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Been riding most of my life. Here is my advice to a prospective beginner:
1: Take a msf safety course. They teach good habits, and you'll get a much much much better foundation this way. Having a buddy who has a bike teach you in a parking lot is a bad idea. You'll inherit his mistakes and bad habits, and he won't be as thorough as the msf course.
2: Buy yourself a cheap japanese bike. Preferably a standard or a really non-agressive baby sport bike. Cruisers aren't the easiest to learn on, as the riding position isn't ideal for newcomers. Same goes for aggressive sport bikes. Preferably 500cc or so. 250s are great to learn on, but you may run into wanting to upgrade soon. A 500 is still easy to learn on, and you can totally grow into it a bit. Suggestion: Suzuki gs500 or Ninja 500. Both are absolutely great beginners bikes, (suzuki is a bit better of a riding position, but ninja 500 is fine). They can also be had for super cheap prices since they've both been out forever, and you can get a good example for under 1800 bucks.
3: Don't buy your dream bike that you think looks bad ass. You're probably going to drop this first one a few times. You don't want to learn on something you're too busy babying. Plus, if you buy a 15yr old japanese bike to learn on, you can sell it back for just about the same price as you paid for it, so there's no financial reason to not buy a 'beater' first bike.
4: Don't ride with a group for a while. It can be a bit chaotic. Just spend some time learning basics. When you no longer have to think about what you're doing, then try riding with one or maybe two friends. You don't want to be a beginner in a pack of a dozen bikes, it's a bit unnerving at first.
5: Have fun, and be careful. Wear a helmet. Wear gloves. Wear boots. No shorts. Even a small "off" at 28mph is enough to lose skin and crack your head open. Proper gear goes a long long way.
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