About twenty iPods.

Walkers, a snack company, was running a contest where you could enter a draw every ten minutes, 24 hours a day, to win an iPod. They also had a website where you could get an entry code without buying anything. I was one of the few people to have unlimited texts and a phone controllable by Bluetooth at the time, so I ran a script to just spam the free entry codes. Somehow they never cottoned on.

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 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.

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.

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.

When the internet was still young I entered an online drawing to win a vacation on a travel website. I never really thought much of it. One day I decided to answer the phone even though we got lots of telemarketers. The woman was from the travel company and said I’d won a rafting trip in CO and that this had been their third and final attempt to reach me. It was totally legit, they paid for the flight, rafting trip and rental car. Due to low river levels the trip was moved to the San Juan river in UT though. It was an awesome trip. We even paid some extra to keep the rental car longer to add some extra sightseeing days to the trip.

Around 1981 or 82, I was about 12 years old and the local college radio station had a call-in for identifying snips of popular songs at the time. Best I can recall, it was Girls by Dwight Twilly, Let the Music Play by Shannon, and I think there were 3 others but I can’t remember what they were. The prize was a discount coupon to the local pizza place.

I won a geolocation game from Rita’s and got a year of free Italian Ices. Every day during March they gave out a geolocation and you had a certain amount of time to find them to win. The first few days i missed the time limit. A couple times i was second. After a week or so i noticed a general pattern and started closer to the part of town i thought they would be. The day i won i was in the parking lot of the stadium where they were and watched them setting up. as soon as they sent out the geolocation i walked up and claimed my prize.

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

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 won a robot R2D2 in a raffle. This was like over 10 years ago. It had voice commands, and somehow understood me better than Siri.

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.

On my 18th birthday I bought 2 scratch lottery tickets, and doubled my money (20EUR spend, 40EUR return). Never played since. I beat the system 😎