When I got married, I had some clothes and gifts that a few ex-boyfriends gave me. None of the things were really my style and often had bad memories associated with them, so I ended up selling them all on eBay and socking the money in my retirement fund. These were all perfectly nice things, so I didn’t see any reason why they shouldn’t go to someone who would like to have them (while funding my retirement at the same time.)
I also had a sister-in-law whose former boyfriend broke it off with her, but who had given her quite a lot of jewelry. She ended up auctioning it off and making several car payments with the extra money.
But if these are perfectly good CDs, teddy bears, items of clothing, etc., I don’t see why you should feel one bit of guilt about either selling them or donating them to charity, or re-gifting them, if you don’t like the idea of money changing hands. They won’t do anyone a bit of good in a landfill!
I had a boyfriend who liked to give me stuffed animals when I’m not the sentimental type, so I donated them all to Toys For Tots. I like the idea of those unwanted toys becoming some child’s beloved companion.
And when you sell an article to someone on eBay, that item gets a whole new “life” with new associations for the buyer. What might have been a memento from an old boyfriend to me suddenly becomes that great bargain someone else picked up!
Perhaps I’m just unsentimental, but that approach has worked just fine for me. I just don’t like the idea of having a lot of either clutter or bad memories around.
~Jaden(name removed by moderator)