3:05 PM, on a Friday. All the ponies at the Canterlot University were celebrating the end of school, and the start of a three-day weekend. Parties were being planned, dates were being scheduled, and everyone was having a good time.
Only one unicorn was not joining in the festivities. Her name was Twilight Sparkle, the personal protégé of Princess Celestia. It was a well-known fact that Twilight Sparkle was the school valedictorian for five years running, and she even had more raw magical power than some of the teachers.
She also had the social skills of a broken gazebo.
Twilight Sparkle currently had her nose stuck in a book, as she walked down the hallway. She didn't take any notice of the other ponies, who were all talking about their plans for the holiday. There was one pony in particular, though, who was taking notice of her: a reddish/pink unicorn with a short, dark mane and small blue glasses.
This is it, he thought. Time for me to finally talk to her. No big deal, right? She's only the most famous pony in school.
"The square of the sum of the hypotenuse of the radius times the denominator—" Twilight muttered to himself.
"Hiiiii Twilight," the colt said.
The unexpected noise completely threw Twilight for a loop. She looked up, and smashed into her book. This caused her to trip, which made her smash into a nearby wall.
The colt flinched. That looked painful.
"Oh my gosh, are you okay?" he asked, as he went over to Twilight and held out her hoof towards her. "I didn't mean to startle you!"
"You made me lose my place!" Twilight Sparkle complained, as she grabbed his hoof and pulled herself back up. "Why did—you—huh?"
Twilight suddenly noticed that the pony helping her up had a well-defined snout and angular cheekbones. It took a second for her to process this information. She was close—somewhat close—to a pony with a square-shaped face.
Jeepers, it's a colt! Twilight thought. She instinctively jumped backwards in fear, which caused her to smash into the wall again.
The colt frowned slightly. This conversation was getting off to a bad start. He was beginning to regret his decision to approach his secret crush.
"Twilight, are you okay?" the girl asked.
"I...I'm fine...uh...John," Twilight Sparkle said, resisting the urge to scream and run away. Her boy senses were tingling, because he was a boy. A boy! An actual boy! Talking to her!
"My name is Longsight Spellen," he said, a little disappointed that Twilight didn't know his name. "We've been in the same homeroom for three years."
"Uh...uh...yeah..." Twilight Sparkle said.
She had no idea what to say. Various thoughts popped into her head, but they all sounded wrong. I like your glasses? No, that sounded creepy. Homeroom class sure is...homeroomy? No, dumb, dumb. Will you please be my boyfriend? No no NO!
Twilight swallowed heavily, as the silence grew longer and longer. Great, now she looked stupid, because she couldn't think of anything to say, and this colt was going to hate her forever because of it, and she was going to ruin his one chance at true love, and why is it so hard to talk to other ponies?
"So..." Longsight said. He was slightly nervous, and the conversation (or lack thereof) was kind of creeping him out, but he was determined to continue. Twilight Sparkle completely misinterpreted the message he was sending, though.
Oh, no, he's angry at me now! Twilight thought. Think! Think! Uh...the weather! Dad says no matter what, you can always talk about the weather!
"It's a sunny day today!" Twilight practically shouted. As a matter of fact, it was somewhat cloudy that day, but Twilight hadn't actually looked outside.
"That's right!" Longsight said, looking somewhat relieved. "It's the perfect day to watch some hoofball!"
Hoofball. The only thing Twilight Sparkle knew about hoofball was the fact that it was some kind of sport. As you might expect, Twilight Sparkle was not very big on team sports, or really, any sort of activity which involved working with a lot of other ponies.
"I have two tickets to the hoofball game tonight," he said. "And I need someone to take with me."
This was the cue for Twilight Sparkle to say, "I'd love for you to take me to the hoofball game!" Needless to say, she missed the cue completely. Instead, she blinked in confusion. "What about your parents?" she asked.
"Huh?" Longsight Spellen asked.
"Can't your parents take you to the game?" she asked. "If it's too far away for you, I'm sure they can give you a ride."
Longsight Spellen frowned. Did she somehow not think he was a grown adult, capable of taking care of himself? What kind of college student still needs to have their parents take them everywhere?
Twilight Sparkle smiled. After some original trouble, she had the sense that this conversation was going smoothly! Score two points for Twilight!
"I mean, I need somepony to go with," Longsight Spellen clarified.
"Why do you need somepony to go see your parents with you?" Twilight Sparkle asked.
"I don't!" Longsight Spellen said.
"But you just said you did," Twilight said.
"I didn't!" Longsight Spellen said. "I mean—I have two tickets to the hoofball game, and I'd like to take—"
"Your parents!" Twilight Sparkle said. "You're going to give the tickets to them! That's really nice of you!"
Longsight Spellen facehoofed.
"Say, I'm going to a family dinner tonight," Twilight said. Her brother, Shining Armor, was back in town after a long absence. "Do you think I should get something for my parents, too? Maybe they'd like hoofball tickets!"
"Ugh, forget it!" Longsight Spellen said. He stomped away, muttering something about a thick-headed pretty-girl.
Twilight Sparkle watched him go, a frown spreading across her face.
He seemed nice for a colt, Twilight Sparkle thought. Too bad he didn't ask me to go to the hoofball game with him. I totally would have said yes.
About an hour later, Princess Celestia was wrapping up her meeting with Prinny, the principal of Celestia's School for Gifted Unicorns. These monthly meetings helped keep Celestia informed of the day-to-day goings-on at the school.
"And lastly, we have Twilight Sparkle," Principal Prinny said.
Princess Celestia sighed. Here it comes... she thought. The faculty always seemed to have some sort of complaint against Celestia's personal student. It was probably because Celestia accepted Twilight as a student without getting their approval first.
"She's a very good student, but we're concerned about her social skills," Principal Prinny said. "She doesn't seem to interact well with the other students. In fact, whenever she's in a class that grades for participation, she does rather poorly."
"I am aware of this," Celestia said. "As I have explained before, I see no reason why a magic school should grade for participation. How much a pony talks in class has nothing to do with her ability to cast spells."
"That's not all," Principal Prinny said. "After charting Twilight Sparkle's grades over the past several years, we can see a distinct pattern."
"And what is that?" Celestia asked, curious.
"Male teachers," Principal Prinny said. "She does poorly in classes with male teachers. I've talked with a few of them, and they tell me that Twilight Sparkle refuses to speak in their classes."
"So she's a little shy around stallions," Princess Celestia said. "That's perfectly normal—"
"Normal for six-year-olds," Principal Prinny said. "Not grown adults. And I get the sense that she's not merely shy around stallions; she is deadly afraid of stallions."
"Aren't you exaggerating just a little bit?" Celestia asked. "I'm sure that she's not that afraid of colts."
"She accidentally set a classroom on fire, when one of her male classmates unexpectedly touched her shoulder," Principal Prinny said. "She screamed once, when one of her male teachers called on her, out of the blue. And when we were doing square dancing in gym, she ran away and hid so she wouldn't have to get close to any colts."
Princess Celestia smiled. If she had to do square dancing in gym class, she would run away too.
"I will make sure to deal with this problem," Princess Celestia assured Principal Prinny. "After all, I am personally responsible for Twilight Sparkle."
She thanked Principal Prinny for his time. As the Principal left the audience room, Princess Celestia's next visitors came inside. These visitors were members from the Summer Sun Celebration committee.
"Your highness, we have finished investigating the possible sites for this year's Summer Sun Celebration," said the leader of the committee. "Manehatten would be the best choice, although Hoofington claims to have a larger budget, and—"
Celestia paid little attention, as he droned on. The Summer Sun Celebration had been held in Manehatten for the past forty years, due to the fact that everyone on the committee lived in Manehatten. And since Celestia knew what the committee would say, she let her mind wander.
The first thing she thought of was her student, Twilight Sparkle. Principal Prinny had been completely correct in his assessment of Twilight Sparkle's poor social skills. Twilight had promised to try harder to meet new ponies in the future, but apparently, she had been unsuccessful.
But what could the princess do? She was Twilight's teacher and mentor, not her life coach. There was no way that Celestia could force Twilight Sparkle to meet other ponies. Could she?
The beginnings of a plan formed in Princess Celestia's mind...
"And in conclusion, we have unanimously decided that Manehatten should host the Summer Sun Celebration," the committee leader said. The other committee members nodded, satisfied. "Can we expect your approval?"
"No," Princess Celestia said.
"Ex-excuse me?" the committee leader asked.
"I've already made my decision," Princess Celestia said, in a kind, yet authoritative voice. "The Summer Sun Celebration will be in Ponyville this year. I'm putting my personal student, Twilight Sparkle, in charge of the project."
Poor Twilight Sparkle had enough problems on her own, without the help of scheming princesses, however. At the family dinner that night, it was obvious that Shining Armor was still the favorite child.
I'm not jealous, Twilight Sparkle thought to herself. I'm not jealous. My brother has a perfect life, and I'm not jealous.
"So now that my tour of duty in the Griffon Kingdom is over, I'm back here at Canterlot," Shining Armor said, bringing an end to the long story of his many adventures over the past few months.
"Why, that's wonderful, honey," his mother said happily.
"It sure is!" the father said. "A promotion, and you get to move back home!"
"Better yet, I hear that Captain Whitewings is planning on retiring in a year or two," Shining Armor said. "As second-in-command, I'll automatically take his place when that happens."
The proud parents clapped in joy, while Twilight Sparkle felt like throwing herself out the window. What was next? Shining Armor had a supermodel girlfriend?
"Well, now that you're back in town, we simply must have more of these family dinners," the mother said. "I want to hear all about your new life."
She didn't ask about my life, Twilight Sparkle thought. In fact, nopony has asked me a single thing all night. Some family.
"Sure," Shining Armor said. "That'd be perfect."
"How about next week?" the father asked.
"No good," Shining Armor said. "Next Friday, I have a date with my marefriend."
"Oh?" the mother asked. "And what does she do?"
"Her name is Fleur de Lis," Shining Armor said. "She's a model."
*BAM!*
Twilight Sparkle slammed her head against the table, hard. This caught everypony's attention, and for the first time that night, both parents looked at her.
"Are you okay?" the father asked.
"Yeah, I just...slipped," Twilight said.
Shining Armor blinked. "Sorry for hogging the conversation," he said. "What's been going on with you?"
"Oh...the usual..." Twilight Sparkle said. She gave a little half-laugh. "Still studying..."
"Do you have a job yet?"
"No..." Twilight said.
"A coltfriend?"
Twilight Sparkle felt her face grow hot. "I don't...I haven't...I don't have time for dates," she muttered.
"Why not?" the mother asked. "I'm sure you'd make a fine marefriend for somepony."
"Maybe you haven't been looking hard enough," the father said.
"Hey, we can't all be dating French supermodels, okay?!" Twilight Sparkle snapped. "Can we change the subject, please?"
The family was stunned into silence by Twilight Sparkle's outburst. She smiled awkwardly, then shrank down on her haunches. Where was a good teleportation spell when you needed one?
Twilight let out a huge sigh of frustration as she went into her room. There is no way that tonight could have been any more awkward, she thought.
To Twilight's surprise, Shining Armor came into the open doorway. Twilight thought Shining would have gone directly to his own room, after that disastrous dinner.
"Hey, Twilight," Shining Armor said. "I could tell something was bugging you at dinner, but I didn't want to mention it in front of Mom and Dad. What's wrong?"
"Nothing's wrong," Twilight Sparkle lied.
"I can tell that's not true," Shining Armor said. "You can't fool me. I'm your BBBFF, remember?"
Twilight Sparkle sighed, then walked over to her brother and nuzzled him lovingly. "This is going to sound stupid," she said. "You know I love you and everything, but...I'm really jealous of you."
"Jealous of me?" Shining Armor asked. "Why would you be jealous?"
"You have a perfect life," Twilight Sparkle said. "Everypony loves you, you get to do all these interesting things, and meanwhile, all I've been doing is studying."
"But you love studying," Shining Armor said.
"I do," Twilight Sparkle said. "But sometimes, I wish I could be you. Your life is great, and mine stinks."
Shining Armor rubbed his sister's hair. "Aw, come on, Twiley," he said. "Your life isn't so bad. I mean, you're Celestia's personal student! That's a pretty big deal."
"Mom and Dad don't seem to care," Twilight Sparkle said. "All they're interested in is the fact that you have another perfect marefriend, when I'm still single. Five years from now, I'll still be single, and you'll probably be married to a princess or something like that."
Shining Armor laughed. "Unlikely," he said. "But it's not a competition or anything. I'm not trying to show you up by getting better dates than you. You know that, right?"
Twilight said nothing.
Shining Armor didn't trust the look in her eyes. "Right?" he repeated. "I know Mom wants grandchildren, but—"
"That's not it," Twilight said. She felt her eyes start to tear up. "I...I've never been on a date."
Shining Armor looked shocked. "What?" he asked.
This was the wrong thing for Shining to say; Twilight began to cry in earnest now.
"All the other girls talk about colts all the time, and no colt will even so much as look at me!" Twilight cried. "I'm going to be all alone for the rest of my life!"
"Oh, Twiley," Shining said. He gave his sister a big hug, and he held her until she exhausted her tears. "I'm sure the perfect colt is out there, waiting for you."
"No he's not!" Twilight wailed. "They're all mean, or scared of me because of the Princess, or they don't like me because I can't talk to colts! It's impossible!"
"It's not impossible," Shining Armor said. "Remember your Prom? You were really nervous about getting a date then, but you found a nice colt to go with you."
Twilight sniffled loudly. "Spike is nice, but he's not a colt," she said.
"You took Spike to Prom?" Shining asked.
"Oh, that's right," Twilight Sparkle said. "I guess you weren't here when that happened."
"When what happened?" Shining asked. "I thought you asked that Thunder guy, or whatever his name was."
"I did," Twilight said. "I asked six stallions to go with me. All of them said no, I wasn't pretty enough, or no, I'm too much of an egghead, or no, he can't go because he's lactose intolerant, like that has anything to do with anything!"
Twilight slammed her hooves on the ground with anger. She took a deep breath and continued.
"Thunder was the one who said yes," Twilight said flatly. "Then, two hours before Prom, he sent me a letter saying he found somepony better than me to go with."
"What?" Shining Armor asked. "He turned you down at the last minute? That jerk! I think I'll send the castle guards to teach him a lesson about how to treat mares!"
"Forget it," Twilight said. "That was five years ago. I haven't seen him since."
Shining gritted his teeth, still mad on his sister's behalf. "Why didn't you tell me about this when it happened?" he asked. "I could have done...well, something to help you."
"I was embarrassed, okay?" Twilight asked, hanging her head low. "That was the closest thing I've ever had to a date, and it was a complete disaster."
"But like you said, that was years ago," Shining Armor said. "Haven't you asked anypony out since then?"
"No," Twilight said quietly. Asking stallions to go with her to Prom had been the most terrifying ordeal she had ever gone through, next to the entrance test to get into Princess Celestia's School for Gifted Unicorns. Twilight had no desire to repeat the experience ever, ever again.
"And...nopony has asked you out on a date?" Shining continued.
"No, of course not," Twilight said glumly.
"Well, that doesn't make sense," Shining said. "My little sister is so pretty and smart, I would have thought the stallions would be knocking down doors, trying to see her."
"Maybe knocking down doors, trying to get away from me," Twilight muttered.
For a moment, Twilight wondered if she should mention the colt who talked to her at school that day. He fit all of Twilight's requirements for the perfect coltfriend: he was cute, and nice, and most importantly, he was an actual colt who was willing to talk to her.
Twilight sighed. Who was she kidding? She'd never be able to date Alan...whatever his name was. No colt would ever date her. She was a failure.
"Look, just forget it," Twilight Sparkle said. "I'm a hopeless case. I'm no good with colts, and they're probably all scared of me, because I'm Princess Celestia's personal student. I should forget about dating and worry about studying."
Twilight walked over to her desk, where she picked up a letter from Princess Celestia, which had arrived earlier that day. It had something to do with the Summer Sun Celebration, but Twilight hadn't had a chance to read it yet. Celestia was the only—
"That does it," Shining Armor declared. "We'll make next Friday's dinner a double date."
"WHAT?" Twilight Sparkle asked. The letter from the Princess slipped from Twilight's magic and slid under the table.
"Me and Fleur, you with somepony else," Shining Armor said. "That way, if anything goes wrong, I'll be there to help you."
"You...you'd do that for me?" Twilight Sparkle asked. "You'd find me a date?"
"Sure, no problem," Shining Armor said. "I'm sure Fleur knows somepony who's around the same age as you."
"YES!" Twilight Sparkle cheered. She began jumping around in a circle. "Yes! Yes! Yes! Yes! Yes! Yes! Yes! Yes! Yes! Yes! Yes!"
Twilight Sparkle completely forgot about the letter from Princess Celestia. It would later get thrown out by accident, and Twilight wouldn't learn she was in charge of the Summer Sun Celebration until the day before it happened.