Need help with some rules about old girlfriends’ stuff

I am considering moving in about two months. I am in the process of collating many of my belongings. They are currently dispersed all over, eg, in the place I am currently living, my parents’ house, my three offices in Manhattan (don’t ask how, I just have three), and some friends’ apartments. I so far (and this is with little effort) have three large boxes of books I plan on selling or giving away. I also threw away three large garbage bags of old papers that I have no idea why I didn’t throw out years ago. I also have two garbage bags of clothing that I will either give away or throw away, if giving them away is too much work.

But here is my problem: I have been finding all this stuff from old girlfriends. I have rings (and other jewelry), letters, clothing, stuffed animals, underwear, ashtrays (even though I quit smoking years ago), music, books, toys, tzochkies, key chains, fake flowers, alcohol, and countless other things. Are there rules for what I should be doing with this stuff?

I never had one of those giving stuff back ceremonies with anyone as we broke up where we throw our stuff at each other. I, by the way, never got anything back either.

I decided that the clothing goes with my old clothing: charity or the garbage. The alcohol I will drink; that is a New Year’s resolution.

Remember that scene at the end of Top Gun where Tom Cruise’s character throws Goose’s dog tags over the edge of the aircraft carrier as closure. I too have some personalized jewelry, but I do not need closure (I am closed, trust me), and I just couldn’t bring myself to throw away jewelry. So I do not know what to do with that. I can’t give it away as it has someone’s name on it. I can’t really return it, as most of these people are married. (Almost everyone I was involved with got married within a year of breaking up with me. I am really good luck that way. It is weird, I know.) It would be cruel to mail people their old stuff. Right?

I am kind of sentimental about letters. I just save those. Is that weird? I have all these old love letters going back to high school. Am I supposed to throw those out?

I chucked most of the underwear and bras. Couldn’t think of any use for them. Returning those to people who have gained eight sizes since would be way too cruel.

Most of the books are integrated in to my book collection. There are a few I am considering divesting myself of because I never cared to read them then, and still don’t.

What about the stuffed teddy bears, the little toys, the glitter lamp, the marble Mexican bookends, sunglasses, Pencils, posters, sundials, and miscellaneous junk? What do I do?

Also, what am I supposed to do about the stuff that was hand-made for me? I have a couple of knitted things (like scarves, hats, kipot. . . ). How long am I required to store those in a draw before disposing of them?

Finally, is it pathetic to save all those pictures? I have a lot of pictures of a lot of people. Do I toss those too?

I am taking any advice!!!