I'm not exactly prone to winning things - but I do have one glorious moment of winnerhood that really is all I need in life. As a child, my church would throw Halloween parties every year.

One year, I was handed a raffle ticket along with my trick-or-treat candy. At the end of the night, ticket numbers were called - mine was the last one called. I still didn't know what the prize was.

Once I made it up to the stage to collect it, I was presented with a box of puppies and prompty LOST MY TEN YEAR OLD MIND. I thought I was just going to cuddle them, but nope! I got to pick out my brother and my best friend for the next decade.

We named our little box puppy Bear not knowing he would grow up to be a massive doberman who weighed triple digits.

My very favorite picture of my brother is him during what we call "the Ginuwine era." He's standing next to Bear wearing an Auntie Anne's Pretzel t-shirt and it looks like a ridiculous 90's r&b album cover. I haven't really won anything since winning Bear, but c'mon... that one win was enough. One Reddit user asked:

Sweepstakes winners of Reddit, what sweepstakes did you win and was it all that you hoped for?

Spoiler Alert: a Halloween puppy in a box is still the best prize ever - but some of these are pretty decent.



Short story time: I once won a contest for HotWheels. It might've been a regional thing, I'm not sure. But it was 1999/2000. And my local WalMart had a display of HotWheels at the front of the store, with special sheets of paper and entry forms for a contest - Draw your own HotWheels car, and win the full year's collection of cars (it was like 200 cars!). I was 13, and hadn't even bought a HotWheels toy since I was like 8. But whatever, I thought it would've been fun.

I LOVED drawing (I stuck with it, and grew up to be a designer/illustrator, now in my 30s), so drawing a sweet car would be a piece of cake. I drew some kind of rocket powered dune buggy, with multiple views, and technical specs, and I even named it - "Dune-n-Zoom" or something cheesy like that. I mailed it in, and forgot about it.

About 2 months later, I get a letter saying I'd won! The year's HotWheels collection was mine! I just had to fill out some more contact info on their forms, and short questionnaire. Did so honestly, and mailed it back.

And only 4 days later, I got another letter, saying I was disqualified. I was 13, and the contest was only open to kids 5 - 12. So I didn't win the car collection. Got my first taste of the ugly side of Terms and Conditions that year. Still bummed about it.

- Gavinardo

Graduate Heaven

Was a broke grad student who won free Chipotle for a year, and the same year I had free sandwiches for a year from another place.

Basically yeah, I was happy as hell.

- Enzohere

So Much Marijuana


Someone I'm close to won a trip to California (big deal in our little town in Ky) for a music festival. They flew her and her husband out, took care of their hotel and food, and gave them $500 in spending money plus tons of other merchandise. The girl who won has intense Gastroparesis. Basically her stomach is paralyzed, she can't eat, and it's unbearably painful. The only thing that helps her? Marijuana. When she can't work and money is tight, most of her weed is given to her and it's not very good.

They gave them hundreds and hundreds of dollars worth of GREAT weed.

She said it was the best week of her life. She actually got to go on a trip where she could smoke legally and enjoy herself without being doubled over in pain.

- heidivirginia

Chili And The Amish

I almost never win things. I've won something two times in my life, one of which was a few weeks ago.

There was a fall festival that had a chili bar, where each bowl you buy gives you 2 raffle tickets in a prize drawing. The prizes were mostly food or gift certificates.

Well I paid for my bowl and two bowls up front for my wife since she wanted to try different things. They went ahead and gave me all the tickets, so I had 6 total. Then my wife went back for her second bowl, which the lady remembered I had paid for but she gave my wife two tickets for that bowl anyway.. so now we have 8 tickets.

We also got 2 tickets just for coming, apparently everyone got them.. so we had 10 tickets total. I ended up winning a gift basket full of food from a local Amish store. We still haven't finished it all!

- Journey_of_Design


Worked for a local shoe store my last year of undergrad. TOMS did a contest for multiple companies and when you sold their shoes, X amount of shoes gave you X number of your name put into a drawing. Needless to say I sold the hell out of Toms that month.

Got a call from California at the store one night (live in Indiana) and both my manager and myself lost it when it was a rep from TOMS calling to let me know I had won.

All expenses paid trip to LA with 5 other people representing their respective companies to hang out and learn more about Toms. Badass hotel overlooking a bay, free shoes and shirts, free meals at great restaurants with drinks pretty much anywhere we went. Got to be there for the "Day Without Shoes" where we were with a few celebrities.

Needless to say it was a pretty great, long weekend - pretty awesome company and I've been a supporter ever since.

- hartleyja

Just 10 Gallons


I've won movie tickets on the radio a few times, but my mom once won a sweepstakes for 'free gas for a year'. It was actually 10 gallons of gas a week for a year, so it wasn't completely free. Just 10 gallons a week.

- partofbreakfast

Thanks Grandma! 

In 7th grade my grandma entered me in a sweepstakes to win a vip experience for the Pittsburgh Penguins from my local newspaper and I won. It was amazing I got to sit in the penalty box during warm ups, stand on the ice during the national anthem, meet a couple players, got signed puck and some other gifts, and amazing seats. Definitely the coolest thing I've ever won.

- shafferrr12

The Cracker Barrel Treasure

Early 80's, kid me entered random contest at the neighborhood Cracker Barrel. A year or so later got a 1oz solid gold coin in the mail. Not very exciting. I didn't even remember entering the contest.

I still have the coin in a safety deposit box

- thatguydrinksbeer

Waiting For Ariana


On a whim I entered into a sweepstakes for Ariana Grande tickets and meet and greet. Didn't think I'd win, but I did. The meet and greet was a joke, 1 1/2 hours of waiting for about 2 minutes of seeing her, and the concert was so bad we walked out of it after a handful of songs.

- Austifox

How Many Kids

I won $100 gift certificate to Toys R Us. I called our local shelter and asked how many kids they had. I can't remember the number now, but I went into Toys R Us and asked the manager if they could help. So I bought the exact number of boys a matchbox car, and the exact number of girls a small stuffed animal. The only disappointing thing about it was that because of privacy policies, they didn't allow me to actually give the kids the toys. I had to trust the shelter staff would give them out on my behalf.

That was a good day.

- cameramanlady

Jeep Grand Cherokee

My Parents won a Jeep Grand Cherokee in a raffle in the mid 90's.

I got to use it as my first car in the early 2000's. Complete junker at that point, but it was still my car. It had a problem where the gear would get stuck between park and reverse. It actually once rolled out of the garage and hit a bunch of trees. Not a good situation. Also happened to me while I was trying to get to second base with Mary. So year the Jeep Grand Cherokee proved to be a great cock blocker.

By the time it was no longer my car, the door hinge had rusted away, and I had to duct tape it shut and jump out of the window duke's of hazard style.

Good times, it actually got donated to a high school for repair practice.

- ooo-ooo-oooyea

The Accordion Fold


My aunt used to enter sweeps as a hobby. She worked off a sweepstakes newsletter and entered a few every morning. She has won a car, an above ground pool, countless trips including to Italy and Hawaii, lesser prizes like golf clubs, t shirts, hats. She won many tickets to Broadway shows, movies, concerts, cash. I remember when my daughter was a teenager she got a huge box of full size beauty products and makeup that my aunt won for her. So she was a lucky person in that respect.

However her husband died at 41 leaving her to raise four kids alone. So lucky? No. Did it make her hard life happier? Yes she loved getting the mail each day to see if she had any wins.

I'll share a trick she swore by. When filling out a card with your info that gets thrown in a drop-in box always accordion fold your entry. Then the person picking the winner has more "surface " to grab and it increases the chance you will be picked.

- grannygogo

3 Days Later

Entered one of those contests as a kid where I had to buy $X worth of product to qualify, then fill in a participation form and mail it to the company.

Won a bicycle, claimed it and parked it outside my house.

It was stolen 3 days later. I didn't even get to ride on it once.

- Towel_of_Babel

Had I Taken Someone Else...

I won a trip for 2 to Vegas to see an absolute legend in concert. Airfare and hotel accommodations were paid for, and it included backstage passes and a meet-and-greet. Food was the killer expense, the tickets were in the nosebleed section, and I took someone who I really regretted inviting, so the trip as a whole kinda sucked. But, I got an autograph and photos with the artist, and the concert was amazing. I also got a real kick out of taking photos from the stage looking into the crowd right before the show started.

The prize itself was all I'd hoped for - the free time wasn't. Had I taken someone else or gone alone it would have been a million times better.

- Erin42

No Thanks


I called in and won a pair of crocs from a local radio station. Needless to say, I never picked them up.

- giraffe111


Won 2 tickets to a UFC fight in Vegas (was living there). None of my best friends could go. My ex-wife suggested that I take "Jim", a friend in our group who had recently moved to town. He ended up bragging the whole time about him screwing all of the girls in my wife's circle but always adds the comment, "...except for your wife, of course!"

Found out shortly thereafter that they were in a month's long affair. Still bugs me 15 yrs later that she encouraged me to hang out with her lover. F*cked up chick. Turned out to be the tip of the iceberg.

- mowtown1

The Blushing Bride

My sister won her wedding dress. It was a contest on Facebook with a traveling wedding dress sale. One of the conditions of winning her dress was working the day of the dress sale. I worked the event with her as well as the other girls in the bridal party. It was a lot of fun actually, she got to choose her dress before the event started (worth 800$ at the sale, much more retail), and the woman running it liked how well we worked she paid us each 50$ which we didn't expect.

- readersanon

Red Power Ranger


When I was about 8 or 9 I think Toys"R"Us was doing lottery for a life size red power ranger that talked when you pushed the symbol on his chest. My family ended up winning and thought it would be a good idea to put it in me and my younger brothers room but turns out a 5'8" man standing in the corner of your room is scary for children. It ended up in the basement but became a wonderful Halloween decoration to this day. 10/10 would win red power ranger again.

- trap266


When I was a kid I won a draw for a free birthday party at my favorite restaurant!

Unfortunately I had written my birthdate (07/04) in dd/mm, and they read it in mm/dd, so they called in June.

They told me to call back in March and they would give it to me, so I did and they had forgotten :(

- 420shadesofgreen

Change Of Plan


I won 4 tickets to a movie at the IMAX theater from a spin the wheel type contest.

Went to the theater to get the tickets. When I realized that these tickets were not zero out and are showing the full price on them. Ask my friend to try and return them since we had an hour before the movie started.

They have us back like $55, so we all took off brought a bunch of beer and like two grams of weed.

- Darkone06

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