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Zipp is quite the multitalented athlete but rollerskating was one sport she never bothered checking out - until she met Sunny and saw how much fun the friendly earth pony had zipping around on her twelve little wheels.
Here we see Zipp’s first time on rollerblades, being taught by none other than Sunny Starscout herself, who graciously lent Zipp her own skates for the lesson! And with it came a rare moment of Equestria’s coolest princess being legitimately nervous for once. Savor her adorable distress while it lasts because that mare is a very quick learner.
This drawing is set between the events of My Little Pony: A New Generation and My Little Pony: Tell Your Tale, before Zipp became a rollerblading master in her own right (>>2943540).

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I would certainly be terrified going downhill on skates on a road surface like that. While Zipp being a quadruped and having wings would give her a lot more stability, the risk of one of the skates getting into one of the cracks and suddenly stopping is still a big risk.
Background Pony #6913
As a guy who’s on the fence about skateboarding after a hard fall, I have two things to say:
Keep your weight centered and slightly forward. How you lean and pivot your body is how you turn and steer.
The lower you are, the more stability you got. Adjust your legs accordingly as gravity pulls at your feet.