I'm living with a roommate, who I love, but the problem is her STUFF. It's everywhere, and there's a ton of it! I don't want to use the word hoarder, but we're getting there. How do I approach her gently, before we both get buried?
Writing from Under a Pile of Clothes
The relationship with a roommate is a delicate one. Similar to how good fences make good neighbors, I'd say that good door-closing habits make good roommates.
If you want to approach her because you're worried about her well-being, you're better off waiting until she's not your roommate anymore, lest you appear to be presenting your own judgmental housekeeping needs under the guise of friendly concern. If, however, you want to approach her because you can't stand to live like this or because there are real health and well-being concerns for both of you, then talk to her about standards for common areas. As much as her piles of dirty laundry and old Starbucks cups might disgust you, if they're in her bedroom, you don't have a lot of recourse. But, if they're in the kitchen and, say, you have bugs or rodents as a result, then it's well within your rights as a roommate to demand a change (kindly, of course).
One helpful option is to pass the blame. If you are having a problem with pests (and I can't imagine how you aren't, since even the cleanest apartments in Philly seem to be afflicted), tell her you want to get the landlord involved, but you know he won't be willing to take responsibility unless the apartment is clean when he comes over. That way, you can unite against the common unfairness of being tenants and any future infractions can fall under the category of "we really don't want to deal with the pests/pesky landlord."
Another option is to tell her that you plan to do some cleaning. Tell her you really like the common areas being a certain way, but you don't want to mess with her, ahem, mess, so would it be all right for you to move everything that's hers into her room? Then do it. Move every last cup, coin and copy of US Weekly. Make neat piles, but make it clear that these things don't belong where you can see them.
If, just supposing, we're talking about your roommate having too many books, or too much furniture or too many pots and pans, rather than keeping actual trash around, ask her if some of it could be moved out of the apartment. Offer to help clear things out, or look into storage options or arrange a list of sale items for Craigslist.
I know you say you love your roommate, but maybe you'd make better friends than living companions. That way, you can keep loving her without the touch of resentment that is bound to creep up if she doesn't shape up. As soon as your lease ends, plan to move in with someone whose living style you've already vetted to be sure it's more in line with your own. Or, better yet, find an affordable one-bedroom or studio so that when it's messy, you have no one to blame but yourself!