I used to have issues giving things away to the thrift store... I would feel so bad about "abandoning" the objects that I had chosen to get rid of. I thought that they must feel so rejected and heartbroken being stuffed in a bag and tossed out just like that. I always imagined them missing all their friends in my room and wondering what they ever did to deserve being thrown away.... I remember imagining other people getting their hands on my things and abusing them or breaking them, and I couldn't bear the thought of letting them go to a bad home.
I mostly did this with stuffed animals or other toys or knick knacks with faces, but I also remembering sometimes feeling this way about clothes and shoes. I would decide to thin down and start sorting through things and putting things in a big trashbag, but then after a while, I would start to feel sorry for one thing or another and fish it back out of the bag to put it back with it's "friends". Before I knew it, my bag was empty and I was even more attached to my junk that before :p
I honestly have never been fond of clutter, so I have managed to overcome this in order to maintain an orderly living space. I have gotten a good handle on it and don't really struggle with it anymore, but I do still have tendencies and have to be careful. Once I imagine myself interacting with an object or refer to an object as if it has feelings, most times I can't help but associate it with having feelings from that point on. (Again, this mostly applies to stuffed animals.)
For instance, one time I had this stuffed animal turtle that I gave to my dog. I had won it from a claw machine I think but I had too many stuffed animals on my bed and needed to thin down a bit. My dad walked in the room and saw my dog playing with it, and he said to me
"Hey isn't that yours?".
I replied, "Oh it's ok. I gave it to him."
Then my dad says (jokingly) "Aww poor guy! He was all happy on your bed and now Teddy's chewing on his head."
I immediately felt AWFUL and proceeded to pry the toy out of my dogs mouth and apologize to it or something. I had to stop and say to myself, "Wait banana, this is ridiculous. This is just a stuffed toy. It's not real. Your dog is the one with feelings" I still took me a little while to come to terms with this and feel okay with giving it back to my dog (who was quite upset about having the turtle taken from him).