Author's Note: Inspiration from a Calendiles AU that I'm kind of halfway working on, and a little from DragonyPhoenix's The Letters, which is entirely unrelated to this but still very good.
To: rgiles
From: jcalendar
Subject: Change your email password, Rupert
I could easily log into your account and send an email to myself detailing all of the things you love about me. It could get very flowery. I will remind you that these are SCHOOL ACCOUNTS and if the administrator so chose, they could send the email on to Snyder.
Rupert, you're adorable, but you're going to get hacked. I set up your email for you last year and you still haven't changed the password to something non-generic. Trust me. You're going to want to change it soon. I have a plan requiring the use of your email address that I know you won't appreciate.
Jenny
To: rgiles
From: jcalendar
Subject: Rupert…
I just tried logging into your account and it still worked. You don't even have the excuse about not knowing that I want you to do this, because I stopped by your office and told you in person. And I know you remember that.
Jenny
To: rgiles
From: jcalendar
Subject: GET ONLINE SOON OR I SWEAR I'LL GO THROUGH WITH IT
[no message]
Bcc: rsnyder
From: rgiles
Hello all!
This is Mr. Rupert Giles speaking. I'm so terribly sorry that I wasn't as friendly as I would have liked to be last year; my beloved Aunt Ethel died and I took it very hard. To make up for this, I'd like to volunteer the library for the location of the next faculty meeting. I shall be providing snacks.
Cheerio!
Mr. Rupert Giles
To: jcalendar
From: rgiles
Subject: Never do that again
Thanks to you, I'm fielding awkward questions about my nonexistent Aunt Ethel. I think I told someone that she died because someone kept on asking her irritating questions. It may have been a student. I am quite on edge.
And also, I've never said cheerio in my life.
Rupert
To: rgiles
From: jcalendar
Subject: The cheerio was very necessary
Everyone on the staff is convinced that you speak like that since I'm the only person you talk to. You need to make more friends. Plus, I did say that if you didn't change your password, there was a possibility of you getting hacked. You're lucky it was me. I was nice.
To: jcalendar
From: rgiles
Subject: Nice?
Hardly.
Rupert
To: rgiles
From: jcalendar
Subject: Ok, maybe not nice…
…but I'm sure you're not averse to some naughtiness here and there ;) Up for some this Saturday?
Jenny
To: jcalendar
From: rgiles
Subject: Didn't you say these were school accounts?
Can't Snyder see these emails?
Rupert
To: rgiles
From: jcalendar
Subject: You're a dork
He can only see them if the administrator deems them inappropriate in the workplace and sends them on to him. The administrator happens to be this really awesome computer science teacher, and from what I know of her, she's cool with it.
Jenny
To: rgiles
From: jcalendar
Subject: To put it bluntly…
I'd like you to come to my place Saturday night. Don't plan to go home until Sunday afternoon.
Jenny
To: jcalendar
From: rgiles
Subject: I've checked my prophecy books
No impending apocalypses. I'll cook us dinner.
Rupert
Postscript: I did change my email password. And I don't have to host any more staff meetings anymore, because the one in the library went so abysmally, so I do have you to thank for that.
To: rgiles
From: jcalendar
Subject: FINALLY!
[no message]