Celebrity Dating Game

by Dandereshy


Rarity

The next morning, you get up early to do laundry. And early meaning noon instead of afternoon.

Your wardrobe is limited to begin with, so wearing your last pair of clean clothes meant it was time to use the ol' washer and dryer in your basement.

As you descend into the dark, damp cellar, you miss a step and go tumbling down the stairs, cursing and yelling the whole way down. Unfortunately, this wasn't the first time you fell head-over-heels for your basement. This house was designed for ponies, not bipedal primates. The ceilings frequently grazed your head, as well. It was a good thing you were short by human standards, otherwise this might be far worse for you than it already was.

Groaning and recovering your few pairs of clothes from the dusty floor, you fill up your basket and bring it to the washing machine, loading it all up and turning it on.

"And now it's time to eat," you grumble, trudging back upstairs. On your mind was the strange but successful date last night with Egghead. She came on pretty strong when she brought you to her home, the library, which totally caught you by surprise. You didn't take her as the kind to want it on the first date.

What did she mean by what she said, anyway? you ask yourself as you pour milk into your oatmeal, something you always did in your world. 'It's tradition for a male to court the female on the first date.' What? First time you've ever heard that one. Must be why Equestria is so heavily populated.

Sitting at your small, round, wooden table that Applejack made for you, you devour your breakfast, still deep in thought.

Maybe you had to change up your game a little, switch up your methods. Or, perhaps it was too early. After all, you'd only dated Twilight so far. You still had five more to go.

You shiver violently. How would those go?

Finishing up your meal, you place the bowl in the sink and have a seat in your living room, on the couch and take up a novel you were reading. About 30 minutes later, the washing machine signals that your load is done and ready to be tossed in the dryer, so you jog---carefully---down the stairs and move your clothes to the other machine, returning to your book moments later.

Inferno had to be Dan Browns' best novel ever. It was more captivating to you than Da Vinci Code, another favorite of yours. The guy was a wizard at writing these thrillers. Although his vocabulary included dozens of words that prompted a dictionary check every five minutes, the stories he wrote were amazing and intriguing.

You were about to read a third chapter when you smelt smoke.

"Aw, shit."

You toss the book aside and race downstairs to find the dryer billowing smoke.

"How does this even happen?!" you bellow, grabbing a jug of water from your food and water stash nearby and swing the dryer door open, dousing all the contents with the whole jug of water. Unfortunately, the damage was done.

You drag your smoldering clothes from the dryer onto the floor and prod it with your foot, searching for any signs of life, but alas, your clothes had bitten the dust.

Sighing heavily, you plod up the stairs. Time to pay Rarity a visit.


Clear on the other side of town, the Carousel Boutique is quiet when you enter, the bell above the door the only noise you hear. You close the door and look around at all the gowns and crap she was working on. "Hello?" you call out, taking a few steps forward. "Anybody---er---anypony home?" Gotta keep up with the latest spoofs.

A few seconds pass before a white unicorn with a swirling purple mane comes rushing down the stairs, her horn aglow as she uses magic to hold the dress she was adding trim to high above her head. "Yes? Hello? Who's there?" She stops at the bottom of the steps and smiles at you. "Oh, hello Anon. What brings you here?" She sets the dress aside to deal with you.

"My dryer hates my clothes," you tell her the short version of the story.

She seems confused. "Um... What do you mean dear?"

You sigh. "Clothes. Gone. Dead. Need new ones. All I have now is what I'm wearing," you motion to your outfit, which thankfully was your favorite, the one you came to Equestria wearing.

She nods her understanding. "I get that, I suppose. But what happened? Where's the rest of your wardrobe? Did you lose it?"

"My dryer cooked it."

She was visibly appalled. "I always hated that thing. Ever since Twilight helped you make that wretched contraption, I've despised it. And see, my dislike is totally justified." She tsks a few times and makes her way to the supplies layering the nearby workstation. "Well, I can remake your original clothing, but I advise not using that... thing... from now on." She gives you a pouty look over her shoulder. "Do that for me, will you dear?"

It was at this point that you decided on who to date next.

You take a few steps closer to her. "Sure, sure. Whatever you want. Just, uh, one thing. I'll stop using it for something in return."

"Aren't I doing something already by making your wardrobe a second time?"

You wave your hand, as if tossing her words away. "That's expected of you. There's something else I'd like from you." You grin and waggle your eyebrows.

She raises one of hers. "Yes...?"

You take a deep breath. "Go on a date with me. Tonight."

At first, she didn't seem too willing, but then she gave a pearly-white smile. "Why, Anon, that's a perfectly reasonable trade."

Sweet! That was easier than you thought. "That's what I wanted to hear. So, what time should I come by to get you?" you ask, ready to mentally note a time and place, if need be.

She trots past you, the smell of glorious perfumes wafting up into your nose. "Oh, you're not going anywhere. We're going right now!" She turned and went up the stairs, leaving you wondering why you were going on a date with preppy pony at 2 pm.


After a two hour wait, Rarity came down wearing some exquisite gown, looking like she was about to marry. She took you and went to see Twilight, who didn't have much to say to you, but blushed constantly and avoided eye contact. Rarity asked her friend to teleport the two of you to Canterlot, which she did.

Now, you weren't exactly dressed to date this mare, but upon voicing your concerns, she blows them off, saying 'beauty is in the eye of the beholder.' Of course, it'd be the pony that sleeps with makeup on to tell you that.

You've been to the famed Canterlot a few times, and it never ceased to remind you of how badly you wanted to reenact Assassin's Creed. The very medieval-styled town was just begging to have you climb its many stone structures and leap from high walls.

However, you wouldn't be able to do any of that, at least, not right now. You had a Rarity to date.

Roaming up and down the streets, you try to start up a conversation with your "date".

"So," you start, walking beside the second real date you've ever had. "Why'd you pick Canterlot for our date?" Clearly a dumb question, based on the look you receive.

"Canterlot is the premier dating place. It's studded with high-class eateries, eloquent clothing retailers, and magnificent jewelers!" Her voice grew louder as she answered.

You scratch your head. "What did the last two have to do with dating?"

She rolls her eyes, as if it was obvious. "They had everything to do with it. It means dating can be about as glorious as it can get here. One can be dressed stunningly whilst wearing the most beautiful jewelry and eating at the most elegant of restaurants. See? They fit like a puzzle." She returns her attention to the businesses around the two of you, her mane bouncing with each step.

Now, normally the preppy girls were not your type, but Rarity was simply beautiful, without a doubt. This was probably the only time you'd ever want to listen to the way these kinds of girls talk.

Nodding in response to what she just said, you take a look around you, noticing that you were the only one not dressed for a gala. "So, what do you like most about Canterlot? Between those three things you told me?"

"Hmm," she goes into thought, staring straight ahead and frowning. Finally, you ask a good question. "I would have to say... Perhaps it's... Hmm..."

You seemed to have stymied her. This was going to be an interesting night. "Rarity," you interrupt her thoughts, placing a hand on her shoulder and earning a curious gaze. "Maybe you can tell me over some dinner?"

She stops and points at the sun, still far above the horizon. It wouldn't set for couple hours. "It's customary to have the dinner date after the sun sets. I'd rather go sightseeing, instead. Wouldn't you dear?"

You give that some thought. What else was there to do? It's better than walking around aimlessly while listening to her mumble on about fashion and crap you didn't care about. "That sounds good. Lead the way," you reply, flashing a quick smile and winking.

She returns the smile and takes your arm in hers, making you have to lean and wobble as you walk. She tugs you to the next few places to visit.


Long after the trip around town, you sit in a fancy three-hoof restaurant with Rarity sitting across from you at your table for two. She chose this restaurant, saying and promising that the food would "leave me speechless." It was. Thirty bits for a bowl of salad and bread? And that was only her meal.

The dim lighting and quiet, classical music being played live made the atmosphere far more romantic than the date with Twilight. Not only that, but Rarity was visually prettier than bookhorse.

As you chow down on a sandwich whose name you couldn't possibly pronounce, Rarity decides to ask a question.

"What made you ask me on a date, Anon? This has been a question on my mind all evening." She nibbles a piece of seasoned bread and sips from a teacup.

You stop, halfway between chewing and swallowing your bite of food. You decide to swallow it and answer. "Well, it's obvious that you are beautiful and classy, right?"

"Mmhmm, yes, but that doesn't answer my question. Why did you ask me on a date?"

This was not a question you expected to have to answer. For any of the mares you were dating. You sit back in your chair and smile innocently. "Uh, well, maybe I just felt a connection?"

She didn't look too sure. You couldn't keep telling what she expected to hear. She wanted the truth, and she was going to get it, most likely. "Anon, you know better. Please, tell me so my mind can be at ease." She takes another sip of her drink.

A waitress comes by and fills up her cup, so you wait until she leaves to reply. "Okay, so honestly I like you. Normally I don't do preppy girls, but you're different. You're smart, reasonable, beautiful, talented, and friendly. I guess I like those traits."

This time, she doesn't question you, or even appear dissatisfied. She actually gives a little smirk. "Well, well, well, Anon. How long have you been harboring these feelings from me?" She bats her eyes.

Gulp. "Uhhhh a few hours," you say, nabbing your sandwich and taking a big bite, chewing slowly. This was so you had an excuse not to talk, so you could think about your reply when she asked you a question.

She draws back a little. "A few hours? That seems a bit... Off." She pushes her plate forward, obviously done eating. "What brought this on?"

You had to get off this subject! She was picking you apart with this. Sooner or later she'll be digging into your personal life and that was a no-no. There were too many weird things in there, like the crap you used to look at online at school.

You take your time chewing, then swallow, opting for a drink before you answer her. "The fact that you selflessly offer your skills to make me clothing without making me pay is one thing. Another is how well you carry yourself. It's... Attractive," you say mysteriously.

This seems to satisfy her finally. "Oh my, that's quite the compliment. What better way to get to a mare's heart than to compliment her kindness and beauty. Anon, I had no idea you were such a charmer." She rests her elbows on the table and her head on her hooves, staring into your eyes and batting hers.

You begin to sweat. "Heh, yeah, I am a charmer, aren't I?" You look back her and laugh nervously.

She continues to intimidate you with her beauty. "So, is there anything else you'd like to do tonight, my dear? It's getting late. We should head out now, if you don't mind."

You quickly stuff your face with the rest of your burger and place the appropriate amount of bits on the table for the waitress to recover whenever she comes back. You stand up and pull out the chair for your lovely date, and help her out of the chair, taking her hoof.

You know, that's a good question... When the hell did you become so chivelrous and charming? Watching porn certainly didn't teach you.

She is flattered by your moves and allows you to lead her away, back to the streets. The moon is now full and halfway into the sky.

On the clearing streets, you walk with the famous Rarity and you were actually pretty happy. This was not part of the plan. You weren't supposed to enjoy these dates. They were just for company!

Instead, you're walking down a cobblestone road in Canterlot with Rarity, and you're happy. Happy!

You must've been possessed for this. This wasn't you. But you didn't want it to stop. This was fun!

Rarity must've noticed your internal conflict, as she tugs on your arm and stares up at you, concerned. "Is there something bothering you dear?"

You rub your head. "Oh, no. Sorry. I was just thinking about some stuff. Let's get you home." You lead her back to where Twilight dropped the two of you off. This was where you had to be for when she came back to pick you up.

Rarity went quiet, but you knew she wasn't satisfied with your answer.

Twilight came a few minutes later and brought you both back to Ponyville, where you again led your date to her home and business, without much words in exchange. At least, not until you got to her place.

Standing with her at her door, you both are pretty awkward. You decide to speak up, breaking the silence. "So, uh, that was fun. Did you enjoy it?"

She places a hoof on your hand and smiles lightly up at you. "Very much. Perhaps we can do it again very soon?" It was more a hopeful question than anything else. Honestly, you wondered the same thing. Unfortunately, you had to date the other four mares before you made a final decision.

"Maybe. But the night doesn't have to end now..." You let that hang.

She raises and eyebrow and frowns. "What do you mean?"

You shove your hands in your pockets. "You know... Love, of the physical kind." Boy, this was harder to ask than to reply to. Twilight's a boss.

Rarity is not amused. "Anon, that is much too quick. We hardly have feelings for each other. Why would we do such a thing on the first date? Why, you'd be lucky to glimpse my hindquarters on the tenth date."

Now you're confused. "I thought it was tradition to engage in... That... On the first date?"

Rarity shakes her head adamantly. "Oh no. Whoever told you that? Proposterous. Anon, I'll see you tomorrow. I'll finish making you your clothes and bring them over. It's been a great night." She leans over and kisses your cheek, smiles, then retreats into her house, leaving you standing alone, out in the dark street.

"Alrighty then."