's, Henry digging into a burger and David alternately stealing French fries and holding a formula bottle for baby Neal, Henry decided it was as good a time as any to ask.

"Hey grandpa, how old do you think Killian is?"

"Huh?" His grandfather was startled out of whatever daze baby Neal had over him, accidentally jostling the baby bottle from the infant's slight hold. Henry was convinced infants had their own brand of magic that could hold adults in a trance. He had yet to see a hero or villain who didn't start fawning over his baby uncle when he was brought into a room. If rumors were to be believed, even Zelena had cooed to the baby when she'd kidnapped him.

Neal didn't seem to like the loss of attention or his newfound lack of baby formula and gurgled unhappily until David replaced the bottle in the infant's mouth. The man whispered softly to his son, soothing the baby but still not answering the question posed to him, so Henry continued.

"I mean, he's three hundred something, but three hundred and what?"

David's face curled uncomfortably as his gaze shifted between his son and grandson. "Honestly Henry, I don't really like to think about it, especially when I think of how old everyone in this town is supposed to be. We were all frozen in time for nearly thirty years. So I'm in my fifties and have a newborn. That's not exactly normal for anyone."

"I know, but-"

"And you know, technically your schoolmates are at least thirty years older than you."

It was Henry's turn to twist his face. He'd never thought about that. But it was true, wasn't it? He never made the connection during the first curse, but his classmates didn't age up through the grades with him. They stayed in the same classes while he got older, but no one noticed or said anything.

"Does that mean they took the same exact math tests every year?" Henry thought aloud. That earned him a laugh out of David, who did his best not to shake so much for fear of jostling the baby again, but was having a hard time containing his laughter.

"I bet they all got really good at those tests. Practice makes perfect, right?" David managed to say between chuckles.

Henry grumbled, "Damn it, that's not even fair. I had one go at those tests, and they had years of practice."

David shot him a look. "Don't curse."

"Killian curses," Henry muttered under his breath.

"Killian can censor himself just fine even after three hundred years of verbal piracy. I think you'll manage."

Henry leaned forward on the table toward his grandfather, indignant. "Ok, fine, but three hundred and what years?"

"And we're back to that again," David sighed.

"Neverland and all the curses kept him looking young, but for all we know he's older than Grandpa Gold."

David's eyes bulged comically. People continued to mill about the diner while Henry watched the range of thoughts play out on David's face.

That Hook could be that old had definitely never occurred to his grandfather. It hadn't occurred to Henry either until he started trying to put together a timeline. Somehow, it was easier to imagine Rumplestiltskin as being centuries old because he was the Dark One, and the Dark One was supposed to be an ancient being. Not to mention Gold was Henry's grandfather, so mentally adding a few years to someone who was supposed to be older was easy. But adding those same years to someone like Hook…

"Grandpa, think about it-"

"No thank you."

"-He went to Neverland back when he was in the navy, and Great Grandpa Pan was already there but we don't know for how long-"

"Back up. Great Grandpa Pan? Grandpa Gold I get, but Pan…" David's voice trailed off, incredulous and confused.

Henry shrugged. "Well yeah, he was a villain and had me kidnapped and all that but he's still family. Look, I'm trying to work out a timeline here, and it starts with Pan. I gotta write this down."

Grabbing a pencil from his trusty backpack, he pushed his half-eaten burger aside and set to work writing on the placemat. A line was drawn straight across the middle, book-ended by 'Pan arrives in Neverland' on the left and 'Emma breaks curse' on the right. Dashes were put in place along the line with notes like '28 years of first curse', 'Dad born', and 'Dad in Neverland' with questions marks around it.

"Ok, so Belle said Grandpa Gold was just a kid when Pan went to Neverland, but she thinks he was somewhere between five and eight years old-"

"You asked Belle already?"

"-When it happened, and since Killian was already a pirate when he finally met Grandpa Gold but Gold wasn't the Dark One yet, that means Killian already spent some time in Neverland. But for all anyone knows Lieutenant Killian got to Neverland the day after Pan arrived. That's the earliest possible starting point. Or he could've gotten there a lot later. Belle said she didn't think my dad was born until Grandpa Gold was in his thirties, so there's a thirty or forty year stretch between when Great Grandpa Pan got to Neverland and when my dad was born that Killian could've gone to Neverland and turned pirate."

"Wow, I gotta say, you sound like you did a lot of research on this Henry," David noted in awe.

"But Killian didn't just start out as a lieutenant. It would take a couple years to rise through the ranks, right? How many do you think?"

"Oh, um, I don't know, five or six?" David guessed, taking the baby bottle from Neal and throwing a towel over his shoulder, adjusting the infant to burp him. "Depending on which navy he was in the conscription age could've been anywhere from fourteen to sixteen years old. You know, you're being really logical about this. Is this how you do all your math homework too?"

Henry ignored his grandfather's last thought in favor of furiously scribbling more notes on the placemat. "So if Killian got to Neverland the day after Pan arrived then the oldest Killian can be is seventeen years older than Grandpa Gold. At the youngest, he's twenty-three years younger than Grandpa Gold."

David stared at Henry uncertainly, his hand still gently clapping Neal's back. "Are you sure that math is right?"

Henry pressed on. "If Dad was about fourteen when he left the Enchanted Forest and ended up in Neverland, Hook would've been somewhere between twenty-six and sixty-six. He doesn't know how long he spent in Neverland after my dad left the island, but I get that it was a long time. And I know he worked with Grandma Cora when he finally left…"

"Grandma- You're joking right?" Neal finally managed to burp, making David's already comical expression even funnier as he cleaned the infant's face.

"Respect the timeline, grandpa. If I can figure out how old she was then that's more proof for how old Hook is."

David snorted in disbelief. "Word of advice kid. Never try to figure out how old a woman is, even if she asks you to guess. It's always a trap. Isn't that right Neal? You'll never be that rude, no you won't. You'll have better manners than to ask a lady something like that," He cooed into his son's ear. Neal chortled happily, oblivious to what his father was saying but happy to have his attention.

Henry could only stare, mildly impressed at the speed with which David's attention had gone from him to Neal.

Fine then, he would do the math for Grandma Cora in his head and on the paper. So however old Grandma Snow was, plus eight was how old Regina was, plus twenty was how old Cora was, then add the twenty-eight years for the curse that brought everyone to Storybrooke in the first place. Add the either twenty-six or sixty-six years Hook was definitely alive for, not including extra time in Neverland with his dad, and it turned out to be…

"Either one hundred and ten or one hundred and fifty," Henry muttered, not realizing he'd said anything out loud.

"One hundred what lad?" Henry whipped his head up to see Killian Jones standing right next to him by the booth. David was equally surprised and his wide eyes told Henry he'd been just as lost in thought with his infant son as Henry was in his quest for answers.

It was baby magic. Distracting baby magic. There was no other explanation.

"When did you…?"

"You and the prince were both so lost in thought you didn't even hear me and Emma come in. Now what's this about one hundred and fifty?" Henry saw Emma standing at the counter, paying for a bag of take out lunch. Hook leaned over the table to glance at Henry's scribbled placemat. He frowned when he realized what sort of timeline was written there and whom it pertained to.

"Ah, that again? I thought we'd settled that lad. There weren't exactly calendars in Neverland. I had no knowledge of the passing years until arriving back in the Enchanted Forest centuries later. There's no real way of knowing for certain how old I am."

"Yeah, but Killian, I figured out that you're at least a hundred and ten or a hundred and fifty, not including most of the Neverland time. And there's this window of forty years in the beginning so you're either seventeen years older or twenty-three years younger than Grandpa Gold."

"Seriously?" Emma chimed in skeptically, carrying her and Killian's lunch. "Killian might be older than Gold? I don't know kid…"

Where Emma was doubtful of Henry's mathematical discovery, Hook looked mildly horrified at the idea, but mostly just baffled. "Lad, are you certain your arithmetic is correct?"

"Pretty sure," He smiled at the pirate, suddenly inspired by a thought. "Hey, does this mean for your birthday we have to have a cake with at least a hundred and ten candles on it? Since that's the youngest you could be? Or should we just guess three hundred and something like you keep telling people, because that would be a really big cake."

Hook didn't respond, eyes forward and unseeing, completely confused at the realization that he and Gold were actually so close in age.

His mom rolled her eyes at Henry's questioning. "Ok kid, you're coming with us to the station. I know for a fact you have math homework you're avoiding, and as impressive as it would be to figure out how old Killian is, it's not gonna get those algebra problems done." Before turning toward the door she said a quick goodbye to David, and whispered a gentle 'bye bye baby bro' to Neal, who giggled at the extra attention.

Henry grumbled out a 'fine' before packing up his things and walking to the door with his mom and Killian, leaving his grandfather to finish the forgotten burger.

He thought he heard Killian behind him muttering under his breath "Older than the Crocodile?" but he could have misheard. Henry would have to dig a little deeper into his research to find answers. Maybe one of the Lost Boys would know how long Hook had been in Neverland? Not that Henry was entirely eager to see them again, but it was worth a shot.

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Let it be known that I have absolutely no idea how much of his family history or anyone else's fairy tale history Henry is aware of. Nor do I have a clue how old exactly anyone is on the show except for Emma and Henry (Whose ages are explicitly stated as 28 and 10, respectively, in the pilot). I've heard rumors that Snow White was 10 and Regina 18 when they met, and I'm guessing at Cora's age being somewhere around 20 when she had Regina? Idk.

If anyone can tell me if I missed something in terms of age do let me know!