Hindsight
by Jack of a Few Trades
Words read: Completed Story

Poor Miss Cheerilee. That mare gets as bad a rap as any background pony I can think of in pony fiction. Being associated with one of the most famous anti-shippings in the fandom has left her being portrayed as depressed, isolated, occasionally even insane and abusive. She's even been portrayed as one of the internet's most infamous practitioners of genocide... and accordion playing.

Yes, someone actually drew that. You're welcome.

At least we have Jack of All Trades, a reviewer here on PCaRG, to tackle the underlying issue with the character instead of turning her into a Serbian Ustaše. Hindsight is here to once and for all sort out this mare's emotional baggage so we can move on and talk about all the suitors she had back in the 80's. Turns out the gal had no problem at all finding a dude until after she agreed to Lauren Faust's "No Shipping" clause. Fire your agent, sister!

The story starts with a fairly basic description of Cheerilee waiting for her food at the counter of Sugarcube Corner.

Ting!

Cheerilee tapped the bell on the front counter of Sugarcube Corner for a third time, craning her neck to try and see into the back room for some sign of activity. She could hear Pinkie Pie chattering away somewhere back there, but she didn’t seem to be hearing the bell.

“Hello?” Cheerilee called towards the back room.

A bit of commotion on the order of a pot falling to the floor and a shout from Mr. Cake signalled that they had probably taken note of their waiting customer. A second later, the swinging doors to the kitchen blasted open as Pinkie herself came bounding out to the front room with a bit of flour in her mane and a stained apron hanging from her neck but not attached around her barrel.

“Hiya, Cheerilee! Sorry about that; I didn’t hear you out here.” Pinkie punctuated her sentence with a giggle as she crossed to the counter.

“It’s fine, Pinkie. I understand things can be busy.”

“I know, I know! Things have been crazy without Mrs. Cake here to help. Me and Mr. Cake have been chasing our tails all day!”

“Oh really? Where is she today?” asked Cheerilee.

“She had to take the twins to the doctor to get their shots. She shoulda been back two hours ago!”

“I’m sure they’re just stuck in the waiting room,” Cheerilee offered. Her smile faltering slightly as she took a closer look at Pinkie. There were noticeable lines around her eyes, and her mane was a bit more frazzled than usual.

“Yeah, I hope so. You’re here for that big cupcake order, right?”

“Yes I am. Is it all ready to go?”

“Yep-aroonie! I’ll go and get that for you.” Pinkie turned face and raced back into the kitchen.

This story is on a mission and not going to waste time on overly elaborate descriptions. I actually appreciate this given the fact we tune in and see these locations on the show all the time. There's a lot to be said for hustling through set-up scenes like this to get to the plot, which emerges a few, short paragraphs later:

The first thing she noticed was the return of Pinkie’s chatter coming from the back room. She turned her head and cocked an ear towards the doorway, trying to focus on what was being said.

“...the boulder took forever to push back up that hill! I almost pulled a muscle in my back from that. Can you believe it?” said Pinkie.

Was it wrong to eavesdrop on them? After all, she might wind up hearing about something she really didn't want or need to know.

A well-timed growl from her stomach told Cheerilee to keep listening to forget about that tantalizing chocolate cake with the chocolate mousse layers and chocolate shavings sprinkled on top…

No, no, no! Focus on the eavesdropping!

“...got the boulder up the hill, we were all reeeaaally really tired, so we all went in the house and rested for a while.”

“So I take it that you all got along well after that?” asked Mr. Cake.

“Things went super-duper after that! Ma and Pa really started hitting it off with Granny Smith, and I think my sister Marble Pie finally found herself a stallion!”

“What do you mean?”

“Well, she and Big Mac kept looking at each other and hanging out a lot after that...”

Wait a second…

Big Macintosh was getting a crush on Pinkie Pie’s sister?

“...while Maud was singing her Hearth’s Warming carols, I noticed two certain someponies leaning up against each other! It was sooooo cute!”

So, Big Mac had a special somepony now?

Basically this story is the part three and finale to the story which started with season two's "Hearts and Hooves Day" and followed up with season five's "Hearthbreakers", which introduced us to Marble Pie. The latter pretty much destroyed HMS Cheerimac, sending her to a watery grave and leaving the survivors to be consumed by sharks in the South Pacific. I'm not really sold on the idea that there's anything more to be said, given the lack of any sexualization granted to the Cheerilee character by the writers. It really does seem like Cheerilee found the idea of her and Bic Mac to be silly at the end of Hearts and Hooves and there's no reason to question it. Not that that will stop this story from trying! Take it away, Jack:

Cheerilee watched the children begin to socialize amongst themselves, the different friend groups forming up in different corners of the room. Twist, Featherweight, Pipsqueak, and Truffle Shuffle were near the front of the class, and the Cutie Mark Crusaders and Diamond Tiara were along the far wall. The fact that Diamond was no longer antagonizing the trio was going to take some getting used to. Still, it was what it was, and it seemed that Diamond was getting along with Apple Bloom the best out of the three.

I wonder what Apple Bloom knows about Marble Pie.

Cheerilee blinked in surprise and scrunched her muzzle at her own thoughts. Why in Equestria would seeing Apple Bloom and Diamond Tiara being friends trigger that whole chain of thinking?

Uhh, because he's her sister? This isn't unusual.

“Is there anything to drink?”

“Oh, yes. Of course.” Cheerilee stood up to address the class at large. “Would anypony like some milk?”

The party ended with the final bell, and the students all said their thanks as they frantically put on their winter gear and left for the day in their usual stampede. The room was empty, save for Cheerilee, and she too was preparing to leave.

Now this is a bit more unusual. There's two lines of empty space where a horizontal rule usually goes.

Only two more months until Winter Wrap Up. You can make it, Cheerilee. She crossed the small bridge over one of the town’s creeks, taking care not to slip on the ice on the bridge. Cheerilee picked up a steady lope after she crossed the bridge and took a moment to admire the town’s scenery. Ponies were out and about today, enjoying the very minor relief of the slightly less chilly day to go out and run errands. A few buildings were still decorated from the holiday season, and coupled with the snow on the roofs made them look reminiscent of gingerbread houses at Hearth’s Warming.

Big Macintosh and Marble Pie probably enjoyed themselves at Hearth’s Warming.

I skipped over an instance or two where Cheerilee has this distraction bit occur. It's obvious from the start that this poor girl has got it bad and needs to talk about it. For me, being an adult, this was dry reading up to the obvious outcome and seemed to go on a tad bit too long. For younger readers who still retain some mystery about the universe, this is perfectly fine though. The story is marked E for everyone, so it's less a criticism and more an observation from a jaded reader.

Cheerilee does eventually find an obscure background pony character named Nook in chapter three to discuss her problem with and we get some new information to fill in the blanks left by the canon.

“Big Mac?”

“E’yup?”

Cheerilee hesitated for a moment, looking up at Mac. She tapped his hoof, getting him to look her in the eye.

“I think we need to talk about a few things.”

“E’yup.”

Cheerilee stopped, trying to find the right words. “Oh Celestia, this is a little harder than I thought it would be.”

“E’yup.”

“I, uh… Big Mac, as funny as this sounds, we need to talk about us.”

Cheerilee waited for a response from Big Mac, but he remained silent. He broke eye contact and instead returned his gaze to the sunset. Cheerilee frowned; surely he knew that they needed to talk about this subject. She was about to tap his hoof again before he finally broke the silence.

“Miss Cheerilee, I don’t know what to do. I’ve been thinking a lot after we woke up in the pit, and I just keep getting all mixed up.” Big Mac paused, taking a deep breath before he looked Cheerilee directly in the eyes again. “I figure this’ll come out soon enough anyway, so I’ll be honest with you. I think you’re right pretty as a mare can be. You’re sweet, great with the kids, and I realized this afternoon that I enjoy being around you.”

He looked away again. “But when I start thinking about if you’d want to start a real relationship with me, it scares me. I can’t help feeling like that potion might still be making me crazy when I think about you like that. How’d I know if I’m thinking right?”

Cheerilee sat there and looked out into orchard.The sun was more than halfway across the horizon now, and the entire area was beginning to lose the light. The darker colors of the sunset painted the trees in the orange hues of fall as time kept slipping further and further away from the two

Two things come to mind as I read this: First, the last paragraph needs editing; and second, this problem can easily be solved by talking to Big Mac. He's the guy holding all the cards here. Talking to other people is not a bad way of dealing with problems, people do it all the time. But we haven't learned anything new here that changes our current level of understanding. A thing happened and ponies are confused about it. A few paragraphs later and the obscure background pony basically says what I just did, adding that there's no way of even knowing if Mac and Marble are even an item. I guess sometimes we need to hear it from other people because we're too close to the thing that's giving us grief. It is called "Hindsight" after all. Armed with this knowledge, Cheerilee vowes to not talk about her problem, and eats cake instead. Here we get the most obvious of all obvious cues that Cheerilee has got it bad.

The memory faded, and Cheerilee blinked, finding herself staring at that same door. A part of her wished that Big Mac was still in that bathroom, gathering up his tools, there so she could just tell him how she felt and get it all over with.

As far as stallions go, he sure is something special. How many boys around town would spend an entire Saturday afternoon helping me fix up a sticking bathroom door? Cheerilee broke her stare from the bathroom and shifted it to the closet that was the second door down the short path towards the guest bedroom.

Something special was stashed in there.

She opened the closet, pulling a small folding step stool out and opening it up. She climbed the step, reaching up to the top shelf. She pulled a box down, taking care to not jostle it as she set it on the floor. She lifted the lid and there on the very top, laid carefully over a bed of books purchased from Princess Twilight herself, was the wedding veil she had worn on Hearts and Hooves Day. She picked up the delicate piece of fabric, letting it drape over one hoof as she caressed the beautifully intricate, personalized designs that only a seamstress of Rarity’s caliber could make on such short order.

Would I have kept this if I didn’t feel something for Big Mac deep down?

NO! Go talk to him, you fool!

Cheerilee blinked, and she nearly dropped the veil as she realized where her thoughts were leading. Am I... falling in love with Big Macintosh?

Falling in love? Sounds like you were already on board with this thing back in season 2. What was it that made you fall in love exactly? Finding out that he was taken— Ohh! You know, I bet that was it!

An aside before I continue talking about the story. You remember how back when you were a single man and no woman wanted anything to do with you? Felt like crap, huh? Then you went out and actually convinced some woman to let you give her jewelry and live in that dump of a place you got? Suddenly your house is much nicer looking and women are all paying attention to you. This story is teaching us a valuable lesson about sexual marketplace value; a guy who can attract a woman will attract more women. This is because women want the absolute best provider for themselves — and aren't ashamed to have you after another woman, I should note — and getting another woman's endorsement for a mate is a valuable indicator of status. It works a lot like credit: you can't borrow money unless someone else is willing to give you a loan. If you're one of those guys still living in the dirty house/apartment, consider a shotgun method to getting a girlfriend. No, don't approach them with firearms you psycho! We don't need to hear about another case of the Eternal Gentleman on the news. Just ask a bunch of them out until one says yes. Once you're in, start networking with her friends and her friends' friends. But AJA, it can't be that easy! No, it really is that easy. Stop being miserable about women online; we've heard about it. Rant over. Back to the story:

Finally deciding to go through with talking to Big Mac, Cheerilee meets Apple Bloom walking around the country path leading to Sweet Apple Acres. After asking the little filly about her trip to the Pie Family Rock Farm we get a short recap of "Hearthbreakers" that goes on for slightly too long. I don't think it'd bother me if we got insider details we didn't get on screen, or it stuck to referencing one specific event like the rock soup, but it just felt like cheating to me.

“So,” Cheerilee said, trying to keep the conversation going. “I don’t think I ever asked you. How was your Hearth’s Warming?”

Apple Bloom’s face lit up a bit. “It was interesting for sure, but I had a lot of fun!”

“Oh? How was it interesting?”

“We went with Pinkie Pie to celebrate Hearth’s Warming with her family, and let’s just say that they have some funny traditions.” Apple Bloom rolled her eyes. “They eat rock soup for their feast, they only decorate by covering the place in crystals, and they hide their presents from each other and search for them. Usually they hide them so good that nopony ever finds them.”

“Rock soup?” Cheerilee asked.

“It’s exactly what it sounds like,” answered Apple Bloom, her voice deadpan. She mimed gagging to accentuate it.

“Wow, maybe that’s why Pinkie’s the way she is.”

“Actually, no,” said Apple Bloom. “Pinkie’s probably more different from them than we are. They’re all kinda… what’s the word?”

“Bland?” Cheerilee suggested. It was one of the few antonyms for Pinkie Pie she could think of.

“I guess that works. It was a little disappointing at first, but I got to having fun doing something different.” Apple Bloom paused for a second before she grimaced. “Applejack wasn’t so easy to come around though. She tried to completely change all of the Pie family’s stuff into regular Hearth’s Warming stuff. I still don’t know where she got all of those decorations, but she nearly got us kicked out of their house.

“What happened?” Cheerilee asked.

“We left for a little while and then went back to apologize, and then we got everything going again. We might do something like that again next year, but I want to do it the normal way next time!” Apple Bloom grinned.

Unnecessary addition or valid scene building? You make the call.

Cheerilee does eventually meet up with Big Mac and we get a nice fake-out where it looks like she's going to chicken out and tack on yet another chapter to the story, but in the end Big Mac gives her a no after a pretty touching exchange. The feels are real. Nice work!

I'll leave the final chapter unexplained. For me the story ended on chapter four with the lesson that people should just talk out their issues. Cheerilee punished herself for three full chapters and was miserable and ended up eating cake. But once she got up the nerve to talk about it she was still miserable because she got shut down... but she wasn't curious anymore. That's a fine life-lesson if I ever heard one!

All in all the story was enjoyable, but there were a noticable few typos scattered across it — particularly towards the end. Another editing pass to clean those up would be a good idea. The story is alright, if pitched for a younger audience than me.

Now go out there and ask out those women or else the big, bad alpha males will grab them all.

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This story is teaching us a valuable lesson about sexual marketplace value;

Son, this ain't a can of worms you really want to open.

We do have female members of the group, and they might object to being analyzed as if they were economics-driven robots.

And personally, I think that effect has more to do with the man's confidence than the woman needing proof of his ability to attract a mate like they're chimpanzees or something. Once the previously-forever-alone guy is in a relationship, there tend to be two changes in him. First, he now knows he can attract someone, easing doubts through his knowledge of his own success. Second, he no longer needs to actively seek someone out — and in my experience, guys who lack self-confidence but are trying to land a relationship come off as off-puttingly desperate.

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This is because women want the absolute best provider for themselves — and aren't ashamed to have you after another woman, I should note — and getting another woman's endorsement for a mate is a valuable indicator of status.

*twitch*

Once you're in, start networking with her friends and her friends' friends.

*double twitch*

And once you do that, you've just poisoned an entire group of women against you once they figure out you were simply using their friend as a way to get to the rest of them.

Don't do this.

We're people. We want to be treated as people. Not as enemies, or playing pieces, or obstacles to be conquered. We want a guy who is confident in himself (for the most part: some gals like projects) and we want a guy who is going to treat us like a person (again, for the most part, you do have golddiggers and trophy wives for a reason).

Rinnaul hit the nail on the head: a guy who was previously single and is now getting all the attention after dating is getting the attention because he's confident. And you can find other ways to confidence besides desperately asking every girl possible for a date or making sure you've gotten to know all of your current SO's friends to guarantee you have a fall back.

Approach us like you want to get to know us as a person, not as something to be scored, won, or whatever, and you're going to have a much nicer time.

And this:

Now go out there and ask out those women or else the big, bad alpha males will grab them all.

Alpha males don't exist. It's a complete trope construct from Romance.

/rant

On the review, pretty decent. I would've liked to have seen more analysis and reaction on your part and less quoting from the story, but that's personal preference.