Chicago Has the Most Existentially Miserable Men in America, Study Says

Travel Features America

My inbox is flooded daily with inane publicist emails that are completely meaningless to me, so it’s always a pleasure when I come across a message I can actually use. It happens rarely enough—once a month if I’m lucky—and it always comes in disguise.

For example, Amazon once sent me rock-solid proof that Knoxville is the saddest city in America, but the subject line of the email insisted it was the most romantic. It happened again when some awful dating website tried to claim that the University of Kansas had the country’s “hottest co-eds.” As the Sherlock Holmes of publicist emails, I quickly ascertained the truth—Kansas simply had the most desperate men.

I’m happy to report that after a month-long drought, I woke up this morning to find pure gold in my inbox, courtesy of a nice lady named Nicole, with the following subject line fairly screaming at me:

White Sox Fans are Most Generous Daters!

As with the Kansas debacle, it comes from an awful dating website—this one is called “,” and I’ll give them the floor as they describe their relatively satanic mission: is the only Sugar dating site that is redefining Sugar. Founded in 2014, the site aims to match like-minded individuals who are looking for a successful partner. is a Sugar dating site that promotes a certain lifestyle and honest, open relationships.

What’s that sensation I’m experiencing? Is that ants crawling all over my body? Or just an all-encompassing, full-body disgust the likes of which I’ve never felt before?

Just kidding, I’ve felt it before. This website is fairly standard—setting up sad and desperate rich men with poor, aspiring hotties (or vice versa?) in a digital monument to society’s worst gender stereotypes. Par for the course, basically.

But what’s all this about Chicago? That’s where the email went from ‘disheartening reminder of our collective failure’ to ‘vaguely interesting.’ We turn it back over to Nicole: wanted to discover which teams the most generous Sugar Daddies cheered for. internally polled 2,782 men, throughout the U.S., to find the top ten most popular MLB teams for Sugar Daddies, and asked users what they typically spent on dating activities each month.

Pardon me for a moment while I vomit after reading the words “Sugar Daddies” in that first sentence.

(Retches into special garbage can marked ‘Cloying Publicist Emails’)

Okay, I’m back. Well, there it is again. Just a moment.

(Retches into special garbage can marked ‘Publicist Overflow’)

Now, then. Where were we?

It turns out that men from Chicago (or “White Sox fans,” in this case, since Nicole sent me this email in my capacity as a sports writer), spend the most money per month on dates. Here’s the full list of average monthly expenses on dating, city by city:

1. Chicago White Sox – $4,231
2. Washington Nationals – $3,876
3. Seattle Mariners – $3,356
4. Los Angeles Angels – $3,164
5. Texas Rangers – $2,977
6. St. Louis Cardinals – $2,711
7. Boston Red Sox – $2,309
8. Milwaukee Brewers – $2,035
9. New York Yankees – $1,844
10. Colorado Rockies – $1,615

On the surface, this is disgusting. There are 31 days in most months, which means that the AVERAGE Chicago man is spending $136.48 every fucking night in dating expenses.

What an awful lifestyle that must be. Just finished a long, grueling Monday at work, and you want to chill with your lady and watch some House of Cards on the couch? NOPE: Find a place to spend $136.48, bucko. It’s a Tuesday in December and you’ve got the flu and an insane 45-mph wind is blowing off Lake Michigan, dropping the wind chill to -56 and also you’ve just broken both your ankles falling down a set of stairs after getting drunk on $136.48 worth of mojitos the night before? LEAVE YOUR HOME, SUGAR DADDY. FIND A LADY AND SPEND $136.48. THIS IS CHICAGO.

(Forgets rule about sugar daddy, retches into garbage can marked ‘Auxiliary Publicist Overflow’)

There are only two explanations for this data.

Explanation A. The numbers are total bullshit. However, reaching this conclusion would mean questioning the integrity of and the weirdos they called for this survey, and I wouldn’t dream of making such a leap. I’ve seen no evidence that OMT is anything less than an upstanding corporation (ie, person) dedicated to bringing a measure of happiness to those tragically under-served and overlooked demographics: Trust fund babies and gold diggers.

Explanation B. Chicago is full of existentially depressed men who have sunk to such levels of ennui-driven despair that their only recourse is to throw obscene amounts of money at life in the hopes of chasing down a brief, glimmering moment of happiness.

I find B to be the only compelling argument. And if we look at the cities in the top ten themselves, the facts of life back up the notion that they could produce these sorts of miserable, joy-deprived male citizens. Let’s go city by city:

1. Chicago: Cold and windy 11 months of the year, essentially uninhabitable, giant inferiority complex to New York. Literally known as “the second city.”

2. Washington: Headquarters of a broken political system, spearheading the rapid decline of one of our planet’s great civilizations. Full of superficial social climbers like Los Angeles, but not as attractive.

3. Seattle: Constantly raining, nationwide leader in suicides, second-coolest Pacific Northwest city (out of two total). Had to legalize weed to make life bearable, didn’t work.

4. Los Angeles: Headquarters of an entertainment industry that has destroyed America’s self-image and turned us into a loathsome nation of fame-obsessed couch potatoes. Full superficial social climbers like D.C., but not as smart.

5. Texas: I mean, come on.

6. St. Louis: Boring hub for Midwestern superiority complex, which is itself the ugly outward face of a deep self-hatred manifested city-wide by people whose lives are so aggressively dull that they’ve run out of other ways to cope.

7. Boston: Hotbed of leftover Irish immigrant rage mixed with delusions of grandeur mixed with the world’s ugliest accent mixed with virulent racism.

8. Milwaukee: See no. 6, but with twice the diabetes.

9. New York: Obviously a mistake, terrific city.

10. Colorado: Slowly, and legally, smoking themselves into oblivion. In one year they will no longer be on this list.

So there you have it: Chicago’s men are wretched sad-sacks. I’m happy to have resolved this mystery, and I thank for opening this important dialogue. Please give them a visit, especially if you’re a red-hot Sugar Daddy who—

(Curses self, retches all over desk and computer, makes note to buy fourth garbage can.)

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