Have you ever won something and then wished you hadn't?

I won a bottle of beer and two glasses in a pub raffle the year I started work. It came in large cardboard packaging and was awkward to carry around. I didn’t particularly want the bottle of beer, and I had no use for the glasses.

Thank you for asking this question, as it made me realise something (which I hadn’t considered before).

In 2016, I want to say, I won a local photography competition, with the subject of “autumn”.
I was very excited, and felt proud.
Before the results were announced I even thought I would have a pretty big chance to win it, so satisfied I was with my composition.
So, I won (the People’s Choice Award) and was over the moon.
I received my photo, framed, as a prize, which I later gifted to my parents (at last something that potentially gave them a feeling of pride ~).
But….
After that winning, the following couple of years, I went out on photography trips, with the pure intention to shoot another/only winner(s).
I could not for the life of me figure out where my pleasure had gone to.
But now I know.
I went out with a totally wrong goal.
Not to capture beauty, but to stroke my ego.

I “won” opportunities to take extra special classes at school, designed to acknowledge my and my friends’ exceptional interests and talents, which were said to be without requirements other than participation, and then transformed into classes with final assignments, right before finals.

Yay, thanks for teaching why not to sign up for extra classes. It’s a trap!

Recently I won a drawing for a gift certificate for $10. A friend of mine was kind of pouty because I had won it the month before also, and felt I shouldn’t have entered for the current month. Petty, silly jealousy at age 68! sheesh! The other 10–12 people said I had as much right to enter as anyone else. So there! :^P

But now when we have them I hope I don’t win.

I was awarded a sum of $20,000 from an organization about 25 years ago. It was completely unexpected.
I donated it anonymously to a charity.