I have to say, I am VERY obsessed about milk. I will NEVER drink milk past its expiration date. In fact, I will only drink milk up to 4-5 days after the day I bought it, and then I will toss it! My milk MUST be fresh. If it smells not as fresh as the day I bought it, I toss it.
And for all other foods in the fridge and freezer, if it's been in there for a week, I toss it. Exceptions are water, sliced cheese, salad dressings, ice cream, and all frozen foods, etc. I like all my food to taste VERY fresh. If I have cooked foods and put leftovers in the fridge, I throw them away after 1 week. Yeah, I'm very fussy about my food!
Medications - well...because the date has expired does not necessarily mean it's automatically bad. Here's an article about that:
Drug Expiration Dates - Do They Mean Anything?