What do you do when you’ve turned into Carrie Bradshaw?

“Are you a player?” he asked me as we walked down the street.

“No, I just crush a lot,” I smiled.

I went home alone that night and I called my friend. “I only date players,” I said.

“You’re the biggest player I know,” she told me with no hesitation.

No. No, no, no, no. I can’t be a player.

The word “player” has such a negative connotation. It means he’s leading you on — he’s acting like he’s more interested in you than he really is.

A player is also someone who’s dating you and multiple other people at the same time. But because the relationship isn’t “real,” or defined, you can’t consider it cheating.

A player is cheating the system; they’re playing the game.

When I first started using Tinder, I loved how guys were always ready for a Tuesday night date.

You could swipe right in one second and your date would be waiting for you at a local bar just a couple hours later.

It was easy and simple, and it made the whole question of compatibility easy to distinguish. You actually met the person right away.

Going on a Tinder/Bumble/DM date was like eating a taco on taco Tuesday. It was convenient, it was fun and it was socially acceptable.

But after a while, you take a break from tacos and you come back and sit and wait and eventually think about getting more tacos. But no one asks you to go get tacos when you want them to.

When you start to date people, they could be seeing someone else. You know it and I know it, this isn’t your first taco.

There’s no rule book for when it’s inappropriate or hurtful to go on dates with someone else throughout the dating process.

Read the full article on Elite Daily.


Friendsgiving with Chicago Bloggers

Ahhh Thanksgiving. It is by far my favorite holiday because I love Thanksgiving dinner. Turkey, mashed potatoes, green bean casserole – and then of course apple pie.

Beyond the food, I love that there’s a new rush in the air to think about what we’re thankful for and then also what we want to give to others for Christmas and then goals we want to set for ourselves for the next year. Thanksgiving begins the season of joy and reflection. 

One of my favorite parts of Thanksgiving is Friendsgiving. It allows us to appreciate our friends and also learn how to, at the very least make a side dish. 

This year, I had Thanksgiving at the Dollhouse with two other Chicago bloggers from Once Upon a Dollhouse and their friends and family.

We had the whole meal catered by amazing restaurants like Maggiano’s – yes I put spaghetti and meatballs on my Thanksgiving plate. 

Besides learning that red wine or champagne are really the only appropriate beverages to complement Thanksgiving dinner, it was fun to meet other people’s best friends and talk about new beauty trends like tattooing your eyebrows, or swapping travel adventures to Thailand and Paris.

From Windy City Cosmo, I hope you and your friends and family have a beautiful Thanksgiving. I’m in Los Angeles for the second annual tradition. How do you celebrate the holiday?


How it feels to experience a sunny day in Seattle

When you wake up and go outside and it’s sunny in Seattle – you can’t help but smile. You meander through the streets and see the sunlight peaking out and you immediately walk towards the warmth. 

I recently took my first trip to the Pacific Northwest and after one day of the rain and cold, I couldn’t rationalize my move from Florida to Chicago. How did Chicago’s weather not affect me so much?

Seattle was so perfect, but I couldn’t get past the weather. It was like Chinese torture because it would rain. Stop. Rain again. Stop. Rain some more. And then freeze. 

Seattle is not a city of umbrellas, just baseball caps and jackets.

Seattle is gorgeous in its own right. It has so many coffee shops because without them everyone would be curled up in bed all day with a book. 

The locals don’t fight the weather. They have a positive mindset and smile and take your order or give you directions. But they have a sense of humor. They aren’t just nice, they are sarcastic and real. 

So as I took in the sunshine, I wanted to share with you how it feels to experience a sunny day in Seattle.

I am currently at the bay, experiencing the abstract art at Olympic Sculpture Park. I found a break in the path that led to a small rocky beachside. I like sitting on the rocks watching sea otters flip through the waves. I like hearing the waves so close to me as I sit on a big uncomfortable rock.

I like seeing the sun through the clouds and then feeeling it’s brightness on my eyes and it’s warmth on my legs as I recover from the chills of the storm – or as most would see it – an average day in Seattle.

I like looking out and seeing big white, puffy clouds and rich green grass. I like smelling firewood. I like getting excited about having coffee in the morning and stumbling upon all those places I’ve read about.

I like feeling the excitement and hearing the chants after a Seahawks game and seeing everyone wearing a shirt and an old man talking about his season passes

I did like taking a ferry to an island and talking to the girl with purple hair who gave me crab risotto on a gloomy day. 

I like books stores. I like activism. 

I like the intellectual conversation. I like the causal, but cool style.

But I like that when it’s sunny in Seattle, I can climb up the streets and down them.

I can walk up the residential streets of Queen Ann to Kerry Park and look over at a sunny Seattle.

I like continuing my journey to the Space Needle and though, not impressive, the surrounding pop art museum and science museum and the Chihuly gardens and the fountain were all worth the visit on a sunny day in Seattle.

I like sitting in the living room at 6 am to read the New York Times and look out and over to see the sun rise. I like staying in a mansion on top of a hill where I can walk to one of the most picturesque parks – Volunteer Park, where you can climb up a tower to see the sunrise and then climb down and sit on a sculpture and lookout around the surrounding forest and blocked off water.

I like art. I like the man painting a mural on a Monday morning. And most importantly I like taking a moment to be happy to see the sun. To smile and go to the bridge and lookout over a new city.

I really do like to explore. And yes I like to relax at night or on a beach and do absolutely nothing. But I really liked walking 29 miles in 48 hours to see the man painting a sculpture or the other man eating a Washington apple or the men throwing salmon at Pike Place Market.


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 Match.com, when OkCupid was acquired by Match.com.

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.com. 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 Match.com 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.”


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, he means the one who is sitting next to him. Because this is her date. I’m just here for the cosmo and moral support.

We finished our drinks at the bar, and then we got a table.

I went to look at the sunset and give them some space. But, after 15 minutes, I came back, and there we were, the three of us, still doing this.

So, what is this?

Is it cool to bring a friend on a date?

In the era of swiping, texting, and speed dating via apps, some of us feel it necessary to make these “hangout session” less formal and more informal. (But seriously how can you be more informal than Netflix and chill? I mean I’m looking at my last two dates that showed up in sweatpants.)

After we finished the calamari, and the man of the hour had an allergic reaction (don’t worry, not like in Hitch), my friend took his hand and walked with him to Walgreens.

My work here as the third wheel, was done.

To say, that this was my first time in one of these dynamics would be a lie. I think it’s natural to bring a Tinder date to a party or event, but sometimes that seems like too much pressure for a first date.You don’t want to be that girl that always has a different man with you on weekdays. Am I supposed to introduce you to all of my friends when I don’t even know exactly what you look like or who you are? More importantly, how am I supposed to find you?

I did it once during St. Patrick’s Day. I invited a guy to hangout with my group of friends and have drinks at Rock Bottom. It was actually one of my favorite dating stories.

But then there was this time I invited a guy to meetup with me and my friends. And then, we went to a bar and hung out with his friends. The night continued to another bar where his best friend hung out with us all night. It got to the point where I felt like I had to find another date because it felt like the two of them were inseparable. And, on my own date I felt more like the third wheel. So, I did what any girl would do. I walked out of the bar to go home, and they ran out after me. But wait, his friend took us back to my place.

How comfortable is too comfortable on a date?

I think it’s important to be comfortable on a date. You shouldn’t wear that tight dress you can’t breathe in.

But sweatpants? No.

Asking for dinner on a Netflix and Chill date? No.

Bringing a third wheel? I’m going to say no.

It’s nice to get a free cosmo on a date and have no obligation to talk to the guy again because he’s not your date, but it’s weird. It is.

Not to mention, what if you both like the guy.

I talked with a few friends at a cocktail party about it and they do the same thing. My friend brings her gay best friend with her on dates. He gets free drinks and she feels more comfortable.

There’s always a tug of war between the best friend the guy you are seeing. I tend to keep the men I’m dating private because we never reached a point for us to actually be an item.

But what are your thoughts? Are you team three is company or three is a crowd?











Amanda Elliott is a writer and speaker and a relationship builder. She believes that meeting people in person is important. After attending numerous fashion, startup, and creative events, she founded Windy City Cosmo is 2015 to help people make connections in the city as they build their businesses, start and end relationships and see and be seen. Over the past three years, the entrepreneurs she’s interviewed have become the most successful in Chicago and Windy City Cosmo won an award in 2017 for her work for female entrepreneurs.