I ate a Frosty at every Milwaukee Wendy’s location (2024)

If you’ve been to a Bucks game, you know the deal that happens after every victory. Yes, I’m referring to the “Bucks Win, You Win” deal at Wendy’s.

The deal will consist of a free small Frosty from participating Wendy’s locations following a Bucks’ win. It’s so engrained in Bucks culture that it flashed on the jumbotron just seconds after the team won the NBA Finals in 2021.

Given that we’re in the drought of the off-season before training camp begins soon, I had the idea — what if I tried to eat a Frosty at every Milwaukee Wendy’s location? Some might call it a terrible idea...others may call it, a horribly terrible idea.

This has actually been on my radar for a few years. If you’ve ever followed Tyler Maas of the Milwaukee Record, you may remember his story of eating at every Milwaukee Taco Bell. This provided some inspiration to this challenge.

Well, this past Saturday, my fiancé was away on her bachelorette party and I was home to watch our dogs. I ended up deciding that this would be the best chance for me to embark on this wild challenge.

I couldn’t go into this without getting some type of workout in. I took Daisy, our 1 ¹⁄₂ year-old Golden Retriever out for a three mile walk to start the day:

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And then, it was business. Here’s a timeline of how everything unfolded. I’m going to try not to vomit while typing this up.

10:19 AM: I start the trek from our house to the first Wendy’s. There are ten in the Milwaukee area. I took the addresses from the official Wendy’s site. I plot them in Maps and add stops along the way to be as efficient as possible. I decide to work my way from the northern locations down to the south side. I’m feeling ambitious, but know that I’m going to start hating myself in just over an hour.

10:48 AM: I arrive at the first Wendy’s location of the day (8331 W. Brown Deer Rd):

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11:01 AM: I decide to start the challenge with a chocolate Frosty. You can never go wrong with chocolate, so I thought that this was the only way to begin things. Since the deal gives away a free small Frosty, that’s the size I went with for each of my purchases:

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11:07 AM: I finish the first Frosty of the day. It went down with ease. It gave me a feeling that this could be easier than I thought, though I knew that wasn’t going to be the case:

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11:20 AM: I arrive at the second Wendy’s location of the day (11201 W. Silver Spring Dr.). I decide to try and switch things up and go with vanilla. Unfortunately, I’m told that they have just chocolate and triple berry. I decide to keep things going with another chocolate.

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11:27 AM: I finish my second Frosty of the day, resulting in the first cup snake of the challenge:

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11:38 AM: I arrive at the Wendy’s located on 6225 W. Capitol Drive. I glance at the drive thru menu. Indeed, they only have chocolate and triple berry flavors. Oh boy, I tell myself. I decide to try triple berry. This is either going to be a hit or miss.

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11:42 AM: I get my third Frosty. The guy in the window is wearing a Bucks Win, You Win shirt. I think about telling him the challenge I’m embarking on. Out of risk of embarrassment, I opt not to. A look at the first triple berry flavored Frosty of the day:

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11:47 AM: I finish the third Frosty of the challenge. Triple berry is not the way to go. It’s not bad, but in this scenario, it’s like mixing booze. I tell myself that I’m sticking to chocolate the rest of the way. This is also the first time that I hear my stomach rumble. Nervously, I head out of the parking lot and onto Frosty No. 4. Your cup snake update:

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11:57 AM: I pick up a second wind thanks to songs that came on my shuffle. Volcano by Jimmy Buffett and The Dream by Thee Oh Seas gets my mind in the right place again. I pull into the Wendy’s located at 4601 W. North Ave:

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I pull around the drive through with a regained sense of confidence. As soon as I order another chocolate Frosty, I’m told that their chocolate machine isn’t working. OH NO. This is where things get tough. I must resort to ordering another triple berry.

12:12 PM: I finish my fourth Frosty. That was definitely the longest it took me to finish one. I now head back to Capitol Drive for the halfway mark and am praying that their chocolate machine works. I cannot handle a third consecutive triple berry. Your snake cup update:

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12:23 PM: As a way to re-focus, I decide to resume an episode of one of my favorite podcasts, Stuff You Should Know. In the episode I’m listening to, they’re talking about the biggest mysteries on the Internet. I listen to them talk about the Most Mysterious Song on the Internet. Basically, nobody knows who or what band wrote it. It’s actually pretty interesting. Definitely recommend checking it out along with the Stuff You Should Know podcast.

12:26 PM: I arrive at the 2725 W. Capitol Drive location to five-plus cars clogging the drive thru lane. I’m grateful for this lunch hour rush, as it gives my stomach some time to settle. As I wait, I’m crossing my fingers that the chocolate machine is working at this location:

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12:46 PM: I finish my fifth Frosty. Thankfully, this location had chocolate. I’m officially at the halfway point. At this point, I’m sickened to say that the Frosty’s are just starting to blend together. I’m developing robotic motions that just make the ice cream disappear. I tell myself that once this is all done, I’m taking Daisy for another long walk. An update on the cup snake:

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12:51 PM: I arrive at the sixth Wendy’s of the day, also located on Capitol Drive:

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1:09 PM: I down Frosty No. 6. This is the point of the afternoon where my first brain freeze hits. I shake it off and gear myself up to the next one. Your empties update:

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1:22 PM: I pull into the seventh Wendy’s location of the day, which takes me back to North Avenue:

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1:35 PM: I inhale No. 7. Like I said, they’re just all blending in at this point. Another brain freeze hits me. I’m grateful that I didn’t order any chicken nuggets earlier in the day. I thought I might just to change things up and give my taste buds something different to consume, but am thankful I didn’t. I can see the light at the end of the tunnel. Three more Wendy’s and three more Frosty’s left. I begin the trek to the south side of Milwaukee. But first, a cup snake tally update:

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1:51 PM: I arrive at the Wendy’s located on Layton Avenue. At this point, I decide to go inside to:

a) Use the restroom
b) See if I can still walk

Thankfully, I can still walk. I also thought going inside would be a nice change of pace. I find that ordering inside takes longer than it has in the drive thru, but I’m not complaining. Rather, I welcome the break in the action.

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2:05 PM: As I’m eating my Frosty, I’m on the clock for one of my fantasy football drafts. Doing the research on what player to select helped take my mind off the calories I’m downing and gave me the concentration needed to finish not just this Frosty, but the remaining ones. Just two more left. Your snake cup update:

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2:19 PM: I pull into the ninth Wendy’s of the day, located on 43rd Street:

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2:29 PM: Frosty No. 9 is complete. At this point, I’m just determined to finish the challenge as quickly as possible. I’m taking as big of bites as possible to make things go faster. Probably not the smartest idea, but I just wanted to be done as soon as I could be. A cup update:

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2:45 PM: I head to my neighborhood Wendy’s in Bay View. I thought this was a nice one to end on. I never go to eat at Wendy’s, but thought it’d be fitting to finish in the area I call home:

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There it is. The last Frosty of the day. I think to myself that this has to be the first and only time somebody in Milwaukee has ever tried to do this ridiculous challenge.

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2:57 PM: DONE. I empty the last Frosty cup of the day. I did it. 10/10. Oddly, I did feel somewhat accomplished — but it wasn’t an accomplishment I’m exactly proud of, if that makes sense. But hey, I did it — and I hope you enjoyed it (and didn’t vomit while reading this). Your final snake cup tally with all ten Frosty empties:

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I then head home to let our dogs out. Thankfully, I hold true to my promise and take Daisy for a long evening walk of seven miles throughout Bay View. I get back and pretty much immediately get ready for bed.

So, yeah. I’m probably never going to have another Frosty at Wendy’s again, or at least for a very long time. It was a tough challenge, but honestly, I thought it was going to be tougher. But still, the taste of a Frosty is something that I’ll stay away from for quite a bit. I’ll also likely cringe every time I hear the Bucks Win, You Win promo announced at any future Bucks games.

And before you ask—no, I’m not going to eat a chili at every Milwaukee Wendy’s location.

I ate a Frosty at every Milwaukee Wendy’s location (2024)

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