Twilight Sparkle was on her way to the Ponyville schoolhouse with a million butterflies in her stomach. This time, she wasn’t going to pick up or return books. She had no errands to run, no duties to fulfill, nothing that could help her put it off. Today, she was going to ask Cheerilee out.
 
The pep talk from her friends and the second talk from her son didn’t ease her nerves at all. She had no idea what she was doing. How did one even ask a mare out, let alone date? She only had experience with stallions, and those relationships didn’t even last. And wouldn’t Cheerilee be weirded out by the proposal, so soon after Twilight’s husband died? Did Cheerilee even like mares?
 
The alicorn finally got to the schoolhouse, her heart racing as she tried to compose herself just outside the door. Relax, Twilight. It’s just like any other time you’ve seen her! You’ve talked to her then, you can talk to her now! But I’m asking her out—no, it’s just like talking to a friend but a little closer! Use the flirting tips Rarity and Rainbow gave you!
 
Twilight turned the doorknob, pushing the door open. Don’t knock, Rainbow had said. Just go in. Show her you mean business.
 
“Twilight? Hi!” Cheerilee looked up from her papers in surprise, putting on a smile. “What brings you here?”
 
Be smooth.
 
“Heyyy,” Twilight drawled, her face growing hot as she struggled to keep her voice level. “You…come here often?”
 
Cheerilee blinked. “I work here.”
 
Oh shoot! Twilight’s heart jumped into her throat. Just try something else! Offer her something, like Rarity said! Or show off for her!
 
“Well, I’m sure you could use some help with that work,” Twilight sauntered slowly into the room, trying to keep her legs from shaking as she swished her tail a little too far for effect. “I’ll do anything you want…”
 
“Twilight-“
 
“And oh, is this an apple?” Twilight picked up the fruit from the teacher’s desk. “I bet it’s really…juicy.”
 
“I’m going to stop you right there,” Cheerilee snatched the apple back just as the alicorn took a bite. “Twilight, what’s going on?”
 
Twilight spit out bits of apple as her face flushed hot red. “N-nothing!”
 
“Are you…flirting with me?”
 
“N-no?”
 
Cheerilee smirked. “It’s okay if you are. It’s cute-“
 
Twilight’s heart jumped. OhCelestiashethinksI’mcute-
 
“-but are you actually courting me, or is this some kind of elaborate joke?”
 
Twilight gulped hard. Her friends didn’t say anything like this would happen. Nobody did! But then—her mind went back to what Dusk told her. Be yourself, Mother. If she likes you back, she likes you for you. Just let it come naturally.
 
She sighed. “No, I…I’m actually courting you. For real.”
 
Cheerilee’s eyes widened in surprise. “Really? So soon after Flash’s death? I know you two were having a hard time but—“
 
“I know, I know! We don’t have to! I’ll get over it!” Twilight waved her off. “It doesn’t matter that much! It’s just a schoolfilly crush!”
 
“I don’t know, it must have mattered enough for you to come into my classroom unannounced and eat my apple,” Cheerilee chuckled. “And hey, you can’t help how you feel, I suppose.”
 
Twilight could only squeak and bury her face behind her wings. “Will you go out on a date with me…?”
 
Cheerilee gently grabbed her wings and moved them aside so she could see her face. “I don’t see why not.”
 
“R…really?”
 
“Sure, it’s not like I have anything else going on…or anyone else.” It was now Cheerilee’s turn to blush. “How does Saturday at the Ponyville Cafe sound?”
 
A huge, dorky grin spread across Twilight’s face. “That sounds GREAT!”