I won some stuff in a church raffle when I was a teenager. Nothing remarkable - i think a suitcase.

I also won some sex toys from a charity raffle for repro rights, but some past partner took them. Not sure who, but I don’t have them anymore.

Thinking about it for the first time now, it is funny how those are two very different contexts.

I won on a radio call-in show called “name that tune,” three times. They took two callers. First one gets one second of music and time to answer. If they fail, the second gets ten seconds of music and time to answer.

I was in the one-second position all three times. I was sort of amazed that I kept winning. The prize was a CD in each game. That’s how I got into Stabbing Westward, as I wouldn’t have bought Whither, Blister, Burn and Peel myself, but it was a prize.

I was a volunteer working at the first LinuxCon in 2009, I worked in the expo hall and at the end of the first day one of the booths had a raffle to win an android G1 developer phone and I ended up winning.

The best part was, by winning the phone instead of having to buy it through t–mobile I was able to keep my service without having to pay for adding data and it was a couple years before I had to actually start paying for data.

When I was a kid my parents won some kind of sweepstakes or drawing. Well it was like third or fourth prize, but it was a huge box (a cube almost as tall as my legs are now) that was just filled with cereals.

A Kellogg’s contest, I believe. Can’t remember for sure.

I didn’t think anyone actually won Instagram contests, but my spouse won a magnum of locally roasted coffee which is lovely, and a free Valentine’s dinner at a very nice restaurant in Buffalo. I won a board game called Scruples for answering some ethics question in a column in the newspaper the Globe and Mail. Many years ago before it became what it is now.

I worked at Starbucks 25 years ago, when it was actually not a bad job and had some nice perks and was actually pretty good to work for. There was a game called Cranium that was sold through Starbucks then, and there was a contest for staff for a draw to win a VW bug with Cranium decals on it, and amazingly my coworker one, the decals could be removed. It was actually pretty nice.

When I was a kid we won second in a general mills national contest for “a treasure chest of games.” They sent us a cardboard board with plastic pieces and like 4 games on it. Someone sued based on the commercial, and we got some cereal coupons.

Many years later, I won like 3rd in a Mountain Dew cap contest. They actually sent me the snow board - no binding or anything, but Mountain Dew has integrity.

I somehow managed to get through to a radio show that was having a giveaway, and answered their question correctly. I won tickets to a concert, and a load of their sponsor’s merch. I was still young, but even then I knew my luck was shit, so I was really excited even though I didn’t like the band I was going to see lol

Didn’t matter.

The tickets arrived the day after the concert had happened, and the merch was all either factory seconds or used (so all slightly damaged in some way - a stain, an undone seam, a broken clasp). I tried calling to let them know, but all they did was send another load of damaged merch.

Off the top of my head, that’s the one and only thing I’ve ever won.

I really do have shit luck lol

Back in the mid 90’s, I won a “Rocko’s Modern Life,” t-shirt from a Nickelodeon contest. It was one where you’d have to call a phone # when his face would pop up in the bottom corner or something like that for like 10 seconds. Caller # whatever, could win the grand prize or whatever but I got a tee. Wore that shirt with pride all the fucking time.

Radio question. Sibling knew the answer, but didn’t want to call. Mother was driving. So I called. Have the answer. It was correct and I was the first. We won tickets to some young kids show and gave them to a family friend.

I also won a Weird Al lookalike contest. Despite being female. I was one of three people there and the only one trying. Which meant Hawaiian shirt, my old huge glasses, and permed my hair. Got front row tickets for that, which is all I wanted so my very short sibling could see the concert. Also got to meet him though, that was nice.

I got Drake’s leather diary from the uncharted games through a subway sweepstake.

Almost 20 years ago I won an iPod Nano and a Fubu shirt at a raffle at a black church in Norfolk VA when I was 17. I was the only white kid in there.

To say the bus ride back was uncomfortable is an understatement

Ahhh, I’ve won a goodly number of things.

Back in school, me and this one girl spent years going back and forth as spelling bee winners.

Won a watermelon seed spitting contest.

Jr high, I didn’t win shit except some bad memories, but that’s off topic lol.

High school, I took a couple of weightlifting wins.

After that, as an adult, it was more hit or miss. Never anything worth money, or not enough to matter.

I am still absurdly proud of winning a biscuit cookoff at the county fair. Not even joking, I was up against old southern ladies that had been making biscuits longer than my dad had been alive. I had been working on perfecting my recipe at that point for about ten years. I won that fucking ribbon twice. It’s all about technique, how you handle the dough.

While it was kinda low key, no prizes, no ribbons, nothing physical, I won a cross school sparring session at the dojo I went to. We cross trained with several other dojos of various arts. But the guy that owned our dojo got five of those to all get together and do this big session.

Basically, you go in and you spar. Light contact only, you have to protect your training partner. But you get in the circle and you go until you tap, or someone scores a hit that would be a KO. Next person steps in when that happens. I was taking classes in both Japanese jujutsu and American kempo. This was maybe a year into things, so I was still raw as hell.

We were in three groups, beginners, intermediate and advanced. I was thrown into intermediate. I can’t recall how many of us were there total. I wanna say it was a little over a dozen in that group, plus maybe twenty in the beginners, and a handful in advanced.

Anyway, I was third in. I did the full group. Got damn close to an actual KO when an axe kick was faster than I thought. Was damn near choked or otherwise close to tapping more than I can recall. I was breathing fire and eating bitter. Like, my throat was in more pain than anything else because it doesn’t matter how well you hydrate, you’re panting and struggling so hard it gets dry in seconds. And I had to pause twice to vomit, hence eating bitter lol. I can’t recall the japanese phrase for it.

Anyway, the first two guys cycled back in, and I managed to scrape out an arm bar and a leg lock. The circle starts again, and I’m wiped. Like, my arms are rubber, I’m dizzy and can’t see straight, I’m wobbling all over the place. I don’t even remember the last two guys. But the last one got me. Basically just pushed me over lol. I had nothing left in the tank. But I was the only one in any of the groups to go a full circle.

I have no clue where it came from. I’m not exactly Mr stamina. I was a power lifter, I wasn’t built for that kind of sustained effort. I damn sure didn’t manage the feat the next meetup lol. Did well, but not running the circle well.

But! I did get my dinner and drinks paid for out of it.

Later on, as a bouncer, I got into some real fights and some of those were way less of a “win” in my mind.

About the only thing I’ve ever won that came with enough money to amount to anything was a chili cookoff. Prize was a hundred for the winner. So, you know, not a big prize or anything. This was small time stuff. I did do some other cooking stuff at a state level, but never got wins. I spent that hundred on my nephew. He wanted a guitar, and had been saving. He had found one he liked at a pawn shop, and was short something like fifty bucks. So I gave him the hundred to finish it off and get some strings or whatever.

I won Blockbusters Donkey Kong tournament for the SNES when I was 6. Got a champions card that gave me one free video game rental every other week for a year. I won at two stores and my brother won in 3 stores in his age bracket. So we constantly had free new games to play. That was the best year ever.

Maybe fun fact: Dr. Disrepect’s “Two Time Champion” claim is from these blockbuster tournaments.

When I was still being taken to church I won the door prize at youth group (church for teens) one night during a special event we were running (some thing to encourage people to invite their non-believing school friends and show how “hip” and “fun” they were, there were raffles and video games alongside our usual “live music”, skate ramps and bbq). The prize itself was a mobile phone. I was so happy because I didn’t already have one, but ultimately my parents decided I couldn’t have/use it until I got a job to pay for the credit. I did eventually get a job at KFC and was able to use the phone.

Another time I was visiting NZ with my parents and we were touring the base of a mountain and the guide was like “guess the height and whoever gets closest wins this pen”, I won but my mum made me give the pen back because she thought I’d cheated somehow? Idfk. Still a bit salty about the pen.

We had a raffle at the local community center. Everyone bought tickets, and the prizes seemed decent (bottle of wine, large wicker chair, rocking horse). The winner of all three draws was the long-standing cleaning lady of the center, who had just had a grandchild and was heading for retirement.

I’m all for supporting someone’s retirement, especially for someone who has given a lot of effort to making the community feel hospitable.
But not like this, not like this…