~Three days later~

You are Anon and you are running like your life depended on it! The wind is whistling past you as you here several calls in the distance.

“Better hurry Nony, Rares reeeelly wants to see you in a dress!” You hear from the pink party pony who is whimsically bouncing beside you.

“Huff~ W-When… ~Huff~ She said… Huff~ “Help Prepare” ~Huff~, for my dates… ~Huff~ I didn’t expect that!”

After several minutes of lung burning cardio, you make it back to your house and Twi is already opening the door. You practically dive inside as a ribbon slaps on the barrier Twi setup around your house. As you catch your breath you see P-Pop declare, “Safe!” while wearing an old fashion umpire uniform. The ribbon slowly slides off the barrier wall by the time you catch your breath and Rares reaches the barrier. “Anon, Darling! Don’t you think you are being a little over dramatic?”

“Nope! I said I didn’t want a dress and even compromised for a kilt on St. Patties Day! You are the one being overdramatic that I will not wear your design… So there!” You stick out your tongue for a second to emphasize how done you are with the situation. You may be able to admit to acting immature, but she started it!

“Hehe, Oh Noni, always so funny!”

“Yeah, I get it P-Pop, see you two later. I got to get ready.”

-1.5 hours later-

“Are you sure you have everything you need?”

“I’m fine Twi, I still cannot believe my marefriends set me up on a blind date.”

“To you, this may be new. But to us, this is normal to do.”

“And I appreciate your efforts. I know this is for all of our goods, it just still feels weird to me.”

You give Both Twi and ZZ a kiss on the lips and wave as you head out.

“I’m off to Sugar Cube Corner. See you both when I get back. If your asleep when I’m back, I’ll see you in the morning.”

“Love you!”

“Journey safe, my Love.”

The cold night’s air nips at your exposed scalp as the stars above twinkle in a gorgeous hue. However, the refreshing breeze and sounds of crickets start to get drowned out by the beating of your heart as you near your destination.

“Table for two, ready and awaiting your arrival.”

Standing in front of where Sugar Cube Corner should be, is a cardboard cutout with a fancy Italian style bistro intricately drawn in what seems to be crayon.

Of course, the mare in front of the door is P-Pop in a waiter’s uniform with a curled mustache holding a candle. Just go with it.

“Thanks P-Pop. Am I the first one here?”

“Of course not sil-Er- Misère, we told you a much later time so your date had time to prepare. Can’t have the male coming way before his date.”

You roll your eyes as P-Pop winks at you. Silly opposite relationship logic pony world.

“This way please!”

You follow P-Pop through the cutout for the door and note that the place has been moved around to make in look cozier. There are small lights strung around the ceiling and candles on all the tables. As you start to smell garlic in the air and your eyes adjust to the new light you finally notice her.

Princess Luna is standing next to the table in the center of the restaurant. Her mane is braided all the way down, holding the stars themselves in a pattern draped over her right wither and around her neck to highlight her smiling face. She is wearing a dark violet dress that seems to hug her frame. Her tuft is half concealed and half lifted by the V on the front that seems to spill over is fabric and fur like a collared shrit trying to contain a cloud.

You look her in her eyes, the deep pools reflect the twinkling light and the smile you did not know you had.

“Your seat, Anon.” Luna says as she pulls out your chair with her magic. You would protest, but no need to embarrass your date by pointing out the obvious problem… just yet anyway.

“Thanks Luna,” you sit down, “I got this.”

“Nonsense, a mare must…” you see the magic incircle the chair underneath you glow then pass through you several times.

You shrug and scoot the chair closer to the table then give Luna a mischievous smile.

“We… I forgot about that.”

“It’s fine Luna, I already said I got it. Also, I’m not a pony stallion. I’m more familiar with the opposite role, but when in Equestria, do as the Equestrian’s do. So, try to relax. I won’t bite, unless you’re into that?”

You casually drink your water as you wait for Luna to calm her wing-boner and take her seat.

~Several awkward minutes later~

“I have to say, you look stunning tonight.”

“T-Thank you! You look rather dashing this evening as well… Oh, I-It seems our waitress is here?”

You see P-Pop sauntering over with a huge grin on her face.

“What can I get the lovely couple this evening?”

You look over the menu and note the lack of most hay products you had expected. Must be going out of their way for you. That’s sweet. You notice something that seems particularly delicious.

“I’ll have the ‘Vegetable Fettuccine Alfredo’ with no mushrooms please. Ah, and a side salad with Prench dressing. Thank you.”

“Very good Sir, and for you Madam? “

“W-I will take the large salad with grilled tofu steak. What wine do you have available?”

“Certainly, and here is the wine menu.” P-Pop pulls a smaller menu from her mane and Luna looks through it.

“A bottle of Canterlot Ponet Grigio will do, thank you.”

“Excellent choice!” P-Pop flourishes a bow while swiping the menus. She then excuses herself before bouncing off to the kitchen.

You can only shake your head at her antics as you stifle a laugh.

You look up to see a quizzical look on Luna’s face, so you tilt your head in the direction P-Pop left and shrug.

Realization seems to dawn on Luna’s face as she too stifles a giggle.

“I’ll have to thank her for breaking the tension, I was honestly a lot more nervous until she started, “you gesture around, “all this.”

“Tis true, I am amazed she was able to set this all up in only 2 days.”

“~Whistle in amazement~ She does have a gift for this!”

“That she does…”

A half minute goes in silence, but your worries are still nagging at he back of your mind. It’s likely a bad idea but, better to get the unpleasantries out of the way first.

“…So, Luna, I got to ask… why did you want to date me?”

Luna freezes with her glass of water halfway on its telekinetic journey to her mouth.

“I-I know it’s rude to ask and all. But, well, you’re a gorgeous pony and a princess too boot! You could have any stallion, or mare for that matter, you wanted, and no one would question it.

Twi and I fell in love over very unique circumstances. I worked very hard to prove to myself that I deserved to be loved by her and later Zecora. Even now, though I really want to keep my word about giving them foals, I’m scared I don’t deserve anymore. I’m scared I will not be strong enough to protect my newly forming ‘Herd’… I know that probably seems weird coming from the ‘Great Slayer of Nightmares!’ who can literally kill with a few jabs of his fingertips, but it’s the truth.

…why do I deserve to date someone as amazing as you and the amazing females I already have?”

Luna’s glass was shaking for some time during your little speech, but eventually that shaking settles and she places the glass on the table. A small smile forms on her lips as she looks down at the table before she slowly raises her gaze to look you in the eyes.

“Sometimes I forget that you are not of this world… Anon, that may have been what it was like on ELerth, but here, even in this age, mares are meant to protect their stallion. For a moment, I worried that you though I was not adequate to protect you. That I was to fragile or not honorable due to my past. Hehe, I was even worried that you would see me as a lesser for you are my teacher in dreams. It seems that these were unnecessary worries.

‘Why did I want to date you?’ ‘Why do you deserve to date me?’. Simple, you are the kind of male who can risk ruining a date with me to make sure you are doing the right thing. You are a strong male who does not see me a prize or a trophy. Most of all, because I want you! I will make you mine and I will bow my head to young Twilight if that is what is required.

Is that good enough?”

You guess you were being silly. You forgot, even with all that has been happening, that you did not have to carry all the burden yourself. You had been delaying these dates until you couldn’t anymore, due to fear of the immense responsibility. You were wrong. It’s never been about having to singlehandedly provide for the herd. You will all work together to share the load, to support each other. Love and friendship for all huh? Well, it’s less likely to be fucked up if we all help you suppose.

“Thanks Lulu. I needed that.”

Luna Blushes intensely at the new nickname.

“T-Tis not a problem, We are happy to help!”

As if on cue P-Pop materializes next to your table with two covered trays and a bottle of wine on a small metal cart.

“Pone Appétit!”

Author's Note

Some may say this is still a short chapter, And to be fair, to most it is. Still, this took a lot of time for me to get even this long. It's just not how my brain works.
This is my Thanksgiving gift to my readers. Have a great day!