Ships and Boats, But Mostly Ships - Collab

As a foal Pipsqueak never stayed in one town long enough to develop a real attachment to it, though he did have fond memories of a few. When he grew up, he continued traveling, the only life he had ever known, seeing everything in Equestria.

The first place he settled down for more than a few months was Manehattan. There was always more to see in that city, a life that suited him perfectly. While there, he visited a few nightlife hotspots, but his favorite was a bar near the Orange Hotel. There, he found a perfect drinking buddy.

Her name was Babs Seed. She was an heiress of one of the wealthiest families in Manehattan, not that she ever talked about that. She just wanted good friends and good cider. And him. Celestia, she wanted him. At first he was just that out-of-towner with the most interesting stories she’d ever heard, but talking to him night after night, she began to realize he was smart, funny and hot.

So a few months later, when he said the urge to travel had caught up with him again, and he’d be moving on in a week, it hurt. It hurt enough for her to make a stupid proposition. Since he was going to be gone in a week, she said, they might as well mess around a little, right? Well, that got his attention. Every night that week, after they left the bar, they’d head back to his apartment and have some fun.

She never told him she was in love with him.

He didn’t find out until a few years later, on Nightmare Night, when both of them decided to visit a little town from their youth. When they bumped into each other, and, through the confusion that comes with an impossible coincidence, she managed to say,

"There’s somepony I want you to meet…"