Pokemon Yellow: Now, I was young, and my knowledge of RPG's was limited, by my history with Blue and Red version taught me that, if you leveled your main Pokemon and nothing else, you'd do fine. Then I arrive at Pewter City, and also arrive at the rather damning conclusion that a Pikachu can't fight rock/ground Pokemon. I died 12 times, and didn't pick it back up for 3 months.
Final Fantasy X: My first TRUE RPG experience, once again my lack of knowledge kicks me squarely in the balls. After listening to Seymoure yammer on and on, I finally get a chance to stick my sword in his exposed chest, only to learn the hard way that consistently running from battles due to impatiences tends to leave you up shit creek without a paddle when it comes to bosses. Deleted my file, didn't play for months.
MAG: I like MAG, I really do, but if no one else is listening, it's not worth playing. Oh, and grenade spam which seems to be completely effective when you're on defense, but useless when you're on attack.
Every Fighting Game Ever: I suck, end of story.
Prof. Layton and the Pointless MacGuffin: Anyone of those goddamned slider 'get the ball in the hole' puzzles.
World of Warcraft: Wrath of the Cataclysmic Lich Crusade: Any 'Multiperson' quest I solo'd as a Warlock now attempted as a Paladin.
Final Fantasy XII: Going through one battle, learning about the license grid, either or.
Rock Band: When your one friend starts failing on purpose so your start strangling him with the mic cord.