"Keep it, toss it, burn it, sell it "
In the same vein as last Chat's game, except this time I am giving you the items:
1. old high school/alma mater t shirt
2. love letter from old flame who broke your heart
3. engagement ring -- from when you said "no"
4. vinyl edition of what was "your song" - you can download from iTunes anyway.
This is easy. I had an old Brock University T-Shirt I kept until is basically disintegrated. I went and bought a replacement a couple of years ago. I am a guy, of course I love my well worn comfy clothes. This does however, get a little challenging as I have three Alma Mater's (not including two high schools). Man, do I ever get a lot of phone calls asking me for money. Although my heart is still with my undergraduate education.
I would toss the love letter - I probably would not have kept it anyways though it would have been cool to include in my memoirs one day. You know when I magically get rich and famous and people might actually give two squats about my life.
In theory, the promotion of Disco Demolition Night at by the Chicago White Sox was good on paper but the execution not so much.
This is an easy one - the ring of course. I am cheaper than I am sentimental.