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Standing regular means you ride with your right foot at the back of the scooter. Standing goofy means you ride with your left foot at the back of the scooter. You'll need to do a bunny hop in order to tailwhip, so practice the bunny hop until you're confident doing it. The higher you're able to bunny hop, the easier time you'll have tail whipping. Remember to push off with your legs and pull up with your arms so both wheels go in the air. Both of your feet will be in the air at this point. Keep both hands on the handle bars and wait for the deck to come back around. You want your back foot to land on the back of the scooter so the deck stops spinning. At almost the same time as your back foot, you want your front foot to land on the deck of the scooter. At this point, the scooter should drop back to the ground. Both of your feet should be planted on the deck.
Do a clockwise tailwhip if you stand regular on your scooter. Do a counterclockwise tailwhip if you stand goofy on your scooter. Practice bunny hopping. Kick yourself off and do a bunny hop. Use your front foot to push off the deck so it spins around 360 degrees. Stop the deck with your back foot as it comes back around. Place your front foot back on the deck.