(image courtesy of the artist chantal powell's flickr page. be sure to check out her website and her blog)
g.c. asks "I'm curious to know your opinion on the matter of keeping old love letters and letters from people who are no longer a part of your life. My bag includes letters from a former friend (who betrayed me), as well as former beaus. Aside from two of the beaus with whom I've stayed distant friends, I have no contact with the others. Part of me wants to keep them all, as they are a log of my past loves. However, I wonder what purpose that serves? I could justify keeping everything because 'it's just one piece of paper or one letter', but times that by 100 -- and you've got quite a stack of paper!"
My philosophy is to only take and keep things in your home that you love, use, and that add to your life in some way. There are so many things we can't control, things that make us feel bad, but we can control what we surround ourselves with in our home.
I suggest keeping only the things that bring back positive memories, or elicit some kind of a positive response. After time, memories become detached from certain physical things and contact with them doesn't bring up any memories - those things should be easy to let go of. As for the those that bring up bad memories I personally don't see any reason to keep them. Forgive, let go and move on.
I will add (as with anything else in your home), you may not be ready to let go of it and maybe that's ok. Keep it until you are, unless you believe that by holding onto it you are holding onto the pain which is affecting you in some way. Then this is a good time to go through the process of letting go. Some people burn old letters and things as a way to cleanse themselves or whatever... I just recycle them!
I'm a professional organizer who lives and works with a 'living better with less' philosophy. I'm not a minimalist but believe you should only take things into your life that you love. That your home should not only support your functional needs but be beautiful as well.