I Planned A Drake Themed Galentine’s Dinner Party In 5 Days And It Was Everything

Having dinner with girlfriends is the best. But add cake and Drake songs – it’s simply the perfect theme I could think of for hosting my first Galentine’s Day dinner in Chicago.

I love a good party (see here, here, and basically all of my Instagram stories). And the reasons why I love them is because they help you bond with people. This Galentine’s Day dinner party was no exception.

First, I’m going to walk you through how I planned the Drake Themed party in five days- from the Drake on a Cake to the location.

Then, I’ll share with you what we did at the party.

How We Got to Drake on a Cake Galentine’s Theme:

The theme was Drake on a Cake. How did we get here? It all started with Chicago Restaurant Week and God’s Plan.

I was having a late lunch, which turned into early cocktails with a few fab Chicago lifestyle and food bloggers.  Drake had just released the song, God’s Plan, and we started talking about the lyrics which led our Instagram-obsessed selves to Drake on the Cake Instagram account.


Nicole Triebe from Windy City Dinner Fairy at Restaurant Week. Photo by: The Brazen Gourmand


During the lunch, I met the infamous Nicole Triebe, Founder of  Windy City Dinner Fairy, who I had followed on Instagram, but we’d never met in person. And, I’m going to tell you, meeting in person is so important. 

The day we met for Chicago Restaurant Week was also the day I started to promote my new relationship podcast, Ok Cool. We started talking about dating stories in Chicago and we were swapping our worst date stories.

Drake + Good Lobster Rolls + Bad Dates = BFFS


After a few laughs, some mussels, and some good cider, I had to interview Nicole about Windy City Dinner Fairy for my blog. So, we set up a date to make a Drake on a Cake and learn more about how she started baking and cooking.

The Drake on a Cake: Making the Cake:

About a week later, what was just girl talk, turned into baking the Drake on a Cake. I started my afternoon with Nicole from Windy City Dinner Fairy with a bottle of champagne. She already had the eggs and some ingredients on the table. Without a recipe, she swirled the batter and tossed in the ingredients to make a double chocolate Drake on a Cake.


Baking a Cake with Windy City Dinner Fairy.


Meet The Girlboss Behind Windy City Dinner Fairy:

While her cake smelled sweet, her story of becoming a girl boss was about a 15-year long road. See, Nicole always knew what she was good at, but it took time to develop her skills and her clientele. She was working a full-time job as a Paralegal when she started her creative, custom dessert catering company, Windy City Dinner Fairy. She was catering with a friend and made pastries for a coffee shop. And then on her own, Nicole was hired as a personal chef for three CrossFitters. It was when she made cupcakes for a wedding that she realized that this was what she wanted to do. She switched jobs to be an Assistant Underwriter at an insurance company and still kept making cakes and food on the side. Her business had expanded throughout the Chicagoland area. After working two jobs, which she didn’t like very much, she was ready to incorporate her side hustle on her 35th birthday – December 1, 2017.


The cakes were cooling, and it was time to pop the champagne. After hearing her story, we brainstormed the best Drake lyrics. Ultimately, we went with “You The F*ckin Best.” Windy City Dinner Fairy then made then made a “You The F*ckin Best”  playlist as she finished icing the cake, and I finished the champagne. I knew that those weren’t just empty words on a cake – she really is the f*ckin best for quitting her job and making her side hustle her business.


We Chose the Drake lyrics “You The F*ckin Best” for The Galentine’s Day Cake. 


P.S. if you need a visual of what it was like to bake with Nicole, you can watch her in action with Glossed and Found, an online video magazine making a hydrangea cupcake bouquet for Valentine’s Day.

The Galentine’s Day Invites:

One Party Can Lead To Another if you just believe. Chicago influencers from Chicagogrammers came to the Drake on a Cake Galentine’s Day Party. 

I think the only thing to do with a cake is to have a party. So, I went to the monthly Chicagogrammer’s happy hour with 30 other Instagrammers on Wednesday, February 7, 2018.

Some of them had seen my Instagram stories and asked me what Drake on a Cake was.  After Chicago bloggers and influencers Alyssa Erickson from Doughscuit, Allie Barke from Alliesfashionalley, and Katie Cahnmann from Appetite_4_Adventure were interested – I decided it was for a party.

A handful of people were going to the Chicago Pizza Party like Allie Bahcall from Bahcallmemaybe, who works for Yelp and the other half had no plans –  so we choose Saturday night.

I literally met new people that night like Ratanya Bowens and said, “Hi, I’m Amanda, what are you doing Saturday night?” With the blizzard coming on Friday, I knew the more invites the merrier.

So, I had a cake. I had people. Now, I just needed a time and a place. Three days till the party.

The Place to Host a Dinner Party:

Dinner parties are my favorite thing. I realized that I’m still an aspiring cook and so I appreciate the many wonderful chefs in Chicago who introduce me to new foods and flavors.



We had the Galentine’s Party at Urbanbelly in Wicker Park. We had a big table to the side with a green wall in the backdrop for the semi-private dinner party.


I went out the next day to a handful of restaurants in Wicker Park and talked to the managers about hosting the dinner party. All three of them were great spots – Bru Chicago, Piece Brewery and Pizza, and Urbanbelly. 


I knew I wanted a semi-private event space where I could set up some type of decor. I ultimately chose Urbanbelly because they had this beautiful green backdrop and a nice table space with a corner area for us to drop our coats and purses and do what girls do best – relax and talk. Plus, the manager, Elizabeth was so nice.

The Decor:

If ever there was a time for a Target Run – it’s for a party. Target has really cute decor for $1 or $3. I picked up some cards, balloons, some pens and stickers, and a few photobooth props.


Appetite 4 Adventure and AlliesFashionAlley were some of the Chicago bloggers at the Drake dinner party. 


Plus I got some champagne gum as a palate gum. It made a great conversation piece.

The Night of The Drake on a Cake Dinner Party:

Let me just say, I loved everything about this party. Urbanbelly in Wicker Park had the table reserved for us with water and chopsticks already on the table.

We all decided on which Ramen and dumplings to order – don’t forget the dumplings. They are small, but flavorful. I got the beef and cheddar and the chicken curry. They were so good! And then I ordered togarashi fries for the table. Which were perfect in between good, spicy bites of my chicken ramen.

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Last night was messy, funny, and as real as a Drake song makes me feel. My dreams came true – I threw a Drake themed dinner party for Galentines Day. We made Valentine’s Day cards from Drake lyrics and had a Drake on a Cake. I went to a few restaurants to host the party and @urbanbellychicago was wonderful and made us feel special. After ramen, some dumplings and piña coladas, the manager brought us amazing ice cream shots and pb&j ice cream – soft serve with crunchy peanut butter and huckleberry jelly that even @seriouseats recognized as some of the best ice cream in Chicago. The food was amazing! And I had never been there before. Getting a card written from Drake lyrics made us all laugh and most of all I had amazing company. Cheers to week of love and laughter 🥂

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I had never been to Urbanbelly before – but everything was good and everyone loved it. I learned that the master chef is renowned Chicago chef, Bill Kim, who has been awarded a Michelin Bib Gourmand and the StarChefs Rising Stars Award.

One of the best parts of Urbanbelly is their cocktails and desserts. Seriously these can be extras and often overlooked when having a big bowl of ramen. But, we had to try. They have house-made signature cocktails including a new pina colada inspired cocktail. I went for the cider.

Making Valentine’s Day Cards From Drake Lyrics:

After we shared dating stories and caught up on life. I had everyone put their name in Valentine’s Day bag. We all wrote out Valentine’s Day cards to each other using Drake lyrics. I think this was one of my favorite parts of the night!


We pulled names from the Valentine’s Day bag to write personalized notes using Drake lyrics. 


The best Valentine’s Day card made via Drake Lyrics was:


Tonight was your night. Go get you some lobsters and shrimp.

You smart and you know it. I get it. I get it. You outdo those pimps.

Happy Valentine’s Day.



I mean Drake lyrics written as a card had us all laughing.

The next part was dessert. The manager surprised us and brought us some of Urbanbelly’s dessert to try and it was seriously amazing. If you only have room for one dessert – order the shake shot. I was confused when they put a mason jar filled with soft serve and shot glasses on the table – but taking a shot of ice cream is now one of my favorite shots. UrbanBelly’s shake shot has vanilla soft serve, Vietnamese iced coffee & chocolate crisp on top.


After Ramen, we took cake shots – which are just as amazing as they sound. 


I’ve never tasted peanut butter and jelly in ice cream form – but it was better than the sandwich. They take crunchy peanut butter and mix it with berry compote into the vanilla soft serve. Then, we also sampled the soy caramel soft serve.

Finally, it was time for the cake behind the party – Drake on a Cake. Urbanbelly cut the double chocolate cake and served us. The homemade frosting was so good!

Happy Galentine’s Day:

Our bellies were full and my heart was filled with joy. I’ve always wanted to throw something ridiculous like a Different rake on a Cake party. Celebrities have been my muse for several parties. For my 25th birthday, I threw a 1989 Taylor Swift party and we shut down the bar to make a music video to Shake it Off.


We finally got to eat the Drake on a Cake. 


So, that’s how you throw a party in five days. Hope you have a great Galentine’s Day and thank you for reading Windy City Cosmo! Remember, you’re the f*ckin best.

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.


Fourth Annual Zombie Pub Crawl in Wicker Park

Outside looked like the end of the world, and for some it was at the Fourth Annual Zombies Vs. Vampires Crawl on Saturday, October 24, 2015 in Wicker Park.

The pub crawl started at 2:00 pm, which was early. It was really early, especially for those who were still feeling the effects from last night.

Chicago Pub Crawl Zombies on Milwaukee Ave. Photo: Amanda Elliott

Chicago Pub Crawl Zombies on Milwaukee Ave. Photo: Amanda Elliott

People came between 12:00 pm and 2:00 pm to check-in at Halloween Hallway (1355 N. Milwaukee Ave.). Groups of zombies and vampires took over the telephone booth and Milwaukee Avenue while taking group photos and selfies. But, inside the bars, there was a light flow.

The various stops on the pub crawl helped to spread out the crowd and make for a tame afternoon, and a more festive evening. Bars started to crowd around 5:00 pm. The crawl ended at 8:00 pm with an after party at Emporium at 8:30 pm.

The Bars:

  • Nick’s (1516 N Milwaukee Ave.)
  • Flat Iron (1565 N. Milwaukee Ave.)
  • Tavern (1958 North Ave.)
  • Standard (1332 N. Milwaukee Ave.)
  • Emporium (1366 N. Milwaukee Ave.)
  • Swig (1469 N. Milwaukee Ave.)
  • Pint (1547 N. Milwaukee Ave.)

There were special zombie cocktails and vampire cocktails as well as Fireball shot specials.

Zombie Make-up Artist:

The crawl began at Halloween Hallway. People were already dressed as zombies with full make-up. But, for those who didn’t know how to do costume make-up, there was an on-site artist who would paint your face for free.

She was one of the coolest aspects of the pub crawl. After seeing my face when zombies walked by, she transformed me into a tame zombie.

Best Dressed Zombies:

There were a lot of creative costumes for the crawl. Even midday, people came in torn jeans, stitched jackets, and smoky faces. One participant dressed as a zombie lifeguard. She is a swim teacher and used that as inspiration for her outfit. For her prop, she used a blue blanket and affixed it with white athletic tape. To maintain the shape, she placed a wire hanger under the blanket.

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Frank & Oak Open Second National Men’s Fashion Store in Wicker Park

There’s a wooden crate in the corner, which I have deemed my bar ledge for the evening. It was made hours ago by the project coordinator, who transformed the previous pallet.

“A great use of upcycling,” the store manager smiled as he waited for me to try my first drink.

Under the wooden bar, there was an entire keg of Kallisty, a pale ale from the Chicago brewery, Illuminated. Two men, one in grey and the other in plaid, managed the bar as they poured the frothy beverage for twenty Instagramers and journalists at Frank & Oak’s media pop-up event on Wednesday, August 5, 2015.

The second of Canadian men’s fashion company, Frank & Oak’s retail store is about to open. It sits on the corner of Wabansia and Damen, a few blocks from the bustle of restaurants and nightlife underway on a weeknight in Wicker Park.

I walk in and it’s simplistic.

“You don’t see 20 TV’s, but you see technology,” Eric Alper, the new SVP of Marketing said.

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Frank & Oak Members Choose American Cities for Store Opening

Three years old, Frank & Oak started exclusively online for members only. Last year, the company began opening retail stores in Canada. This year, Frank & Oak made the move to expand to America in a unique way.

A company built on community, Frank & Oak turned to its 2 million members for inspiration. Through gift card purchases, the 2 million members chose which cities would get their very own Frank & Oak retail store.

The first was Boston, which opened in June 2015. The second store is opening in Chicago this August with an event on Saturday, August 8, 2015. More stores will roll out throughout the year in various cities, which are to be announced.

Chicago Men’s Fashion Store Grand Opening

Frank & Oak’s grand opening begins in the morning on Saturday, August 8, 2015. While shopping to beats from DJ MattBoyWhite and eats from BBQ by Lillie’s Q, the first 40 people to arrive can pick up a shirt or accessory for free with a $50 gift card to Frank & Oak.

The grand opening event will start at 10:00 am with a BBQ from 11:30 am to 3:00 pm and the DJ from 4:00 pm to 7:00 pm, when the store closes.

3 Ways to Upgrade Your Style

I sat down with Alper, Frank & Oak’s SVP of Marketing to talk about how men can elevate their style.

Alper offered three ways for men to transform their look.

  • Nail the Basics. Get a pair of black shoes and brown shoes. Have several washes of denim to mix or match.
  • Start layering. Layer down for summer and layer up for fall and winter. An example of layering down would be a t-shirt paired with a short-sleeved button-up top.
  • Be bold with one piece. Alper showed me his purple polka-dotted dress socks. Being bold can also be achieved by incorporating a detailed jacket or adding a pocket square to a suit.

The Men Who Wear Frank & Oak

Frank & Oak targets men in their mid twenties to mid thirties, who are just starting out in a creative field. These men are in transition. They may be upgrading their look from t-shirts and jeans and need a personal stylist and a simplistic brand to elevate their debut or climb in the creative field.

Frank & Oak’s Style

Frank & Oak offers basic shirts and button-up shirts.

“The fit is more slender on the shoulder than the athletic cut,” Tommy Nouansacksy, one of Frank & Oak’s style advisers noted.

The Chicago store features three jackets, one being the suit jacket. Their clothes are lightweight and convenient. They are available in subtle tones like black, grey, and burgundy. While the average attendee was medium build, Frank & Oak is available in regular sizes and tall. To complete the look, they offer classic shoes and sleek travel bags, as well as accessories from your pocket square to your cuff link.

The Chicago store will have personal stylists available to help you find the right fit and look. Every month, look for a new collection from Frank & Oak’s team of 13 in-house designers.

Frank & Oak Store Opening Photo: Frank & Oak

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.