The best and worst thing I ever won was first prize in a raffle at the local fair. It was an item supposedly worth $1,000.
At the time I was still naive, so I called a friend to share the good news. They said; "My birthday is coming up.". Yes, they expected me to give it to them. And so did every single person who found out about it. Because the friend I called told all our mutual friends. And the mutual friends called me up wanting the item.
Not one of them ever congratulated me or said 'yay' or anything. This rankled because they all called me up when nice things happened to them and I would say 'yay or 'congratulations' or 'that's awesome.' And I didn't ask for any of their stuff. But the time something good happened to me, they immediately went into 'gimme' mode. So, I just stopped talking to them. Since it was everyone I knew, it was a long time before I had anyone to talk to.