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I recommend that he stay away. I speak Russian and Ukranian and it was hard enough for me.
If he does go, it is IMPERATIVE that he dress like a local and wear nothing expensive or fancy. Cheap coats, cheap jeans, cheap everything. A cheap indiglo-type watch is a very handy thing to have, as is a small flashlight, a lighter (whether he smokes or not), plenty of Kleenex packets (you can never count on toilet paper being readily available unless you're in a western hotel), and every vaccination known to mankind. Particularly important is that he have a current rabies vaccination, because if you get bit by a dog over there you're completely fucked otherwise.
By the way, an excellent way for him to get his ass kicked is to wheel out his German in a bar. Those old Soviets have long memories, and everyone there lost someone in the war.
He would also be advised to search Google for scams people play on tourists and read every single page he finds. Most involve money, fake cops (plus the corrupt ones you mention), dishonest cabbies, exorbitant bar tabs (you order a bottle of wine, not knowing the price has been set at a thousand dollars, and your order is legally binding), good samaritans who offer to "help," and so on.
No offense, but your nephew is an idiot and is very likely to be sorry. Going over there alone, as a westerner with no knowledge of Ukranian or Russian? I can't imagine too many things less bright than that.
If you care about this kid at all, put a stop to it. You can start with the following facts (I don't meant to scare you, but I think I have to):
1.) AIDS is roughly 10 times more common over there than it is here. The number of pretty females who are ready to jump a westerner for a chance at a green card is staggering, but finding a clean one is not always easy.
2.) Male-on-male rape is far more common over there than it is here, and sex trafficking isn't limited to young girls.
3.) Lots of young males who disappear wind up as slave labor in some distant eastern mountain range. Governments know about it and do nothing because of drug kickbacks.
4.) Because he'll be traveling alone and it will be obvious to everyone around him, his chances of getting drugged by someone with bad intent are roughly 50-50. The best case scenario if that happens is waking up with no wallet, passport or cash. The worst cases are described above in items 2 and 3, as well as outright murder.
Seriously, your nephew would be safer getting sent to a maximum security prison on child molestation charges. A teen traveling in Ukraine (or anywhere in Eastern Europe, for that matter)? It's practically suicide.
BTW, his Canada hat won't fool anyone. Every American claims to be Canadian over there, and nobody buys it. By the time your nephew passes through customs and has his passport stamped, every cabbie waiting outside for him will already have been TOLD he's American (cell phones with pic messages). He's going to be the sucker with the big red target on his back, and will be the only one in the postcode not in on the joke.
There are no words for how idiotic your nephew's plans are. Good luck - you'll both need it.
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