Do-over of >>635910 which was in serious need of an update.

Is it just me, or are sneakers and dresses crazy-adorable together?

“So, um, this is a date?”

He still wasn’t sure what made him do it, but he did it. After school, he had walked right up to Sweetie and gave her the note. It was a masterpiece he thought, pure brilliance. The note read: “WiLL YoU go oUt witH me? yes [] no []”

She passed the note back after the longest 5 seconds of his life, with the “yes” checked and a little giggle. Pipsqueak was both on top of the world and wishing he could hide in some deep dark hole below it. But, she said yes!

Oh sweet Luna, she said yes. What was he going to do? He didn’t have the faintest idea how dates worked, where they should go, what they should do! He was going to blow it. She’d hate him, and never want to see him again, and the whole school would know, and no filly would ever go out with him again, and he’d be alone forever, and-

Doomed or not, he got ready for what would either be the happiest day of his life, or the last one he’d ever know. Scraping his allowance together, he managed to buy a small box of blondies and a bottle of lemonade for the two of them. The had agreed to meet near the lake, at a little waterfall tucked away in the hills. The was an old bridge there, and it was a favorite spot of his, a place to get away from the world and make a new one.

And there she stood, in a blue sundress with a nervous little smile. Well, he wasn’t the only one afraid, at least. And then she said it:

“H-hi, Pip.”

Welp, too late now.

They sat down on the bridge while Pip prepared their “meal”. It was an awkward, silent few minutes, until Sweetie spoke up. “So, um, this is a date?” “I…guess?” “Do you know what we’re supposed to do?” “Well, uh, we could try holding hands.” Oh sweet Celestia, Luna, Faust, and whatever other deities might be listening, why oh why did he say-

And she held out her hand, shakily.