A/N: My first ever OUAT fic, so sorry if I get some stuff wrong. Anyway, tell me you guys have thought about this too…
Henry knocked on the door, fidgeting a little with his heavy backpack. There were probably half a dozen other people he could've asked for help, but he hadn't thought of them up until the moment where he found himself in front of the intricately designed door. Besides, this project was due in 2 days and he didn't really feel like leaving just to look for someone else. Yep, it was too late to turn back now. Or maybe this was a bad idea…
Just as Henry turned to leave, the door opened and out stepped a man with ruffled dark hair and eyes that seemed to have a glint of crazy somewhere behind them. He regarded the boy carrying a too heavy pack with a small eye roll and leaned onto the door frame.
"Is there something you need, Henry?"
"Did Grace tell you about this family tree project that we have to do? It was assigned, like, three weeks ago, but I haven't exactly done any of it?" Henry pulled out the direction sheet and thrust it into Jefferson's hands.
"Uhh, she did. In fact, she finished that last week. Is there any particular reason you're at my door and not, oh, I don't know, working on the assignment?"
"I need help! Maybe you haven't noticed, but my family isn't the easiest thing to map and you're my last hope. Please help me."
Jefferson sighed, but opened his door to let the boy in. "Just so you know, Grace is at a friend's house, so it'll just be us… Are your parents or grandparents or whatever gonna be ok with that? They don't think I'll murder you or anything?"
"Yeah, yeah. They already know I'm here," Henry waved off the question. "Let's get started, I don't want to take up too much of your time."
"Well, you kind of are… There really wasn't anyone else in the entire town you could've asked first?"
Henry got out his supplies and spilled them onto the coffee table. "My mom and David are fixing the whole ice and Snow Queen situation. Mary Margaret and Belle are busy with baby Neal, or the shop, or taking care of the town. I have no idea where Hook even goes in his spare time or if he even lives anywhere, and I was already halfway here before anyone else popped up in my head."
"What about Regina?" Jefferson asked, even as he succumbed to his fate to help this kid with his gigantic family. "Or even Rumplestiltskin? Do you want some tea, by the way?"
"My other mom is in her vault, trying to solve a whole 'nother ice situation. And I'm supposed to be working for Mr. Gold, not asking him for help on homework. Plus, I feel like he'll trick me into making some sort of deal to get the project done quicker. And no thanks to the tea." Henry spread out a large piece of construction paper on the floor. "So, you see, you're kind of all I've got left."
"All right, fine." Jefferson sat down on the floor near the paper, sipping a cup of tea. "Tell me what you need, because with the size of your family, we're gonna be stuck here for a while."
Henry took out a black marker and wrote his name down at the bottom, drawing two branches upward. "Let's start off with Emma and Neal…"
An hour later, the tree was nearly finished, ending at King Henry, Regina's father. Jefferson suggested finding out his parents, since going past 3 generations would get him some extra credit points. Henry decided against it, mostly because that would've required more research and that was too much work at this point.
"How do you know so much about my family anyway?" Henry asked, handing Jefferson a pen to write a giant cursive F and T at the top.
"Well, you hear things when you go around as I once did. I was a traveler, kid, and that meant meeting all kinds of people." Jefferson hedged, finishing his F with a grand flourish. "And making all kinds of connections… and enemies. But, you know, occupational hazard."
The poster looked… amazing. Plus, Jefferson's calligraphy as part of the title made it look that much more sophisticated. The only problem that faced them now was the explanation Henry had to provide to summarize the tree.
"Ok, wait, so Peter Pan…err… I mean, Malcolm was Rumplestiltskin's father, we have that down." Jefferson pointed to the very top of the tree, tracing the line down to Neal. "And Rumple is Neal's father and Neal's mother is some lady named Milah."
"Right…" Henry capped his pen and sat back to look at his written response.
"So where does Captain Hook fit into all of this?"
"Hook fell in love with Milah and she ran away with him, so that basically means he is Neal's stepfather…right?"
"Let's just say yes, who's gonna check? But then why did you connect Hook back to Emma?"
"I used a green line, which means they're dating. See, I did the same with Regina. But, she has a broken green line with Robin Hood. They were dating, but kinda hit a rough patch when Robin's dead wife came back."
"Ok… Look, I just think you're going way too far with these branches." Jefferson poured himself and Henry another cup of (cold) tea, who finally accepted one about 30 minutes into the project. "And since when are you so interested in your moms' love lives?"
"Are you kidding me? They're always busy with something. I mean, I get it. So, getting involved with their love lives is the only way I can ever spend any real time with them. And their boyfriends. If it has to be spent playing matchmaker, I'll take it." Henry admitted, sighing heavily at the memory of all the work he's put in with his moms.
"And I'm just being thorough. What if Regina and Robin fall back in love and get married or something? What if Emma and Killian suddenly decide to get married?"
"In the next two days? I highly doubt that…"
"Yeah, but this way I already have their photos on the paper."
Jefferson suddenly let out a loud laugh, spilling a bit of tea onto his carpet. "Oh god, can you just imagine your mother and Captain Hook getting married? He would be both your stepfather and step grandfather! Wow, I never really realized how messed up your family history really is."
"Ok, technically, Killian was never my step grandfather. He and Milah didn't elope or anything. But I see your point. My grandparents are only, like, less than 10 years younger than my mother. And there's my great grandfather who was most likely around 18 when we met."
"I still can't believe that you were technically your own great grandfather when Peter Pan was in your body!" Jefferson paused for a moment, considering what he just said. "What kind of a life do you lead where a sentence like that doesn't even slightly throw you off?"
"Yeah, you're telling me." Henry took a gulp of tea from his cup. "I better get the best grade of my life on this project!"
He and Jefferson burst out laughing. "Then we better make sure make sure this essay length summary of yours is top-notch!"
A half hour or so later, the explanation looked like it fit the tree pretty well. It was as good as it was going to get, anyway, without completely confusing Henry himself.
"So let me walk you through this. I'll just go with their Storybrooke names to make it easier on the both of us. And that's how I wrote it on the page, so..." Henry adjusted the poster so it was facing Jefferson directly. "It starts with King Henry and Cora, my adoptive grandparents. Their daughter is Regina, my adoptive mother. Regina also became my maternal grandmother's step mother when she married Mary Margaret's father, whatever his name was. Then Mary Margaret married David and they gave birth to Emma. On my dad's side, it starts with Malcolm/Peter Pan. His son is Mr. Gold and his wife was Milah. They gave birth to Neal, who spent however many years as a kid, because he was at Neverland. And that's where he met Killian, who was supposed to be his step father. But Milah was already dead then, so that didn't happen. Then Neal left and met Emma in New York, where they had me. Now, recently, we found out Zelena, or the wicked witch, is also my adoptive aunt. I'm not too clear where that falls in the order of things. Oh, and Belle and Mr. Gold are now married, so she's also my grandmother."
"Step-grandmother," Jefferson corrected.
"Right. I think that about sums it up. What do you think?"
Jefferson sipped his tea and put his chin in his hands. "I'll be honest, you lost me before you even got to Neverland."
"Jefferson!"
"I'm sorry! I was mixed up. Now, what about me?"
"What about you?" Henry gave him a look of confusion mixed with horror at the thought of another unknown relative.
"Oh, sorry. At this point, I assumed you were related to, like, the entire town and you were just gonna put them all on there. "
"Jefferson, it's not funny! This is due in less than 48 hours!"
"Whoa, calm down. We're done, aren't we?" Jefferson picked up the poster and held it up towards the light. "The only thing you're missing is baby Neal. You're an uncle now, Henry. Announce it to the world!"
"Pretty sure they already know. I mean, there's not much about the Charming family that people don't know. Anyway, thank you so much for putting up with this. You are a lifesaver."
"Oh, it was hardly a problem." Jefferson gloated, as he got up to walk Henry out. "And, hey, my door's always open. Tell me how the project works out."
"'Course. Thanks again, Mad Hatter."
A week or so later
"Can you help me write a fractured fairy tale?"
Jefferson smiled at the boy's frantic expression. "Should be easy enough. I mean, it's basically your life." He swung his door open wider, ruffling Henry's hair as he walked in.
"By the way, did I mention I have to turn this in online before midnight?"
"How do you even find time to go to school?!"
A/N: I didn't bother mentioning all of his grandparents cuz that'd be toooo much.