To Win a Mare's Heart

by Master Lyra

Rating: everyone
Tags: Slice of Life, Comedy, Romance
Length: 1105

When Big Mac finds out Caramel has the same feelings he does for Fluttershy, chaos breaks loose.

Big Macintosh is a socially discontent indivdual. Every weekend he works, goes to the bar, and hangs out with his select group of friends. But when one of his friends confesses his love for someone near to Big Macintosh's heart, he takes action. He has to win her heart before his friend does. But you can't judge a book by its cover, and nothing is as simple as it sounds…
Cover art by tateshaw.

Published 1970-01-01 00:00:00 UTC
Last updated 2012-07-19 20:44:02 UTC

Chapter One: The Squeezed Lemon

Dear Diary,

When I was younger, I was an active soul. I worked day in and day out to take care of my beloved Sweet Apple Acres, planting seeds, plowing farmland. I wasn’t very active in other ways, though. Socially, I was inept. But, from the other entries in this diary you might know that. I’ve grown accustomed to this lifestyle, admittedly. I like it. It makes life simpler, and it leaves out drama I would have to experience otherwise.

But diary, please tell me; why does all the drama have to start now?

I used to not even think of “hanging” out with ponies. It made me uncomfortable. Why is it that now I have all these things to juggle? I can’t confess my feelings to Fluttershy, and Caramel has already started in on the kill! How can I compete with Caramel? He’s the slickest, trickiest stallion in Equestria! Plus, he’s backed up by the fact he’s won a mare’s heart before! I wish I had someone who could help me sort this all out… hmm… maybe Rarity?

             -Big Macintosh.

[3 HOURS BEFORE]

“…and then I banged Derpy… UPSIDE-DOWN!”

A whole table of blank faces met Caramel’s story.

“…”

“Aww, c’mon! It was LEGENDARY!”

“You’re disgusting Caramel.” Rarity said, giving him an equally disgusted face.

“She’s right Caramel. It’s those kinds of stories you keep to yourself. Anyway, Rarity, I have to go take care of Spike. He… can’t handle being alone that long, as you know. “

Rarity shuddered, but nodded.

“I’ll see you there.”

I sat silently, just listening to the entire bar. The Squeezed Lemon. This was the place I went to every day, every night, the same time. I knew this place; it seemed, as well as my own barn. Ever since a month ago when I started coming here alone, I had learned about all the ponies here and their personalities. You can learn a lot by just listening. And ever since Caramel noticed me sitting by myself, he invited me over. The group, well, is pretty much no different with me here. I mostly just listen to their interesting lives. Rarity and Twilight’s struggling relationship, Caramel’s… interesting adventures, and Fluttershy’s meek additions. If there’s anything I’ve learned by living in Ponyville, it’s that word travels fast. That’s why I don’t talk much.

“Mac, you alright?”

I looked at Caramel, who had probably been looking at me for some time.

“Ah’m fine.” I announce with the little grace I can with my Apple accent.

“Good. Anyway, I was in a candy shop and…”

I’ve learned how to tune out most of Caramel’s stories. Not to speak bad about him, but, they usually end up with him… in bed with a mare, so why bother listen to how it happens? Caramel is an interesting character. I hired him a couple months back to help on the farm when Applejack injured her hind legs and couldn’t buck the apple trees. He is a strong worker, but sometimes he can be… what’s the word… egotistical? He can be very full of himself at times. But it you look past that skin of engorgement… he’s a good pony deep down. He’s definitely a shoulder t lean on when-

“Mac? Mac, you seriously alright? You’ve just been sitting there with a blank face for ten minutes.”

“Ah told ya, Ah’m fine!”

“Alright, alright! Jeez… anyway, I swear, that mare had a candy flank…”

*sigh*

“Is it really that bad Mac?”

Whoops, I must have actually sighed.

“Nah, Ah’m just thinkin’ ‘bout all of us, y’know, th’ group.”

“Ah, well, while you were daydreaming, Rarity left to go to Twilight’s. Having a sleepover or something, but we all know what they’re actually going to do…”

I drank half of my cider at the thought.

Fluttershy, who hadn’t said much, or anything really, stood up with a queasy look on her face.

“I… I feel sick…”

She bolted to the bathroom with such a speed that would make Rainbow Dash jealous.

Caramel looked at the dust trail of Fluttershy, swiveling his glass.

“Y’know, she’s a good gal but she can’t take my stories, can she?”

I sighed as I looked Caramel in the eyes.

“Ah wouldn’t blame her Caramel.”

Caramel gulped down a shot.

“Eh.”

His eyes glazed over as he took a long look in the direction of the mare’s bathroom.

“Mac… I think I might have something for that mare…”

I didn’t think I heard that right.

“Pardon?”

“I think I might be… falling in love with Fluttershy.”

Ah, Fluttershy. The mare of everyone’s dreams. She’s swooned many, however accepted none. Why is a mystery to me, but to each to their own I suppose. It used to be just Fluttershy and Rarity hanging out together, but soon they met Caramel, back when he wasn’t much of a pony. They brought him out of his shell, and he was never the same. Then, Rarity and Twilight found each other to have more than just friend feelings for themselves, and hooked up. The rest, is well, history.

Back to Fluttershy.

Caramel has all rights to like her I suppose. They’ve known each other for a lot longer than me. Plus, he already has an emotional attachment to her, form when he was… new and all.

Hm. Maybe I like her too…

Nah. I don’t… do I?

Well, she and I have a lot in common. I’m shy, she’s shy, I’m socially inept, and she’s socially inept. She’s never had a coltfriend, I’ve… well, of course not a coltfriend, but the point still stands.

I’ve never had a marefriend.

Well, I guess I’ve never had the desire or temptation to. I’ve always preferred hard work over lovey-dovey things. It gives you time to think, and brings food to the table. Not to say that people who do focus on their social lives are… idiotic, but I think that if they focused on making a living, things are simpler and easier. However, now that I have to think about this, personally…

“Hmm… y’know, I might just go and ask Twilight for help tomorrow.”

Huh?

“She’s the one who confessed her love to Rarity, so I think she’ll help me with Fluttershy…”

“Ah don’t know about that, Caramel. Are ya sure that ya like her?”

“Eeyup.”

Did he just… mock me?

…

Oh it’s on now.

“Alright, Caramel. You should go fer her then.”

“Thanks Mac.”

Hehehehe… I can beat him to it, can’t I? I'm gonna win her over first.

Wait, what have I just gotten myself into?!