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At home. I used to play in school, until I realised that my work and exams were far more important that Pokémon, no matter how much fun it provided. :/
I usually play obsessively at home or anywhere where I won't be seen. Occasionally I'll play with friends who understand HOW FREAKING AWESOME THE GAMES ARE, but most of them are very sceptical of any Pokémon past #151. So I guess out of my current SoulSilver team they would say I only have 3 real ones... damn purists!
EDIT: Oooh would you look at that. Over two years on this site and I've finally reached 100 posts. Take that society!
Home
Car trips
Friends house
families houses
plane
train
Random places
And if your so scared to play Pokemon in public, then you really need to think. Are you really that scared about what other people think of you? If someone asks if I like Pokemon, I say yes. One of my teachers said "Does any one remember Pokemon?" when we were talking about things we used to like, and I said in front of everyone, "I still like it."
Since I have the Nintendo DSi XL/LL, it's a bit bulky to take it with anywhere I go and playing Pokémon on the subway (main transportation I use) isn't the most convenient time. So most of the time, I'd be playing Pokémon at home.
I play at home, Over at my friends house, in the car, I can't play at school because if I did My DS would be gone. I even have to keep my Pokewalker hidden while I'm at school.
I generally play it... wherever I am... whenever I'm bored. Well... if I have my DS with me, anyway.
Typically I just play it at home or at a friend's house though. XD