My brother entered contests all the time as a kid, but he didn't win and he got discouraged and today he has the attitude of 'we never win anything and we never will'...well, my luck hasn't been quite like his.
The one victory I'm really proud of, I was not the first prize winner, I was one of about 100 first runners up, 9 years ago Nickelodeon had a contest called Nick-Or-Treat, you printed out entry forms, mailed them in, if they drew yours, they'd call your house and if you said 'Nick or Treat', you won 2 boxes of Hershey bars, and I did, I won 2 cases which I guess makes 62, I was so thrilled when they came! But my brother always brushed that off saying since it wasn't 1st prize it didn't really count, it sure as hell did to me, we all loved the candy!
These days I don't find too much stuff to enter but anything I do find I do enter for, and even though I haven't had much luck winning lately, that doesn't mean I won't. How about everyone else here? Do you enter and have you ever won?