“We refuse to accept this money.”
“...Why?”
“We know better than to accept bits from the Rich family. There’s no telling where those funds came from.”
“Excuse me?!” Diamond Tiara, the newest head of the Rich family, rests a hoof on her chest in shock. “Putting aside the fact that such claims are slanderous, this is a charity! Who are you to deny a donation?!”
“The founder of the charity in question. Now, if it’s all the same, I’m going to have to ask you to leave.”
“But… but…!” Closing her eyes, Diamond Tiara scrunches up her nose and stifles a grunt of frustration. Her face visibly gets redder for a moment as she attempts to control herself, but the color begins returning to her face as she literally bites her tongue and takes a deep breath. “Very well. I shall inquire elsewhere.” She bows lightly, trying her hardest to not seem sarcastic. “Good day to you, sir.”
Attempting to hide a huff, she quickly turns around and marches out of the small, humble building without daring to look back. She briefly hears the middle-aged stallion click his tongue just before the door closes behind her, and it takes everything in her power to not march right back inside.
Such is the life of Diamond Tiara, daughter of Filthy and Spoiled Rich and sole heir to the Rich family fortune.
As she steps out into the midday sun, she closes her eyes and takes a moment to just let the summer heat wash over her. It’s a relatively quiet day in Ponyville, with the distant sounds of children playing and voices from the nearby market making the town feel alive.
A cool breeze washes over her, causing her perfectly curled mane and tail to gently sway back and forth. With a sigh, she adjusts her namesake which rests atop her head. This is her way of meditating, something she has been practicing a lot lately.
Every day, it feels as though she walks along a razor’s edge. On one hoof, she is adept at getting ponies to do what she wants. It’s what her cutie mark is all about, after all. On top of that, she’s inherited her family’s fortune and business, giving her ample opportunity to grow and experiment. From the outside looking in, one might think she has everything she could ever want.
However, on the other hoof, she has to deal with what those privileges bring. Somewhat ironically, being known as a pony good at getting others to do what you want makes ponies distrustful of you and unwilling to speak to you at all.
Meanwhile, when Princess Twilight Sparkle took the throne from Princess Celestia, Diamond’s father got mixed up in some shady business and exploited a poorly worded tax law. He technically didn’t do anything wrong, and he certainly came out richer for it, but said business quickly became known to the public. He avoided jail and kept his wealth, but his reputation was in shambles.
This situation would come to be known as the “Canterlot Scandal,” and it has been the bane of Diamond’s existence for years. What good is wealth if no one is willing to accept your money? She’s been doing everything in her power to prove that she’s different, that she’s not her father, that she’s not the type of pony she was when she was younger.
And these efforts are often in vain.
“Well, you can’t blame a mare for trying,” she mumbles as she begins to walk down the dirt road towards Sugarcube Corner.
This has been her life for some time. Even in the face of her family’s humiliation, their business is still going strong. She’s made some bold moves to expand their influence, and with what successes she has attained, she’s been trying to give back to the community. Countless projects across Equestria were founded, at least in part, by her, not to mention all of the charities she’s supported.
Others would sooner be broke than accept her money, such as the stallion from moments ago. He runs a charity for disaster relief in some of the more “accident prone” areas of Equestria, like the badlands and near the Undiscovered West. She can only hope they’re doing well enough on their own to help without her support. While many see her acts of generosity as blatant attempts at trying to improve her family’s image, Diamond herself just sees it as doing her duty. She has the wealth and status to make meaningful change, and she’d be remiss to not at least try… even if her parents disagree.
She lets out a deep sigh. Right now, none of that is important. She’s supposed to meet up with some friends for lunch, and she’s been looking forward to it for some time. It’s been a while since they’ve gotten together like this.
Stepping into the bakery, the sweet scent that could only come from Pinkie Pie’s work immediately assaults her senses. It’s not a bad scent, but definitely a powerful one. A quick glance around the store allows her to locate her friends rather quickly, especially as one of said friends waves her down with a smile.
“There you are, DT! It’s been awhile!”
“Hey hey! Sorry about that, I ran into some unexpected trouble today.”
Diamond smiles at her closest friend, Silver Spoon. When they were foals, she had a tendency to follow Diamond Tiara around like a lost puppy, even after Diamond started changing her ways. Eventually, however, she started encouraging Silver Spoon to carve out a life of her own, and years later, she became a respected surgeon.
Also sitting at the table are three other mares, oftentimes referred to as the Cutie Mark Crusaders. Ever since they were young, they’ve specialized in helping ponies figure out their cutie-mark-related problems. Recently, they’ve taken up advisory roles at the School of Friendship, offering advice for all kinds of creatures in an attempt to help them discover and nurture their special talents.
These four mares make up Diamond’s friend group, and she wouldn’t trade them for the world.
“Let me guess,” Sweetie Belle says with a smirk on her face as Diamond takes a seat, “somepony wouldn’t take your money again?”
“Ugh, don’t get me started,” Diamond groans as she rolls her eyes. “That’s the third time this month.”
“Uhh, Diamond?” Apple Bloom tilts her head. “We’re not even a week into July.”
“I know!” The group lightly laughs at their friend’s annoyance. While her struggles are valid, she finds that having her friends together to make light of the situation makes her feel a bit better about it. “What about you girls? Any juicy stories from the school?”
“Nothing ‘juicy’ enough for the paper, at least,” Scootaloo mumbles before taking a sip of her drink. “Had a changeling that couldn’t change come into our office. The problem seemed pretty obvious to us, but he was less willing to accept it.”
“Let me guess this time. He needed to accept that even though he couldn’t change, he was still talented and needed to value the other aspects of his life?”
“Eeyup,” Apple Bloom matter-of-factly replies. “He turned out to be a pretty good knitter, too.”
“And what about you, Spoon?”
“Me? Oh, you know… just keeping busy.” Silver Spoon looks away while lightly fiddling with her braided mane. “Same-old same-old.”
“Hm?” Diamond leans closer to her friend, her eyes narrowing as her skepticism grows. In response, Silver Spoon leans farther away, eventually running out of space to lean and hitting the wall next to her. With her cornered, Diamond has free reign to get a better look at her. “Are you… blushing?”
“I-it’s hot in here!”
“Ooooooooooo,” Sweetie Belle purrs. “Sweetie thinks somepony’s found herself a girlfriend~.”
“Sh-shut up!”
“Give us the deets, girl!” Diamond backs away, but not before giving Silver Spoon a hearty pat on the back. “Is it that nurse that transferred a couple months ago?”
“N-no! Workplace relationships are a terrible idea, anyway. Especially at hospitals.”
“Who is it then?”
“L-look, we’re not even official yet, so just back off!”
She gently pushes Diamond even further away, and the group chuckles at her embarrassment once again.
“Hehe, come on girls, she obviously doesn’t want to talk about it.” Apple Bloom leans back in her seat before taking a nonchalant bite of her pastry. “Besides, you don’t have room to pry here, Diamond.”
“Hm?” Diamond locks eyes with Apple Bloom, who gives her a cocky, half-lidded grin. “Wh-what are you talking about?”
“Come on, DT. I saw it.”
“Saw… what?” Scootaloo sounds puzzled as she glances at Apple Bloom.
“Our friend here hasn’t been tellin’ us everythin’.” She leans across the table toward Diamond, causing her smile to quickly fade. “I saw you and your little boyfriend last week while finishin’ up my buckin’.”
“Th-that’s preposterous,” Diamond sheepishly replies as she turns away, much like Silver Spoon was doing moments ago. “You didn’t see a darn thing, Apple Bloom.”
“Oh? Because it looked to me like you were kissin’ on him and everythin’. Had to get on your hind legs and–”
“Stop!” Diamond’s face is beet red as she closes her eyes and slams her head on the table in embarrassment. “They don’t need to hear the details. Not from you.”
“Maybe we shouldn’t be picking on her, either.” Scootaloo rubs the back of her head as she looks down at the face-planted Diamond. “If she wants privacy, let’s let her have it.”
“No,” she groans. “I should probably talk about it.” Slowly, she lifts her head from the table, her light-pink coat doing an excellent job at hiding the red mark she acquired from doing so. “Apple Bloom is right. I got a boyfriend.”
Sweetie Belle and Silver Spoon gasp despite the information not being particularly surprising.
“Who? Tell us! Tell us everything!”
Diamond Tiara hesitates as she glances between three pairs of excited eyes and a pair of cocky ones. After a moment, she sighs.
“You know Anon?”
“...I-I’m sorry.” Sweetie Belle looks as though she shut down for a moment before speaking up again. “Did you say ‘Anon?’”
“Yes?”
“Like… the human, Anon? The alien that ended up here after a freak magical accident? The dude that’s twice our height? That Anon?”
“Y-yeah?”
“Uh…” Sweetie Belle glances at her other friends as she tries to think of what to say. “Good… for you?”
Diamond Tiara narrows her eyes.
“You hesitated.” Sweetie Belle winces ever-so-slightly. “Why did you hesitate?”
“I’m just… surprised, I guess.”
“Why?”
“He doesn’t seem like your type, to be honest.” Scootaloo shrugs. “I didn’t even know you were acquainted.”
“Um, DT?” Diamond looks at Silver Spoon, who wears a concerned expression. “You’re aware of the rumors going around about him, right?”
“What rumors?”
“That he’s… you know… creepy?”
Diamond’s brow furrows, her face contorting into a mixture of anger and confusion.
“I’m sorry?”
“W-well, most ponies don’t know anything about him. He’s super distant and quiet all the time. He’s always staring at everypony from a distance. Nopony even knows what he does for a living! Or where he lives, for that matter.”
“So, what? Everypony is judging him because they don’t have the guts to go talk to him?”
“I-I’m just repeating what I’ve heard!” Silver Spoon raises her hooves innocently. “Honest!”
Diamond stares at her friend skeptically for a long moment before finally sighing and glancing across the table.
“You’ve all heard these rumors too?”
“Eeyup.”
“Uh-huh.”
“Rumors tend to fly at the School of Friendship. Ironically.”
“And have any of you actually spoken to him?”
“I have,” Apple Bloom says while looking just as cocky as when the conversation started. “He’s a pretty cool guy. Helped around the farm for a bit when he first got here and needed a job. Doesn’t even need to buck the apples, he can just reach ‘em.”
“At least you understand,” Diamond says with a relieved sigh.
“Mind filling us in on him, then?” Scootaloo takes a bite of her muffin, clearly much more invested in the conversation now than she was before. “I don’t know a thing about him.”
“Well,” Diamond begins, her voice noticeably more airy and pleasant than before as she stares out at nothing. “He comes from a humble family. Had some nice parents that he misses dearly, but they didn’t have a lot of money growing up. He always dreamed of going to school to learn welding, but they couldn’t afford it.”
“Just how expensive is schooling where he’s from?”
“Shhhh!” All three Crusaders shush Silver Spoon, preventing her question from being answered.
“So, he worked as a garbage man a couple of towns over from where he grew up. It wasn’t the most glamorous job, but it was important and he got by. Then he woke up here one day.” Diamond begins to smile a distant, wistful smile. “Princess Twilight told him there was nothing they could do. After being allowed to stay in the castle for a while, he decided to start job hunting.”
“That was around when he found the farm,” Apple Bloom adds.
“Right. He worked a few odds and ends where he could until Mayor Mare approached him, figuring she could help him find a job. After that, he volunteered to be Ponyville’s garbage collector.”
“Wait, what?” Sweetie Belle tilts her head. “Why haven’t we seen him around, then?”
Diamond Tiara sighs.
“He always does his job at night. He says he knows that ponies think he’s creepy, so by doing it at night, he doesn’t have to be seen as often and can therefore freak fewer ponies out.”
“Isn’t that counterintuitive? Wouldn’t ponies think he’s less creepy if he put himself out there more?”
“He’s still perfectly active during the day, he’s just… surprisingly easy to miss. Between you and me, I think he doesn’t have the best self-image.” Diamond reaches over and steals a sip from Silver Spoon’s tea before continuing. “Anyway, he got a small house near the Everfree. Not far from Fluttershy’s place, actually. And… that’s his story.”
“But where do you come in?”
“Oh, we met at Octavia’s charity auction. He was talking to the proprietor after the auction ended, just like I meant to do. I had donations unrelated to the items being sold and all that. Turns out, he’s a bit of a philanthropist in his own right.”
“Does being a garbage collector even pay that well?”
“Better than you’d think, but he’s still one of the less wealthy creatures in town. He tries to make an effort to donate to local charities, though.”
“You sure it’s not just a tax write-off?” Sweetie Belle asks critically.
Diamond’s smile disappears as she locks eyes with Sweetie, a growing frustration evident on her face. “You mean like what ponies say about me every day?”
“O-oh.” Sweetie awkwardly glances at the table. “...Sorry about that.”
“Anyway,” she sighs, “we got to talking. He had no idea who I was, which was a breath of fresh air. It’s nice meeting someone that doesn’t know about your family’s past. I guess that was a part of why I liked talking to him so much.”
“Is he a good conversationalist?”
“Hah! Not even remotely! Dude’s as awkward as can be, but not for lack of trying. In spite of that, we figured out we have a lot in common. We both have a thing for philanthropy, we’re both really good at managing money, and we both… well…” Diamond starts to blush. “We both make each other smile.”
“Awwwwww!” Silver Spoon lightly pokes Diamond in the cheek. “I’ve never seen you get like this! Especially over a guy!”
“So,” Apple Bloom interjects with intentional snark, “how did that lead to the two of you makin’ out over at–”
“We bumped into each other again a few nights later,” Diamond hastily interrupts, “and he was shocked to see that I was the mare living in the Rich family manor.”
“I’m guessing his opinion of you didn’t change because of it?”
“He seemed impressed that ‘rich folk like me’ would be so interested in charity. Said he wasn’t used to it.”
“I mean… he has a point.” Scootaloo rolls her eyes. “They don’t tend to be. No offense.”
“None taken. My dad certainly hasn’t helped that image, that’s for sure.” Diamond taps her hooves together. “Anyway, we decided to meet up for lunch the next day. One thing led to another, and here we are.”
“Suckin’ face just outside my farm?”
“Will you stop bringing that up?!”
Apple Bloom lets out a hearty laugh.
“Sorry Diamond, but it’s not often I get ammo for teasin’ ya.”
“He really means a lot to you, doesn’t he?” Sweetie Belle grins at Diamond while shuffling in her seat. “You keep smiling when you talk about him.”
“...Yeah.” Appropriately, her smile returns as she stares at the table below her. “Ponies always treat me like I’m different, you know? Whether it’s because I’m rich, because I’m a Rich, because of my cutie mark, because of how I was when I was a kid… they always have assumptions.” She chuckles. “Anon? He sees right through me. He knows all of that stuff, and he teases me about it! Says he doesn’t care one bit about that.”
“I take it he doesn’t care about your whole ‘getting others to do what you want’ thing, either?”
“He says cutie marks are… well… I believe he used a word I’d rather not repeat.”
“Excuse me?” all three crusaders ask in unison.
“N-not in a bad way! He just feels very strongly about the fact that they don’t factor into a pony’s character. ‘It’s how you treat others that makes you special, not some talent you have stamped onto your butt.’” While quoting Anon, she makes sure to lower her voice in an attempt to replicate his manner of speech.
“Yeah, a lot of non-pony students say something similar,” Apple Bloom mumbles. “I guess that just leaves one more question.”
“And that is?”
“You really find an alien like him attractive?”
“Very,” Diamond says without a hint of hesitation.
“...F-fair enough.”
Suddenly, the door to Sugarcube Corner opens. Pinkie Pie’s familiar, cheerful greeting rings out, causing the girls to look towards the entrance. Diamond Tiara ducks beneath the table as she sees the new arrival while her friends all start to smirk.
Walking up to the counter is none other than Anon. He towers over basically everything in the room, but he wears a gentle smile on his face. His clothes are modest, and a bit of sweat has formed on his brow from the early afternoon sun.
“What can I getcha, Nonny?”
“Well,” he quietly answers with a hand on his chin, “what would you recommend getting somepony who might be feeling down?”
“That depends.” Pinkie leans over the counter a bit, her face suddenly much less cheery. She takes matters of baking very seriously. “What kind of down are we talking?”
“I think DT might be in for a bad time today. She intends to visit a certain charity, but I met the proprietor of the place she’s going to just yesterday. He really doesn’t like her family, and I don’t know if that meeting is going to go super well for her. I was hoping I might be able to give her something to make her feel better.”
All of Diamond’s friends glance at her conspicuously, and she makes a shushing motion with her hoof.
“Hm… what kind of give?”
“Excuse me?”
“The manner in which you give a treat is extremely important to the reception of that treat. Are you going on a date with her? Gonna knock on her door?”
“I was hoping to… uh… ‘accidentally’ bump into her?”
“You need a double cudgeon blueberry muffin. And since this is Diamond Tiara we’re talking about, I’ll make it a low-carb one. Just the way she likes them.”
“Thanks, Pinkie. I don’t know what I’d do without–” Before Anon can finish, Pinkie Pie whips out a paper bag that seemingly has the aforementioned muffin inside. “...You. That was fast.”
“It’s a serious matter, so I did some serious baking.”
“How much do I–”
“It’s on the house. Now get out there!”
“I can’t possibly–”
“I said MOVE!” Pinkie, in a surprising show of strength, pushes Anon all the way out of the bakery. “And good luck!” She waves as the door closes, leaving Anon alone to shrug and begin walking away. After a few moments, she looks directly in Diamond Tiara’s direction. “Alright, you can come out now.”
“Ugh.” Diamond slowly rises, her face beet red from embarrassment. “Thanks, Pinkie.”
“Did you hear all of that?” Silver Spoon grins ear to ear as she excitedly leans on her friend. “He’s thinking about you!”
“Y-yeah.” Diamond fiddles with a napkin while not daring to look any of her friends in the eyes. “I heard.”
“That was cute. Sucks that you had the surprise spoiled,” Scootaloo remarks as she rests her hooves behind her head. “And I guess we know for a fact that he’s not faking his affection or anything.”
“What are you waiting for, girl?!” Sweetie Belle stares at Diamond with wide eyes, catching her off guard.
“What do you–”
“How’s he gonna ‘bump into you’ if you’re in here?! Go get your man!”
“I, uh, okay?”
“Go!” Silver Spoon practically shoves Diamond out of the booth. “Your beloved awaits!”
“Don’t call him–”
“Good luck!” Scootaloo jokingly exclaims with a wave.
“And give him a couple dozen more smooches for me,” Apple Bloom says while stifling a laugh.
“Ugh, you’re all the worst.” Diamond Tiara smiles and rolls her eyes as she heads for the entrance. “Same time next month?”
“Wouldn’t miss it!” they all respond.
With a nod and a noticeable spring in her step, Diamond Tiara rushes out of Sugarcube Corner, eager to meet up with her boyfriend.
“I’m glad she found someone,” Scootaloo quietly remarks. “She’s pretty enough that you’d think it’d be easy, but it’s still kinda surprising.”
“I’ve never seen her so giddy.” Silver Spoon laughs to herself as she watches Diamond rush off through a nearby window. “I think he’ll be good for her.”
“You mean like your new girlfriend is for you?” Apple Bloom leans back in her seat and smiles a cocky smile once more.
“Apple Bloom, don’t tell me–”
“You girls all gotta find a better place to make out than my farm.”
“Shut up!”
As the group laughs off the unexpected situation, Diamond Tiara excitedly makes her way down the street towards Anon. It’s true that he’s not the most “conventional” boyfriend, and it’s also true that their relationship will likely only cause the rumors surrounding either of them to grow. He comes from a very different walk of life than her, and their thoughts, experiences, and life trajectories couldn’t be any farther apart.
But that’s exactly why she loves him.
Author's Note
I've been promising this one for quite a while, huh? You're welcome, Caladis. 
I plan to return to this storyline in the future. I had more ideas than I could fit in a one-shot, haha! 
As always, I appreciate any and all feedback!
