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.


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 Saturday night chatter at the J. Parker  with friends and during a Sunday media brunch at Osteria La Madia.

Successful Women with Dating Problems:

We all have a life or are “working on ourselves.”

We are doing yoga, our jobs are better than average and so is our skin at this age. But why is it that we are always mentioning Brad from next door or sharing Bumble profiles and Tinder dating stories over our mimosas?

Well someone decided to do something about these routine conversations—make a relationship app at 1871, Chicago’s tech mecca.

LUV TALK Co-Founder, Gwen Washington, a thirty-something Chicago city girl with a background in counseling, has pulled together a team of fashion stylists, therapists, and (divorce) lawyers, or as she likes to call them “gurus,” to answer love’s toughest questions.

The gurus specialize in various age to help with relationships and life tips. The relationship app will allow a private mini session with the guru to ask anything you want.

Who Do You Go To For Relationship Advice?

So, who do you go to for dating advice?

“People laugh and say, ‘Google,'” says Washington, who found herself helping her friends with relationship advice.

“There’s a lot of ways to meet people, but when you meet them, what do you do?” Washington asks.

Every girl knows this dilemma. I was talking with a new guy once and my friend looked over at my messages.

“You sound too direct.”

“Be flirtatious.”

“Wait a few minutes to respond.”

“Are you wearing that on your date? Let me help you.”

I found myself not knowing I needed help, when I did.

In the dating world, saying what you want when you want to and just being you, doesn’t really work. It’s not playing games, it’s just dating.

“Women need relationship advice more than men, ” said Washington,”I think the most important thing in finding the one is [to] find someone that makes your life better and you can’t imagine being without.”

Developing a Relationship App: The Details:

LUV TALK is Washington’s first app.

And like most Chicago app developers, she found a void and is seeking to fill it.

To do this, Washington put together a diverse app team not only ethically, but also in terms of their relationship status, to help her build the LUV TALK relationship app.

The LUV TALK team will be moving into 1871 this spring to develop the app for a summer launch.

It will originally target single women or those in relationships in Chicago and then move into larger markets.

But, her team isn’t the only place that she is gaining insights and data for the relationship app.

She has also partnered with a friend’s meetup group in Chicago to gain insight from focus groups.

Calling All Single City Ladies:

Currently in the data research stage, Washington’s app idea, LUV TALK, is available in the desktop version for Chicago single women to start asking questions on forums.

If you want to be more involved, Washington is holding a LUV TALK Ladies Event over bottles of wine at Tango Sur (3763 Southport Ave.) in Lakeview on Saturday, March 19, 2016. You can RSVP directly on Facebook or by emailing:

LUV TALK Relationship App Launch Party:

Washington’s app will be available later this summer on Saturday, June 11, 2016,  at a launch party at the Public Hotel. For ticket information for the LUV TALK app launch party, click here.





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 that if your winter has been more Hulu and Isolation instead of Netflix and Chill, you should make plans to attend a Super Bowl party (which is this Sunday, February 7, 2016).

P.S. The Denver Bronco’s are playing the Carolina Panther’s in this year’s 50th (no Roman numerals this time) Super Bowl.

You can still go just for the Super Bowl commercials which are $5 million for a 30-second spot. You can also go for the Super Bowl Half-Time Show with Coldplay, Bruno Mars, and Beyonce. Yes, Beyonce is back.

Kick-off is at 5:30 pm on CBS.

Bonus: The weather is going to be perfect compared to last year – no precipitation and a high of 43 degrees.

Where to Watch the Super Bowl:

Chicago is the best sports town. We turn into a college campus with pride and support for our Chicago sport’s teams.

Chicago Eater put together a comprehensive map of places throughout Chicago to watch the Super Bowl. 

Below are a few options for the sport’s fan, the Chicago foodies, the rooftop lover, and your average meetup.

The True Sporting Experience:

Timothy O’Toole’s Pub

Address: 622 N. Fairbanks Court

Super Bowl Sunday

This is one of my favorite bars for holidays. People show up —a lot of people show up here for a good time. They get decked out for holidays like no other Chicago bar. I expect the Super Bowl 50 to be no exception.

Specials include:$4.50 Miller Lite/Coors Light Stadium Cups, Jameson Shots $6.50, O’Toole’s Vodka Cocktails $6, Panthers Shots – $5

Bonus: Super Bowl Squares and scratch cards to win prizes every quarter. Flat screen TV Giveaway.

Bub City

Address: 435 N. Clark St.

Reservations recommended. 5:00 pm – 12:00 am

I love this place. It’s definitely a sport’s bar with a country flare. It’s trendy, it’s in a great location, and Bub City already has the 16 flat-screen TVs. I just hope you like Whiskey and southern food i.e. pulled pork nachos, Carolina pulled pork sandwiches, and hot, sticky, and sweet wings.

Stretch Bar & Grill

Show up for the game. Enjoy specials: $15 domestic buckets, $5 mimosa’s and bloody mary’s, Half-price bombs.

Bonus: Each shot you purchase gets you a raffle ticket to win a Bear’s jersey at the Super Bowl Halftime or at the end of the game.

Super Bowl Packages:

Bar Toma

Address: 110 E Pearson St.

Tickets: $30 per person starting at 5:00 pm to the end of game

Bar Toma_1

Bar Toma is excited to play host for the first time this year. With 22 big screen TVs and your bar food of wings, S’mores pizza, and more elevated by Chef Tony Mantuano’s, it’s going to be a good time.

Bonus: Stay till the end of the game  and you could win four tickets to the Cubs Opening Day Game at Wrigley Field, and a cute ensemble to wear to game day. Double date, anyone?

Rockit Bar & Grill

Address: 22 W. Hubbard St.

Tickets: Pre-Party Charity Event: $10 or $20 from 3:30 pm – 4:30 pm

Furever Football

If you’re more about the pre-party then the actual party, you are in luck. Rockit Bar and Grill is hosting a special Super Bowl 50 pre-party to benefit, Furever Rescue, a local animal rescue non-profit. Your ticket includes two free drinks and appetizers.

There are game-time party packages for parties, which range from $200-$400.

The Pony

Address: 1638 West Belmont

Tickets: $40 per person from 5 p.m. to 9 p.m.

There will be the usual TVs, but each table also gets their very own flat-screen. Yes, this will be up-close and personal for you. Your ticket includes a pizza and wing buffet, domestic, import and craft pints, call liquors. Specials: $4 Jameson.

Bonus: Super Bowl Half-Time competition, where you can kick a field goal to win a $250 prize. The game will be broadcast on overhead plasma TVs and at tables that feature an individual flat-screen TV for viewing.

The Super Bowl + A View:

The J. Parker

Address: 1816 N. Clark St.

I’ve always wanted to go here. It’s one of the classiest places in Chicago, and it’s not even downtown. Go up in the air for a Super Bowl tailgate atop Hotel Lincoln. Chef Paul Virant will be preparing: chili, patty melts, pork sandwiches, chili cheese fries, and sliders. Specials on Bud Light and Tecate buckets.

360 Chicago

Address: 875 N. Michigan Avenue

Tickets (at the door): $20 per person starting at 5:00 pm

Don’t eat too much or drink too much if you’re going to the 94th-floor observatory of the John Hancock Center. Like Bar Toma, this is the first time the John Hancock is hosting a Super Bowl party. They will have two 80-inch TV’s.

It’s worth noting that this is a family event.

It’s also worth noting that there is seating for about 40 people, a Hancock spokeswoman said, but a lot more standing room available, reports DNAinfo.

Bonus: Specialty cocktails themed after the Denver Broncos and Carolina Panthers are on the menu. We know you are classier than beer.

Extra Bonus: Anyone who shows up wearing an NFL jersey can ride Tilt for free!

I Need Something More Than The Super Bowl:

Howells & Hood

Address: 435 N. Michigan Avenue

Tickets:  It’s free, but $16 chili-trio packages

You’re invited to eat something besides wings on Sunday. The Third Annual Chili Cook-Off Super Bowl Sunday will add tasting and voting on something other than who is going to win the game. Zed 451 and Chop Shop will be battling for the title of “Chili Master.”

Super Bowl Parties:

If going out in groups is more your style, there are a few Super Bowl parties to join:

The Chicago Adventures Meetup Group is organizing an event Super Bowl Party @ Trophy Room: $40 3.5 Hour Food Drink Package! 56 people have signed up thus far, so you’re sure to meet someone. Start time: 5:00 pm

The Chicago Loop Happy Hour Group is meeting up at Roanoke Club for the traditional Super Bowl food and drink specials including $3.00 beers and $5.00 wine. 13 people have signed up. Start time: 4:00 pm.

Go Team:

You don’t need to cook, just show up with team spirit. Let me know how your Super Bowl boy turns into your Valentine’s Day date. I’m rooting for you because I honestly don’t know who to root for in the Super Bowl.

P.S. Windy City Cosmo’s top pick is The John Hancock. Themed cocktails, a view, a new experience, and a socially relevant game all in one? Yes, please!

P.S.S. If you are single and want to mingle, Bub City might be the better option. It’s less family and more friendly.







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.



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 on love and relationships.

Being single in Chicago is awesome. Yes, if you are single right now, I think you are awesome.

I see the Valentine’s Day decor, as well, but being single is truly awesome. And being in a relationship is only great if a) you love yourself, b) you find someone good for you.

Many of us are in relationships just to be in relationships or we date to date. Honestly, meeting new people is fun and exciting, but it can also be downright uncomfortable and exhausting.

Dating Detox:

This year, I have decided to take a detox. Yes, I know we are all trying to detox in January. But I don’t mean juicing or our average cleanse.

I mean I want a detox from men.

What does this mean? A detox from men means that I’m not going to say, “yes” to every guy who asks me out. And, I won’t ask men out on a date anymore. Nope. Not going to do it.

I have already dated A LOT in the city. And this year, I have decided to add filters and other activities to my life besides dating and cocktail parties. Okay, I’ll keep the cocktail parties.

I have been reading, I have been seeking out advice, and seriously, I have too many stories about the matter.

I hope you find your Mr. Perfect. I hope you find happiness and contentment in whatever stage you are in life. Single. Married. Divorced. Dating.

One of my favorite yoga instructors, Adriene Mishler, the founder of  Yoga with Adriene, a happy and successful online yoga community that offers free yoga classes, has the mantra, “Find what feels good.”

I think that’s the key to success and happiness. It’s not about doing certain things. It’s about doing things with set intentions and goals, and stretching yourself to be happy with where you are, but striving and working towards a better future and daily growth.

It doesn’t feel good to date a jerk.

It doesn’t feel good to have one night stands.

It doesn’t feel good to hurt someone’s feelings.

It doesn’t feel good to have unrequited love.

After reading Aziz Ansari’s best selling book, “Modern Romance” and sitting down with a few Chicago bloggers to talk candidly about Chicago food and dating, I was inspired to write a post for Elite Daily about love and standards.

Below is an excerpt from the Elite Daily article published on January, 6, 2016.

Elite Daily Article Excerpt:

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

Your life is important.

You want someone special to share your life with. But this means there are compromises to be made.

I think it’s awesome being single.

I went to a blogger dinner with nine other women in their 20s and 30s, and they dished about the single life.

Honestly, they cannot find anyone they want to factor in their vacation days and sick days for, but I personally laughed a little bit inside because I never thought that’s what it meant to factor someone else in.




There are seriously too many perks to living alone and being single.

The main one is the fact that we get to do whatever we want, whenever we want.

We can work later, we can go to events, we can buy that new dress, we can set our own budget and we can vacation where and when we want to.

Factoring someone else in and caring about someone else’s happiness is hard work.

So, yes, we have boxes that need to be checked. Yes, we would like pleasure in our love lives.

Read more of the article, “Why You Will Fall In Love With The Guy Who Won’t Check All The Boxes.”

Share Your Dating Story:

Are you recently dating someone? Share your story with me in the comments.