Is it a date when you bring a friend?

I walked up to the bar. There was a cosmopolitan freshly poured. As I went to pull out my chair, he said, “We’ve been waiting for you.” And yes, I mean “we”. We were on the roofop at the Godfrey Hotel, a respectable place for a first date in Chicago. “Your friend has told me a lot about you,” he went on. And by my friend, … Continue reading Is it a date when you bring a friend?

The Relationship App Every Successful City Girl Needs

It’s not every day that women admit that they need help. But cocktails with the girls usually turns to talking about men, and we all know the casual questions that lead to excessive Tequila shots later. Who are you seeing? What dating app are you on? I wish this was cliché, but in my first night out this weekend, it was true for both my … Continue reading The Relationship App Every Successful City Girl Needs

When is the Super Bowl? I’m Not Single.

“I’ve been putting myself out there,” I told my friend “I’ve been going to dinner parties and museums, and I have only met gay guys,” I went on. “That’s because straight men don’t want to comment on centerpieces. Single men go to concerts and sports bars,” she divulged. “Oh, I don’t go to any of those,” I sighed. —- Super Bowl 50 Details: We’ve concluded … Continue reading When is the Super Bowl? I’m Not Single.

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

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. … Continue reading Don Your Victoria’s Secret Laciest During This Valentine’s Day Chicago Charity Run

Why You Will Fall In Love With The Guy Who Won’t Check All The Boxes

Today is an exciting day. Windy City Cosmo is featured on Elite Daily, an online publication written by Millennials for Millennials to give you the voice of Generation Y. This year, as I finish writing my book, Blow Me Away: Dating in the Windy City, I will be sharing posts with you about finding love in the city, date night stories, and book reviews focusing … Continue reading Why You Will Fall In Love With The Guy Who Won’t Check All The Boxes

Earls New City Adds a Holiday Spin to Happy Hour

I know what you have been wondering, why doesn’t Earls have an apostrophe? Earls Kitchen + Bar Lincoln Park  (1538 North Clybourn) is a family-owned Canadian business named after generations of men whose middle names are Earl. So, the restaurant is named from a group of Earls. Now that we have pushed grammatical queries to the side, let me introduce you to a Canadian upscale … Continue reading Earls New City Adds a Holiday Spin to Happy Hour

Do you lie when you meet someone new?

Do You Lie Within the First Ten Minutes?

They say that you are more likely to lie within the first 10 minutes of meeting someone new. After exiting the bus, a man approached me and began to walk alongside me. “Hi. My name’s Charlie. What’s yours?” I think to myself,  “Should I give him my real—” “Amanda,” my voice blurts out. He touched me ever so slightly, “Ladies walk on the inside.” “Have you … Continue reading Do You Lie Within the First Ten Minutes?

City Dating: Making Plans with a Flaky Man

He’s Flakier Than a Croissant

There are 24 hours in a day. So, when you say, “let’s hangout on Sunday,” please allude to brunch or dinner. P.S. who hangs out on Sunday night? Moving on. Men are notorious for a) making a vague reference to hanging out on one day sans a specific time, and b) not following thru. Dating in the city is interesting. It’s easy to get a guy’s attention, … Continue reading He’s Flakier Than a Croissant