Being Single Costs an Extra $2K a Year and Other Reasons You’re Poor

You took fake it till you make it too far.

We’re entering the summer months – which in Chicago is a very big deal. It’s that time where buying rounds of drinks (at every rooftop in the city) is important. We’re getting fake tans and taking yoga classes and getting the matching yoga pants that are trending on Instagram.

But before you start doing it for the gram (yes, we saw you throw out the Starbucks Unicorn Frappuccino), you might want to take some advice from the goddesses of being the plus one of the rich and the famous, Guest of a Guest. 

Guest of a Guest recently published a post detailing why you’re poor. They covered it all from Ubering every day (yes, it’s still cool to walk a few blocks, even in heels) to buying a name brand white t-shirt instead of the value pack at Target.

I did a double take when I saw that dating around can set you back an upwards of $2,000 a year. Ang then Guest of a Guest emphasized, “No, seriously, studies have demonstrated this.”

If you’re trying to save for a summer vacation and wondering why you have no funds to go somewhere and get an actual tan (Cabo, Meekanus, anyone?) then you need to stop what you’re doing and check yourself.

On the list (there are 13 reasons) included:

  • Buying name brand instead of bulk
  • Ubering everyday
  • Doing it for the gram
  • You’re single

For more financial advice, learn from this guru who talks about giving up Uber and brunch to save for bigger investments. 

Cheers for taking a moment to be financially savvy! No one will know that your white button down isn’t Burberry and if you’re staying at home drinking Barefoot wine and Netflix and Chilling instead of buying dinner for your next one night stand. We get it, you’re bad and boujee.




The Founder of OkCupid Talks Soulmates

Love. It’s in an algorithm. At least according to Sam Yagan, a mathematician who founded OkCupid.

Yagan and I met in the back room. As a serial entrepreneur, who is now investing his resources in Chicago, he gave an hour talk about entrepreneurship to a group of young professionals from Ivy, the social university. I said I appreciated the talk, but I was hoping to speak to him more about love and relationships.

He was agreeable, and I started talking with Yagan about the matters of the heart and how science can prove compatibility.

“Our match percentage is uncannily good,” Yagan said about OkCupid, a dating website which was started by four math majors. It works so that the more questions you answer (which should be about 100), the better your match percentage will lead you to someone compatible.

These dating questions range from asking about religion to asking about your level of cleanliness.

Dating Apps: How to Compete in the Game of Love

“I think each dating product has its own strengths,” Yagan said. He noted that dating apps like Tinder use your social network and attractiveness to find your companion. Later on, Yagan moved on to be the CEO of, when OkCupid was acquired by

Overall, his experience with founding startups has taught him that if a competitor is really good at one aspect of the business, then you cannot compete in the same industry at that level.

“You have to change the rules of the game. You can’t outmatch Match spends a lot of money on tv advertising,” Yagan divulged, “What OkCupid did was that we said we were going to be free. We started a blog that exposed vulnerabilities of our business. We became the reference brand of online dating because we had this data to share that didn’t.”

Average Looking and Dating:

During Yagan’s lecture, he emphasized the importance of starting a startup because you are trying to solve a problem.

So, it was only fair to ask him what problem he was solving by founding the dating site, OkCupid, “We believed we could predict compatibility using math.”

I liked that answer. We all have our lists of criteria that we want in our soulmate. And here, Yagan and his team were trying to use numbers instead of physical attractiveness and a meet cutes.

“Most people are average looking. That’s the definition of average,” Yagan went on about dating profiles, “With the match percentage, it gives you a reason to give someone a second chance or a first chance.”

After his dip in the dating apps and website business, Yagan has moved on which he considers similar to the experience of “when your kid goes to college, you know your kids want to leave the house. You don’t want your 26-year-old to live with you.”

With all of this data on love and relationships from his dating website, Yagan said that OkCupid broke barriers like height differences and racial barriers.

We concluded with that one question we have when we are dating – and that is – is there just one person out there for us – do we only have one soulmate?

Yagan smiled and said, “No.”


Don Your Victoria’s Secret Laciest During This Valentine’s Day Chicago Charity Run

Running outside (in the city!) in my Victoria’s Secret lace sounds a little extreme—extreme like the weather we tend to have in February.

No, no one is taking my clothes. But you and I might be rethinking them during Valentine’s Day  Victoria’s Secret sales.

With all of this extra sleepwear, what’s a single girl to do?

We brainstormed and slumber parties were totally part of the list. But, we thought we could use our Victoria’s Secret laciest to draw attention and raise funds for a greater good.

My friend, Maddy Osman (@MaddyOsman), created the answer: use your Victoria’s Secret sleepwear for charity this Valentine’s Day Weekend in Chicago’s Annual Cupid’s Undie Run.

I know you’ve been working out and need an excuse to show for your January New Year’s Resolution progress.

Lace and Other Details:

Running should be fun and nothing will give you a rush like running in your bedroom’s best.

The fun begins on Saturday, February 13, 2016, in Chicago.

  • Noon – Doors open & the party starts!
  • 1:00 PM – Awards ceremony
  • 2:00 PM – Cupid’s Undie Run
  • 3:30 PM – Earned “open bar” closes
  • 4:00 PM – Bag check closes, Cupid’s officially ends

Is There An Open Bar?

I tried to answer your most important questions first.

So, yes my Chicago cocktail queens and cosmo lovers, there will be an open bar. All you have to do is spread the word (aka share this article or bring up its contents during happy hour) and raise $250. Full Disclosure and Rewards for top charity fundraisers are here. 

What to Wear:

In all soberness, I wouldn’t wear lace to a race. But to each her own.

Chicago runners get creative and wear onesies or sport’s bras or as the name call’s for, underwear.

There is even Cupid’s Undie Run merchandise that you can purchase or use for inspiration.

Note: You don’t need to go shopping at Victoria’s Secret for this charity run.

Cupid's Undie Run Chicago 2016 Photo: Cupid's Undie Run

Cupid’s Undie Run Chicago 2016 Photo: Cupid’s Undie Run

Picture Everyone in What Room in Their Underwear?

You’ll be running in Wrigleyville. And trust me, Wrigleyville has seen crazier things than you and your underwear.

Starting at John Barleycorn (3524 N. Clark Street) you will run a lap around the under construction, Cub’s Stadium, as you enter the streets of Chicago’s most flamboyant and lively.

Cupid’s Undie Run Official Map

Going The Distance For Love:

It’s a brief run. BIG party.

You don’t have to walk 1,000 miles or even 500 miles. It’s one mile, babes. We can do it (though maybe not without a sports bra).

You, Me and Who?

Like the confident woman I know you are, you can run alone. But, you can also make it a group effort and raise money for Cupid’s Undie Run in Chicago by registering as a team.

And, no, Chicago isn’t the only city participating.

Cupid has expanded his reach and put the love spell on San Diego, Milwaukee, Virginia Beach, Miami and Salt Lake City,  Vancouver, Canada and Gold Coast, Australia.

Charity Run:

Feel like there’s no one who wants your love this Valentine’s Day Weekend? Think again.

The Children’s Tumor Foundation will benefit from your race donations. The Children’s Tumor Foundation is the world’s largest non-government organization dedicated to ending Neurofibromatosis (NF) through research.

The founders created this charity running event with a clothing optional twist for a reason:

We run in our undies because people with NF can’t cover up their tumors. They can’t put clothes on to feel more comfortable, so why should we?

Children with the genetic disorder, Neurofibromatosis (NF) develop tumors. These tumors lead to several problems including:

  • blindness
  • deafness
  • learning disabilities
  • severe chronic pain

$3.5 MILLION was raised last year for The Children’s Tumor Foundation.
Join the Fun and help double it for 2016!

P.S. Your company might match your charity donation!

Cupid’s Calling: Sign-up Now:

You may be wearing less, but you can save more if you sign-up early!

Register by February 5, 2016: $45

February 6, 2016 – Chicago Race Day: $55

P.S. All team members have to register individually, so just tell your friends your team name and they can choose it from the drop-down when they register.

An Extra Race Discount for my Windy City Cosmo Loves:

I don’t have a bow and arrow like cupid, but I do have a special EXTRA discount for you.

Get 10% off registration with code “CHICUR$”!

Bonus: It’s your first charity race of the year.

I just might be the girl in the pink robe this Valentine’s Day Weekend running down the streets of Chicago. Share the love and the Chicago event invite by tagging @WindyCityCosmo on Twitter, Instagram, and Facebook and use the hashtag: #EndNF.

Skimp On the Clothes, Not Your Charity Donation:

Windy City Cosmo will be racing this Saturday, February 13, 2016. Help support by donating here so we can help children like Kelsey, who has been fighting for her health and her life since 3 years old.

You can always, donate here to help The Children’s Tumor Foundation and keep the Victoria’s Secret lingerie and (how you look in them) to yourself.