Huge props to @avocado1322 and @DesRaven who accidentally helped me come up with this story!

Also, this is when Anne is about 15 so after the boating incident and about four years after the carrot incident.

School was almost over and Mr. Phillips was still rambling on about history

Anne liked history, she found the stories interesting, but Mr. Phillips had a way of making it bland and repetitive

Anne looked over at Diana who was also slouching down, utterly bored, and then switched to looking at Ruby who was anything but bored

Ruby was fascinated, enchanted even, but not by Mr. Phillips.

She was looking over at Gilbert with giant eyes, stopping every now and then to draw on her slate

Anne looked up a bit, slouching no longer, and saw Ruby drawing hearts around her and Gilbert's name

She smiled and shook her head at her silly little friend, Ruby was like a puppy looking at a piece of meat, practically drooling

O-o-O-o-O-o-O

After the class was excused for lunch break, Anne made her way over to Ruby who had already erased her slate and was talking to the other girls

"You're completely finished drooling over idiotic boys, huh?" Anne said teasingly

Ruby blushed, "Well, I can't just stop drooling over Gilbert, he's too handsome!"

"So tell him!" Diana said as if it were the most simple thing in the world

Ruby looked shocked at Diana, "How could I? I could never look into his eyes and tell him that I fancy him, I can't even tell him to have a good day!"

"Write a letter anonymously?" Anne suggested quietly

Ruby smiled brightly, "That's perfect!" but her smile soon turned to a giant pout, "Or would be, rather, if I could write well! This is horrid!"

Josie smirked and looked at Anne innocently, "Anne could write it since she's such an amazing writer.", Josie was still upset that Anne had beat her in the spelling bee and then had Charlie complement her, Josie didn't like Charlie Sloane, he was much too annoying and his eyes looked as if they would pop out any minute, but she thought that he liked her and had been bragging to Diana for the entire week

Anne shook her head uncomfortably, "I would rather not, it should have your words in it, not mine."

Ruby her pout extra dramatic and took a small step closer to Anne, "Oh please?"

Josie rolled her eyes, "She won't because she likes Gilbert and wants him all for herself."

Anne gasped, "That's preposterous!"

Ruby then started crying

"So write the letter."

Anne crossed her arms, "I will, then!"

Ruby stopped crying and hugged Anne tightly, "Thank you so much, remember to keep it anonymous!"

Anne then realised what she had just agreed to do, she had just agreed to writing a love-letter to her sworn enemy, Gilbert Blythe.

O-o-O-o-O-o-O

Anne looked out her bedroom window with a melancholy sigh, wishing she could be outside talking with the trees, or possibly the girls, instead of in her bedroom writing a love-letter to Gilbert Blythe, but she couldn't, she had promised to give Ruby the letter by tomorrow and therefore had to finish it today.

She didn't truly hate Gilbert Blythe, she had forgiven him after he saved her life at the pond, but she still didn't love him!

Anne looked down at her empty sheet, what could she possibly write about Gilbert that was flattering?

"I must think like Ruby does," Anne said to herself, "that is the only way to make this letter will sound real."

After what seemed like years of writing, Anne finally finished her letter to Gilbert.

O-o-O-o-O-o-O

Dearest Gilbert,

I have loved you since the day I saw you, you've enchanted me to a point of no return, lucky for me, I'm not planning on returning.

Your hazel eyes sparkle like a cozy winter day bundled up next to a fireplace, hopefully with you by my side. Your chocolatey hair looks simply pulchritudinous when you leave it unbrushed as your natural curls look like something a fairy made.

Your intellect is also something I think is very attractive, you always look so handsome standing up during the spelling bees.

I'm not sure if you've noticed me as much I've noticed you but I just couldn't hold in my love for you anymore!

As much as I would love for us to ride off into the night together, perhaps on a dashing white horse, I can't seem to gather the courage to tell you or to even write my name on this paper in the fear that you'll reject me.

So for now I shall stay,

Anonymous

Anne looked at her letter proudly, it felt real and Gilbert would certainly believe it.

She looked out of her now dark window and lay herself down in bed, blowing out her candle

O-0-O-o-O-o-O

Anne had begged to walk to school early that day, she had planned with Ruby to meet up with her early so that they could safely place the letter without being caught

"Are you sure I can do this, what if he doesn't like it?" Ruby asked anxiously

Anne dramatically gasped, "Not like my letter, how?"

Ruby smiled slightly, "I'm sure your letter is great, I'm just not sure that he'll like me."

"It's better to know now than never, if he doesn't then you can move on to someone else." Anne replied with a shrug

Ruby looked up hopefully, "I hope he does but I suppose Moody Spurgeon looks nice as well, he has awfully adorable eyes."

Anne smiled, "See, you don't have to worry!"

Ruby took a deep breath and walked into the class, placing the letter.

A few minutes later 0nce almost the entire classroom was filled Gilbert walked in

He almost immediately noticed the letter in his desk, picking it up and slowly blushing at the contents.

Ruby looked at Anne with an excited smile, "I think he liked it, thank you, Anne!"

Anne nodded humbly with a faint smile, "No problem."

After school was over, Anne and Ruby had decided to sit together and talk

Gilbert walked up to them with a slightly nervous expression and sat down in front of them both, "Hello."

Ruby beamed at him, "Hello!"

Anne simply nodded, "Gilbert."

He then pulled out a letter out of his pocket, the letter, "I just wanted to make sure this is true."

Anne smiled brightly, happy that her letter worked, "It is!"

Gilbert smiled wider than he even had before, "I never thought you could love me back, I've loved you ever since the day you smashed a slate over my head!"

Anne jumped up,Me?It's Ruby who wrote the letter!"

Ruby started crying

"Ruby? I was certain it was you, Anne! It sounded like something you would write and it's your handwriting and it even smells like you!"

"She wrote it for me!" Ruby cried through her tears

Gilbert's face turned as red as Anne's hair

Ruby then ran away

"You bastard!" Anne yelled furiously, "Ruby was so happy!"

"It was an honest mistake!" Gilbert stuttered

Anne then took off, running to Ruby's house,

Gilbert soon ran after her

Anne, panting, sat down next to Ruby who was glumly sitting with her face buried in her knees

"Gilbert is a numbskull," She angrily said in between breaths. "And I'm sorry."

"Gilbert's not a numbskull, he's perfect, but I hate him! But I love him!" Ruby pouted

Anne let out a deep sigh, "I don't understand how you like him, he's always showing off in class-"

"You do that too." Ruby interrupted

"Perhaps, but I'm actually intelligent." Anne said competitively

Ruby blushed and smiled "Oh Gilbert is very intelligent, and handsome too! I could talk about how incredible he is for hours upon hours!"

Anne groaned, "Please don't."

Just then Anne felt a tap on her shoulder, she turned around to see Gilbert waiting awkwardly behind her,

"What do you want?" Anne angrily questioned

Ruby looked up shyly, "Have you changed your mind about liking Anne instead of me?"

Gilbert smirked teasingly, "I'm afraid not, what about you, Anne?"

"You're a dunce, Gilbert." Anne responded angrily

Gilbert grabbed his chest dramatically as if he were in extreme pain, "Ouch!"

Anne held back a smile, "I'm leaving." She said angrily

"So am I" Gilbert said, following her

Anne rolled her eyes, "Well in that case, I'm staying."

"Me too." Gilbert responded

"Stop following me, you deerstalker!" Anne yelled as she ran away

Gilbert sighed and ran after her

Gilbert knew exactly where Anne would be,

He ran past the school, going into a clear-spot in the forest

The forest was extremely empty, at first glance there seemed to be no one there

There were a few daisies playfully popping out of the slightly yellow grass-filled ground but other than that no flowers seemed to be in this area

And at the far left corner there was a bushy tree, much more bushy than the rest

Gilbert gently sauntered over to the tree and shook it a couple times, "Anne?"

No one replied,

"I know you're up there!"

The forest stayed silent

Gilbert shook his head and climbed up the tree, sitting across from Anne who was staring at him coldly

"I'm really sorry, you would not believe how embarrassed I am right now, Anne."

Anne sighed, "I suppose that it would be polite of me to accept your apology, you did run after me and climb up a tree."

Anne reached out her hand, "Truce?"

Gilbert grabbed her hand with a smirk, "I was hoping for a little more than a tired old truce."

Anne raised her auburn brow, "like what?"

Gilbert blushed, "Like perhaps we could start…"

"Start?"

"Courting?" Gilbert suggested

Anne looked at her feet, "But Ruby loves you dearly, how could I?"

Gilbert held onto her hand tighter, "But if I don't love her she won't get her happy ending with me either way, what's the point of us not taking a go at it?"

Anne looked up but then quickly looked back down at her feet, "I wouldn't know how to court, I've only read about it in books."

Gilbert smiled at her, "Just act as you always would, act as you want."

Anne shook her head, "There are certain things people courting are expected to do like" Anne stopped to look up at him, "Kiss." She said quietly, "You know how to already but I have never kissed anyone!"

Gilbert chuckled a bit, "Neither have I, although I have seen people kiss."

"Never?"

Gilbert shook his head, "People have offered but I've never been interested in anyone before you."

"I don't know how to kiss." Anne repeated quietly

Gilbert leaned in to push her coppery hair out of her face, cupping her almost scarlet cheek for a moment before dragging it back down to her hand, "I think you know, Anne."

Anne got a little choked up but tried to sound normal, "And what if I don't?" She asked, leaning in even more

"I might just have to show you." he said teasingly, leaning in until there were only about two inches between them,

Anne changed that to one, "Please do demonstrate."

And soon enough there were no inches between them

Ruby ran over to the tree, she was very late as Anne and Gilbert were both fast runners

Not fast enough, however,

Ruby had reached the tree at the part where Anne started talking about kissing, she listened in from there on

Ruby was infuriated at first, hitting trees nearby, but then turned sad, lightly crying under the tree

Anne pulled away once she heard light crying, neither of them noticing the sound of trees being assaulted, "Ruby?" She called out with fear

"Yes, why don't you and Gilbert come down?" Ruby responded

Anne looked nervously into Gilbert's eyes, Gilbert's only response being a quick head nod and squeezing her hand

They both climbed down cautiously,

"How could you do that to me? I trusted you, Anne!"

Anne looked down at her feet with a guilty expression "I-uh."

Gilbert spoke up, "I like Anne, Ruby, and I asked her to court, she tried to say no for you but I convinced her to do otherwise, if you want to blame anyone, blame me."

After a moment of silence Anne spoke shakily, "Why aren't you crying anymore?"

Ruby smirked, "I like Moody now."

Anne rolled her eyes, "Already?"

Ruby nodded, "I'm going to go home, why don't you two talk?"

"Why don't we?" Anne said, turning to Gilbert

Gilbert gave a boyish smile but his face soon turned serious, "We are at the right age, Anne, but would Matthew and Marilla approve?"

Anne raised her auburn brow, "Matthew and Marilla love you!"

"Well, that's awfully convenient." Gilbert said teasingly, "Lets go ask now!"

"Wait!" Anne said,

Gilbert turned around, "What?"

"You never asked me!"

"We just kissed and you said you loved me." Gilbert said, raising his brow

"But you never formally asked!" Anne pouted

Gilbert chuckled, "Anne-with-an-E Cordelia Shirley-Cuthbert, do you agree to court?"

Anne giggled, "Yes."

So they walked to the Cuthberts' house, asking for approval to court

And that was Gilbert's second "Yes" of the day

Before Gilbert left to go home, Anne stopped him on the doorstep, "Can you believe that this all started with a letter?"