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I’m going to tread on sacred ground here, discussing issues of such profound importance they are never discussed out loud.
The Rules about eating your roommate’s food:
1. Don’t eat the first one
Maybe the main reason for this is that you have to open the package, thereby leaving evidence of your filching.
2. Don’t eat the last one
If they were saving that last cookie, bagel, beer, etc., they’ll know it’s gone. It’s heart rending to enter the kitchen for a tasty treat only to be forced to endure another bowl of ramen.
Pretty much everything between the first and the last is fair game.

Exceptions:
Cheap beer
There’s nothing sacred about your roommate’s cheap beer, particularly if it’s sitting next to good beer. You’re doing everyone a favor by getting that crap out of the way. Taking the last e.g. Coors Light is praiseworthy because, that crap got skunky, like, a month ago. Dude, way to take one for the team.

Hot pockets
There’s only two in a package. The Rules would imply that you could never steal a roommate’s hot pockets. This is not so. There are several extenuating circumstances to consider:
1. Are there multiple boxes of hot pockets? If so then one hot pocket will not be missed.
2. Are you in hot pocket equilibrium with your roommate? This delicate balance shifts back and forth but, due to lack of record keeping, is largely a matter of perspective.
3. Is your roommate out of town for at least two days? You don’t want those things going bad on you.

Anything else
If you plan on replacing it before your roommate could possibly want it. This can be a particularly effective strategy. For instance, if your roommate has bought deluxe cookies, you can polish them off and then replace them with some crap like Chips Ahoy.

The Milk Zeno’s paradox
The Rules do apply to milk but since milk is, on kitchen length scales, continuous, there is a bit of a problem defining “the last” in relation to milk. With milk and other continuous substances the rule is that you can take half of what’s left. A back-of-envelope calculation shows that if there’s ~100 g of milk left, then, following the rule, you’ve got about 80 uses of milk until you get to the last molecule. Of course, your cereal is going be pretty crunchy with just a single molecule of milk on it. But maybe you should quit whining and go buy some damn milk.