My guy *usually* insists on paying for everything. I've never asked him to take me out to overly expensive places though out of respect because I know he'll want to pay. I almost always offer to pitch in towards whatever we do and he usually says no. Also, if we're going to dinner, he encourages me to get whatever I want, but I usually try to make it equal or cheaper than his meal unless I'm really craving something else.
As far as driving goes (I'm still in school 3 hours away from where he lives) usually he drives here to visit. If he does I try to chip in on gas if I can afford it.
There have always been times in our relationship where I take HIM out to dinner/on a date & let him order the most expensive thing on the menu if he wants.
Men like to be spoiled every now and then too.
In this economy though, he's had some problems finding a good job since graduation, so we've been splitting things more often. If we go to the movies, he gets the tickets, I get the snacks, or this past weekend, he bought our pizza for our movie night & I bought us ice cream afterwards. He still usually feels guilty about me paying for things.