When I rent a game I play on Easy so I don't have to renew it. When I play a new game I play normal so I can get the story relatively quickly and still have fun. I play Expert when I've played before.
Easy/normal for games that you generally play through a couple of times, i.e RPGs, but I work my way up to (and then settle at) the highest possible difficulty for games like Guitar Hero because it's so damn fun.
When I start playing a new game I will most often play it on the hardest difficulty. This is usually followed up by my realizing I'm pushing myself too hard and starting over on the next setting down.
I am, and always will be, in it for the storyline, which is why I mainly play RPGs. Thus, I always go on the easiest difficulty first. If I'm any good at it, I might go higher.
..of course, this may just be an excuse to hide the fact that I'm usually God-awful at anything BUT RPGs, but you're never gonna know that.
I usually pick Hard mode first if it's available, but occasionally, in cases like Call of Duty 4, I go on Veteran my first time through. That was not a very positive experience for me.
I have way too many games I still need to play to play through anything on hard. Playing on easy lets me finish them quicker thus lets me move on to the next one. Why must there be so many brilliant games, and why must I only have the vacs to play them in?!
With most games, I'll play at the recommended difficulty level on the first run through; whether that's through an in-game check (CoD) or on the descriptions (Halo), I'll see what the guys who made the game recommend.
When replaying a game I've already finished (unless I only made it by the skin of my teeth or something) I'll dial up the difficulty a notch or two to keep it challenging.
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