I have never won a damn thing in my entire life. I also don't enter contests but if I did I still would not win.
Well no wonder you have never won anything, you have to enter in the first place! You gotta have a positive attitude about it, like I'm going to win this, I have just as good a chance as anybody else! Giveaways from magazines are the easiest to win, since I think hardly anybody ever enters those, plus they don't cost anything but a little time. Try it, you'll win something!
I've won quite a few things. What I remember at this time, are a trip to the carribean about 8 years ago, a VCR at my high school graduation almost 15 years ago, a 3 foot tall Tootsie-Roll bank at a costume contest when I was 5 or so, and a mini Indy race-car (a go-cart type thing) that I won in Jr. High. I sold it for $700 and my parents made me share the money (60-40% split) with my sister. I was pissed.
I have won two big prizes in my life. In college I won a airfare and hotel in Disneyworld along with $300 and tickets to the parks. That was fun because I was so poor at the time!
2 years ago, two days after I returned home from the hospital after giving birth to my youngest son, I received a call from Rockport shoes telling me I had won 2nd prize in a sweepstakes (I was waiting to pay for something at Lazarus and put my name in the sweepstakes box 3 times while I was waiting). They told me I had won a Piaggio scooter (I had no idea what a Piaggio scooter even was-I thought it was like a $100 Razor scooter). Come to find out it was worth $2300 and was just like a Vespa! I cracked up trying to picture myself (five days postpartum) riding on this scooter-I live in Ohio and have never ever seen anyone riding this kind of scooter. The woman from Rockport ended up offerring to just give me cash when she found out I had three kids-I ended up getting $2300 in cash when it was all said and done!
I won 10 free burritos from Chipotle. Woo Hoo! I shared them with my coworkers.
Also, I once won the door prize at a bar - a cd by a hip hop group I have never heard of...I never even listened to it, so I don't know if they are any good. My sister won a giant novelty comb at the same bar. I sort of wished I'd won that one instead.