“This will never work!” Blueblood hissed from behind the corner. “I’m not submitting myself to such potential embarrassment!”

“Blue, buddy, you got this,” Flash Sentry whispered with a conspiratorial smile. “Just do as we practiced and you’ll be fine!” He tapped Blueblood on the shoulder then shoved him unceremoniously into the street.

The white unicorn stumbled a few steps forward, barely regaining his footing. In front of him, a group of three young mares were giggling in front of the jewelry store, window shopping. Blueblood's face twisted with fear. He turned around, seeking a way to flee. Instead, he saw Flash waving a hoof towards him, half forcing, half encouraging, his lips shaping a clearly identifiable "Get on with it!"

"Humph!" Blueblood pouted. Easy for you to say! You just go out there in your flashy uniform, flap your wings, and mares start swooning! He looked at the mares. Despite himself, he had to admit they did look rather attractive, even if they were nowhere as refined as those in Canterlot. All this just feels wrong! Mares should be wooing me, not the other way around! I'm a prince, after all! There are bound to be herds of—

"Excuse me." One of the mares—a fetching pink coated blonde—turned at him. "Could you help us for a moment?"

Blueblood froze. His ears perked up and his pupils became as small as pinpricks as he returned the mare's glance. She's smiling at me! His tail whooshed in panic. Why is she smiling at me?

"We're having a small argument," she looked over her shoulder at her friends. "And could use a stallion to resolve it for us."

Be calm, Blueblood. You can do this! Take a step forward and accept their challenge. Put your vast knowledge of literature to good use! Make good of the words of Browning and Wordsworth: compliment their eyes, their mane, their hooves, then calmly and gallantly accept their request with three-eights of a smile.

"Umm, uh-huh." Blueblood nodded. Drat!

"Great!" The mare almost immediately pulled him in front of the store window, where several items of jewelry were displayed. "So, tell us. Which of these would most suit an earth mare?"

Okay, I was off to a rough start, but I can do it! I know more about fashion and jewelry than half of Canterlot! It'll be a breeze to point out that the sapphire horn-ring is clearly the most exquisite of the trinkets on display by far, its radiance nearly as beautiful as their eyes...

"Umm, I dunno," he muttered. Somewhere behind, Blueblood heard the unmistakable sound of a facehoof. "Umm, the brooch." He pointed at the first thing that caught his attention.

"Really?" The mare tilted her head. She was no longer smiling.

"Uh-huh?" Sweat trickled down Blueblood's face. This is a disaster! I feel so embarrassed! I knew it was a bad idea to go to this backwater village! Last time I let Flash talk me into—

"Ha! There!" The mare stomped her hoof on the ground, her eyes narrowed in a smug expression. "Told you it's the brooch!" One of her friends pouted, while the other rolled her eyes. "Thanks," she added gently, then pecked Blueblood on the cheek. The Prince tried to react, to thank her, to make a compliment, anything, yet his body didn't budge. His eyes stared forwards, refusing to blink... until a wing gave him a sharp slap on the side.

"Blue, what's wrong with you?!" Flash frowned. "Those were prime dating material! The blonde one even did all the talking, and you still choked!"

Well, if you hadn't shoved me out there like a common peasant, maybe things would have gone better! Blueblood raised his chin indignantly. In truth, though, he had his doubts. As much as he hated to admit, his dating—and social—skills were non-existent. He was the highlight of social events and balls, but a few minutes in private would make even the most forgiving mare leave. Flash, by contrast, had been with so many mares that he had been forced to transfer to the Crystal Empire to get a pony of female persuasion even talk to him.

"Look, it's really simple," Flash began. "All you have to—"

"Will you stop bringing up 'the good old days'?!" Blueblood snapped. "We’re not in school anymore. I'm not Shining Armour, and I'm definitely not you!" He added a slight snort at the end of the sentence. "I can't just go and start a random conversation. I need to think a bit. Plan things."

"Blue, all you need to do is be spontaneous." Flash placed his wing on Blueblood's shoulder. "Just look at a mare and compliment the first thing that grabs your attention. You bump into somepony? Great! Tell her how you have to stop meeting this way. You're waiting in line for something? Offer to exchanges places with the cute mare behind you, as long you get to chat with her. If she has a nice mane—"

"Yes, yes." Blueblood removed Flash's wing from his shoulder. "Eloquently put, yet utterly pointless. Let's just go home. I've had enough for one day."

"Buddy, you've tried to talk to one mare!" Flash frowned. "Seriously, trust me! You can't go wrong! All you need to do is say a few words. The moment a mare hears your Canterlot accent, she'll become putty in your hooves. These small towns are all alike. Tell them you're from there and they think you're related to Princess Celestia."

"I am related to Princess Celestia," Blueblood grumbled.

"So what are you worried about?" Flash nudged Blueblood in the flank. The Prince gritted his teeth. "Now focus, take a deep breath, and give a compliment to the first mare that comes out of this jewelry shop."

"This is laughable," Blueblood moved a step away. Nonetheless, he did glance at the shop door. Oh, to Tartarus with it. He's already dragged me this far. What do I have to lose? "Just one try," he said adamantly.

"Absolutely." Flash nodded in faux support.

"And I just give her a compliment of some sort?"

"Yep, yep."

"And if she ignores me, we go back to the Palace?"

"Bro, I'll fly you there myself!"

Well, that sounds reasonable. Blueblood looked at Flash, then back at the shop. Door. Mare. Compliment. It sounded so simple in his head. The "perfect infallible plan" as the pegasus would put it. A bit too perfect, maybe, just as Celestia's grand galas.

The jewelry shop door creaked open.

Let's just get this over with. Blueblood closed his eyes, then trotted forward in the most dashing trope he could muster... smack into somepony. The strong smell of lilac perfume told him it was a mare.

"Oh, dear me," he carefully articulated every word, making it sound as Canterlotean as audibly possible. "We have to stop meeting like—" he froze. "Rarity?!"

"Oh." The unicorn he had walked into narrowed her eyes and not in a good way. "Good morning, Prince Blueblood."

Author's Note

Chapter 1 Blue, you got this!
Chapter 2 ???
Chapter 3 ???
Chapter 4 ???
Chapter 5 ???
Chapter 6 ???
Chapter 7 ???