I regret buying a Black Givenchy Pandora (medium), bought for full price @ Barney's.
I loved it and wore it every day for more than a month. The first day I had the urge to change out of it, I was horrified: "how could I spend that much and want to carry ANYTHING but this bag?"
For nearly a year, it sat - taunting me. I stopped carrying it with intent to sell. I had never sold a bag, so I was stuck: no idea where or how to begin.
During that time, I discovered tPF, and Bonanza, and Tradesy (knew about eBay, and never wanted to go there..). I bought some used bags - learned a bit about selling. Sold a couple of iThings on Glyde.com, and learned that Tradesy uses an identical approach. I felt OK about listing such an expensive bag with their system.
After many months, I wore her again - she was the PERFECT bag for whatever it was I needed that day. I fell back in love with her, and put her back into rotation. I decided to keep her and love her the way she deserved - to free myself from the guild and let myself love her. I removed the sale listing
Many months later, I received email, saying "Your Bag has Sold for $,$$$". To this day, I do not know how the listing I removed became active again. I called them; learned I could cancel the sale), I deliberated (should I just sell it or not???). I sold her, and I don't regret it.
So why do I regret buying the bag I loved--- then felt guilty about -- then let myself love again? Because it raised my threshold. That bag cost >$2k -more than double what I had spent for any single bag prior to buying her. Thanks to Panda, I learned that I do not want to be at that price point again -- or that if I am tempted (and believe me I have been) - that the happiness to be found there is not proportionately greater. Or, if it feels like the joy is greater, so, too will be the guilt!. (even now, I am coveting a Ferragamo Sookie. See thread: Celebrate - What we Did Not Buy)
It was hard to part with her, but I have learned that I can live without her. (I also purchased Anya Hindmarch maxi zip satchel as a replacement - for less than half what Pandora cost. Still too much, but less-too-much).
What I regret is that Pandora raised my price ceiling. I can now rationalize other purchases with this: "It is not $2,000 - it is only half that!" (see: vintage Chanel bucket, large Ferragamo Sofia, and Anya Hindmarch maxi zip satchel - all four-digit purchases, among many other sub-four digit purchases).
So, this.