Disclaimer: SN and HP belong to their creators/publishers.

Author's note and general notes about this chapter:

Um wow. It's been a while. Bare with me, I haven't abandoned this story or anything, just very slow on updates. I plan on updating Vigilante or White Stag next.

Oops! I made a mistake! concerning quidditch in the prior chapter and none of you pointed it out! This story is set in Harry's second year, but I wrote in the prior chapter that Dumbledore had postponed all Quidditch matches as he did in Harry's third year in the actual books. This is unintentional and an error on my part that I just now noticed, however, I am not going to go back and fix it. Therefore, even though Harry's only in his second year, the students are not allowed to play organized Quidditch for some reason I have yet to determine. Again oops, but hang in there, we're going to make this work.

I know Shakespeare lived in the Elizabethan Era and wrote in Elizabethan English, "which is not strictly Middle English as he lived and wrote during the transition between Middle and Early Modern English," according to our overlord Wikipedia ('cause I'm too lazy to find a more scholarly or credited source), so just bear with Dean here. The Elizabethan period spanned from 1558 - 1603 and Shakspere wrote most of his works from 1585 - 1613. Romeo and Juliet was written in 1594.

"He's going to need all of you," Bobby grunted. "I don't know what that kid's home life is like, but the lack of information the kid included about them is rather concerning. And the way that Professor acted when mentioning them… I dunno, but I think something might be wrong here."
"Maybe he will write about them later. He was told by his professors to write to us and introduce himself. Let's all be honest here, but I think we can all agree that it's Henry we want to hear about and get to know. Everyone else can come later." Sam responded from where he remained across the room.

"Well, right now is as good a time as any for you to write him a letter."
"How are we going to send it to him? Postage will cost a fortune if we're sending it to the U.K. and with all of us writing him a letter, it's probably going to be kind of heavy unless Sam can keep his letter short." Dean quipped.

"I guess send it to the return address located on the envelope," John said with doubt in his voice, but what good was a return label if it didn't work? "And don't worry about the cost of postage. I'll pay it if that means we have a chance of making it work with Henry."

Sam immediately scrambled up and began searching for a pen and pad. Dean rolled his eyes at Sam's eagerness, but in all truthfulness, he was eager to actually communicate with his youngest brother. Not that he would say such out loud.

Taking a pen and pad, he settled himself down on the couch and thought about how he'd start out his first letter to his kid brother.

Henry,

Please tell me your school uniform (don't boarding schools require a uniform?) doesn't consist of a kilt or anything close to it! You might not think anything about it now, but trust me, one day you will and you won't want the chick of your dreams to see you wearing a skirt when you show her pictures of you in your school days.

Anyway, I suppose you need to know who's letter this is and all. I'm Dean and the oldest at twenty-four, Sammy's next at nineteen meaning you're our kid brother. Great, now I have got to put up with two of you.

So your boarding school is a castle, uh, must be pretty fancy-schmancy. What do they teach over there? How to let down your hair? Who's the fairest maiden in all the land?

Don't tell me you sleep in a tower or a turret too. That would just be weird and unmanly. Not to mention straight out of a child's fairytale. Next thing you know, you'll be writing to tell us unicorns are real and that the school teaches you how to ride one.

Either way- and I am talking bro to bro, man to man here- I'd watch out if I were you, that school of yours will probably have you speaking Middle English, "O Romeo, Romeo wherefore art thou Romeo." And if you start speaking like that then you are a bigger nerd than Sam. And he actually enjoys school.

But seriously, what do they teach over there? Besides how to write with a quill pen on parchment? Tell me you at least know what a pen and a piece of paper is? I mean I am sure they teach Math and English and all that boring stuff, but what class did you have to take that taught you how to use a quill? Was it an elective, or a general requirement? And how come your school wants you to write using a quill instead of a pen or even a pencil? What happens if you misspell a word or make a mistake? Do you have to start all over?

Enough about school though, if you want to talk academics Sammy's all ears, and dad too, probably. I, on the other hand, want to know more about you and what you do when you're not hitting the books.

You mentioned in your letter that you liked to play sports, right? And that you were on the school's team. What sport do you play? They play soccer over there right? What's your position on the team? How come you were able to "land the position" when you were only in your first year? Had no one else applied for the position? Have you played any other position or are you "locked-in" for the duration of your time on the team? Why isn't the headmaster allowing you to play this year? And why aren't First Years allowed to join?

You have to admit kid, we know nothing about you, and your letter raised more questions than it answered.

So your adoptive dad was a police officer, uh? And you want to follow in his footsteps? I know your friend says it's dangerous and all, but the way I see it, kid, is if you want to do it knock yourself out.

Anyway, kid, I hope that it doesn't take as long to receive your next letter 'cause we've all been anxious for your first letter.

Your eldest brother, Dean

Smugly, Dean reread what he wrote. He felt like he covered what needed to be covered.

Glancing around he found that Sam was still working on his letter (no surprise there) but that his dad had also yet to finish writing his letter. He had figured his dad would write a rather long letter but the way the man was actually staring at the developing letter, it like it was the most important thing in the world right now and required his complete devotion.

He was probably addressing the more serious stuff, like who his relatives were, and what they were like, what the school was like, and what it was being taught over there in that fancy castle and all the other stuff that Dean hadn't really bothered putting into his letter.

Dean felt sorry for the kid once he received their letters. His hands would probably start cramping with all the writing that would be required in order to address all the questions, 'course if the kid wrote all his out-of-class assignments (it didn't count as homework if it was a boarding school right?) then he probably wasn't as prone to getting cramps like the rest of them did. Heck, the way this was going, Dean would probably be one hand short by the time the kid came home for the summer.

A few minutes later Sam finished his letter followed by John about five minutes afterward.

Dean passed his letter to Sam who in turn passed both his and Dean's letters to their dad, not before trying to peek and see what Dean had written though.

"I saw that."

Sam stuck his tongue out.

"Cut it out, both of you. I am going to see about sending these off." John said while getting out of the chair and leaving the room.
"So, what did you write to him about?" Sam asked while looking at Dean expectantly.

"I asked him if he wore a kilt, what about you? Did you ask him for beauty advice? I'm sure he would have some living in a castle and all." Dean quipped right back.

"I did not! I asked him about his friends, and what classes he was in, what his teachers were like and stuff like that."
"Nerd."

"I am not! I am just curious about the curriculum over there in Scotland. Plus it's an elite school, there's no telling what they are teaching him over there."

"That just proves you are a nerd. Because only nerds would ask about another school's curriculum. You know there is a possibility that he isn't a big old nerd like you. He mentioned that his girlfriend forced him to go to the library."

Sam rolled his eyes at his brother's antics. "So what do you think he's like?"
"I don't know. The kid didn't exactly say much other than liking sports."

"I mean, what do you think he looks like? He said he looks a lot like his adoptive father, except his eyes were like his adoptive mother's."
Dean shrugged before interlacing his fingers behind his head and kicking out his feet. "I don't know, I guess we should have asked him to include a picture or something, I mean, it's kind of weird to think we're writing to a faceless person, even if it is our kid brother."