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.

 

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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.

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:

Katie,

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.

Love,

Sam

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.

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How We Wish Men Answered Our Bumble Messages

Saying “Hi” and “Hey” on Bumble (Tinder, OkCupid, Match, eHarmony, Hinge, etc.) is one of the worst ways to start a conversation. Just kidding we all do it. I mean sometimes swiping is like liking photos on Instagram – it could be more muscle memory than interest. Sorry, not sorry. And that shirtless, distant photo of you with the empty profile to match isn’t really telling us if you’re a bot or a boy.

Do You Want to Hook-Up?

But some of us girls have taken a different approach – a no B.S. approach if you will. Basically, we need to know if you are you a f*ck boy or if you’re looking for something more serious. I mean we all want a cuddle buddy and a dinner date every now and again but let me put it this way – is what you’re offering the $3 wine at Trader Joes or an aged Merlot from the wine shop?

We ask the questions. I know, men have said it sounds like an interrogation. But, it’s really just because you didn’t fill out your profile and I need to see more than a shirtless pic to go out with you.

So, what is it that us girls really want to hear when we message Mr. Hedge Fund on Bumble?

Everything a Girl Wants to Hear on Bumble:

What are you looking for?

A relationship (Marriage/commitment/don’t like other girl’s Instagram pics).

 

(Ok this is tricky. There’s a guy on Reddit who says he uses the line “meeting new people and seeing what happens,” but he always gets unmatched. Most guys answer the question a few different ways. I get that we both don’t know each other. So, honestly, we might just be friends or hookup or have a relationship. When I say I’m looking for a relationship – it doesn’t mean that it’s going to be with you – that’s just my intention.).

Do you Netflix and Chill?

I don’t know what Netflix is.

How tall are you?

6 ft something. (Other versions i.e. tall enough to lift you off your feet really just tells us you’re hiding something).

When was your last relationship?

2 years ago. (Anything along the lines of just got out of a relationship = rebound).

Do you think this will go anywhere?

It could if you join me for dinner at 8 on Friday night.

Conclusion:

Ever since recording my relationship podcast, Ok Cool, I’ve become obsessed with a few dating coaches/relationship experts. My absolute favorite dating coach is Matthew Hussey – let’s just say he has a monthly column in Cosmopolitan magazine and wrote the New York Times Bestseller “Get The Guy.”  He has a few tips on how to respond to men on dating apps/texting and how to get a relationship. P.S. He just got into a relationship a few days before Valentine’s Day. So, good things come to those who wait. Idk. Happy swiping.

 

 

 

 

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.

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A New England Taste for Chicago Restaurant Week at Oyster Bah

For this Chicago Restaurant Week – we took a trip – with our forks – to New England for some fresh seafood and nautical ambiance.

This week is what some people call “better than Christmas.” It’s Chicago Restaurant Week from January 26 – February 8, 2018. Chicago Restaurant Week is a dream for Chicago foodies because you get to eat a fixed price menu at some of the hottest and finest Chicago restaurants.

A few bloggers and I got together for a tasting at Oyster Bah (1962 N. Halsted) in Lincoln Park to catch up and eat some fresh seafood.

The food was good. The ambience was perfect. And the company made the experience.

Dig in at Oyster Bah:

Since I know you want to – let’s just dig in. I do really think that you bond over meals. While I love good sauces, fresh seafood, and a savory meal – time flew because of the conversations.

We did Oyster shots together and split a lobster roll. I loved how zesty and fresh everything was! Seriously, get the lobster roll and save room for the mussels!

Restaurant Week is a Great Way to Meetup with Friends and Talk About Your Projects:

Best of all, because we met up during the launch of my relationship podcast, Ok Cool, we started talking about our dating lives. Some of the Chicago bloggers shared our worst dating stories from Match and other places. P.S. I don’t really like Match – it took three months, and I only met up with one person.

My favorite story was about how a guy went to the bathroom during the dinner date and didn’t come back! My friend was left with the bill and oddly, his coat which he left behind. At the end of the night, she gave his coat to a homeless guy and had a few drinks with the bartender, who saw what happened.

Restaurant week is the best way to try favorite dishes from Oyster Bah for a set price. The lunch special is $22 and dinner is $33. Reservations can be made by here.

Battle of the 90s at Split-Rail:

Next on my restaurant week list is Split-Rail because – guys – they have a battle of the 90’s – Friends vs. Seinfeld.

https://instagram.com/p/BequJGulEN1/

All photos were shot by: The Brazen Gourmand

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.

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I Rented an Hermès Birkin Bag From This New Chicago Start-Up

A Chanel bag. A Birkin bag. That sounds like a dream closet. Just like you can live in a dream house for a week with Airbnb, you can walk around with a thousand dollar bag – or like I did –  with a $19K Birkin Bag for two weeks with the new Chicago startup, DesignerShare.

“Women love to bond over this idea of sharing their clothes and accessories with one another,” Sarah Perkins, Co-Founder of DesignerShare, the first peer-to-peer marketplace for women to rent their designer clothing and accessories in Chicago.

We’ve all envied our friends closet at one point or another – or borrowed a friend’s shirt or a sister’s earrings. But, it becomes another level when that closet includes Chanel and Hermès.

Windy City Cosmo sat down the Co-Founder of DesignerShare to learn about how some of the most coveted items in fashion are now being shared with other women in Chicago. And then, I share my experience with the service and what it was like to rent a $19K Birkin bag for a two-week vacation.

I’m ready for the weekend! Who’s with me? 👋

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The Story Behind The Chicago Start-Up:

DesignerShare started with a problem, as most startups begin. In college, Sarah Perkins had too many sorority formals to attend and not enough outfits. So, she borrowed from her friend’s wardrobes – something that resonates with a lot of women.

Rent the Runway was actually starting when Perkins was in college and she thought “I’ve done this. I just haven’t monetized it yet.”

There are other places you can rent handbags and shoes and clothes from – but all designer, and all from your peers? Nope.

Monetizing an Idea:

Having an idea is great, but finding an idea to fund it is another story. Windy City Cosmo has spoken with a bunch of female entrepreneurs. Some reach out to their network and alumni like this 3D printing jewelry start-up and some do a mix of e-mail outreach and venture capital funding, which is what DesignerShare did.

For pricing, they looked at their competitors and other sharing economy companies. They did a heavy pricing analyst.

Sarah shared the mentality, “We want everything and we want it now. We want it cheap. But people will pay for the convenience. We really focus on being fast and efficient and wanting to make sure the experience was everything she wanted.”

The start-up had an office in 1871 and used some of their resources to grow their business. They also did rounds of venture funding and used PR to gain exposure. So far, they have several articles on sites like The Chicago Tribue and DNAinfo.

They even held a  runway event at the rooftop at The Godfrey Hotel in October 2017 with other entrepreneurs like makeup and hair startup for employee perks, The Lisa App. 

Finding Balance as an Entrepreneur:

Business wise it’s always a journey. How do you grow your brand and also stay sane?

“I was raised to have a lot of balance,” Sarah Perkins shared, “I go to bed by 10 pm and I wake up at 6 am to work out. I am non-functional if I don’t get enough sleep. I take the longest naps on the weekend.”

“I haven’t gone on vacation in 8 months. I think January I’ll have a few days.”

GirlBoss Was Right: Customer Service is Important:

“We don’t want to be mean girls. We want to be the friendliest shopping,” Sarah Perkins shared.

“No one wants to leave home. I’ve delivered to a girl at happy hour,” Sarah Perkins shared. “I walk into Monks Pub in the loop. It’s a very old bar. It’s one of those places with peanuts in the bar. And I show up and say ‘here’s your clutch for her friends birthday party this weekend.’ The customer said, ‘look at this customer service, you’re delivering to me while I’m having beers!'”

And the craziest part of the story is that Sarah is allergic to peanuts. So, she literally had to find the client, deliver the designer item, and leave before having an allergic reaction.

The customer said look at this customer service, you’re delivering to me while I’m having beers!

It’s not always delivery that equates to great customer service. Sarah Perkins describes a situation where one client was unhappy with a bag and within 2-3 hours they got her a new one.

Can we get an amen?!

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The Dream Closet:

DesignerShare has expanded to 800 users and 700 pieces. Some notable items include Dyanasua bag from Gucci and two Birkin Bags.

Women Using DesignerShare:

“We really want women to look and feel great on a regular basis. We focus on the problem of people feel scrutiny in how they look, ” Sarah Perkins shared.

Clients use DesignerShare for a number of reasons  – sometimes it’s a birthday party or a vacation where women want to rent a bag or a dress.

Today, with the need to constantly go out and do photo shoots for blogging and business, it can get overwhelming (and expensive) to constantly update your closet. Chicago fashion blogger, Caitlin Patton shared in a recent blog post, “Personally, I don’t have the time or money to be spending thousands of dollars on new clothes just to take pictures in…”

It goes beyond photo shoots – sometimes it’s having a nice bag for a corporate event or an interview that can help give women a confidence boost.

Sarah also eluded to other times you want to look your best for – “like when you see your ex for the first time, you’ve got to turn it up.”

My Experience Renting a $19K Birkin Bag:

I rented a Birkin Bag – something I learned about from Gilmore Girls about and was like – who can afford a $19K Birkin bag?

Well, for two weeks, I got to be that person. And I couldn’t believe it. It’s fun to play dress up when you’re a kid – I use to make clothes out of sheets and wear clip-on earrings. But to actually play dress up from a dream closet as an adult was surreal.

I got to take it with me to visit my family in Boca Raton, Florida and then on a mini vacation to Orlando Florida for Mickey Christmas. And then I went to the Bahamas and took it with me as I had a few drinks with friends at the Bah Mar Resort. It was really nice to dress up my casual sundress and beachy vibes with a designer purse. But it also felt weird. My entire life and business worth cost less than this bag – so I tried to only take it out to classy places.

Let’s be real, a Birkin bag costs anywhere from $12,000 – $223,000, according to Fortune. I am so not used to walking around with something so valuable – it was a gift as much as it was a curse. There’s something different about renting an item from a person rather than from a company. It’s like when you spill coffee on your sister’s shirt – you know she’s going to be mad because it’s her favorite shirt. Well, I felt that liability when I rented this handbag.

The best part of my experience was customer service. I was speaking at a conference in the morning. Sarah had texted me about renting a bag. I literally got off stage and she found me a Birkin bag. On top of that, I was only home for an hour to grab my luggage and get to the airport. DesignerShare was able to work out all the logistics and deliver the bag on time so I could catch my flight.

The service was so personal and fast-paced. DesignerShare acts as a middleman between the borrower and the lender. They coordinate drop-offs by hand – without a scheduling app. They partner with Lyft to drop off and pick-up the luxury item and then they partner with Tide Spin for dry cleaning to return the item in the best shape back to the lender.

DesignerShare Empowers Women to Be Entrepreneurs:

What’s great about DesignerShare is that the women lending their items are like entrepreneurs. DesignerShare can help women take photos and they offer a suggested pricing model, which is 10 percent of the original worth of the item. But ultimately, a lender can deny or accept a request and they price their goods.

Lenders enjoy putting their closet to good use and earning money when they’re not wearing the items. We all can’t wear all our clothes at the same time.

Learn More:

To learn more about DesignerShare, you can visit their website here. 

DesignerShare had an office at 1871, an incubator in Chicago. 1871 offers events regularly and spaces for start-ups, you can learn more about their weekly events here. 

 

 

 

 

 

 

 

 

 

 

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.

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A Good Laugh About Stand Up Comedians: HBO Crashing Season Two

**There might be spoilers.

If you’re looking for a good laugh this hibernating season, I have some exciting news – HBO’s Crashing Season Two airs Sunday, January 14, 2018. The show feels so real you can’t help to feel empathy for the main character, but at the same time laugh at the average day the show takes you through.

TV should entertain or inspire or tell a story worth telling. We’re so used to it being background noise or an excuse to hookup. That’s how I felt – I couldn’t get into TV. When I went to the pre-screening of HBO in Chicago, IL with the A. V. Club, I was surprised to learn that within the first few minutes of HBO’s Crashing, I was hooked.

Crashing is a comedy produced by Judd Apatow’s Girls, and stand-up comedian, Pete Holmes about the fictional character Pete Holmes, an aspiring stand-up comedian, whose life has been upturned by his wife’s affair. It follows Pete Holmes through his day job at Cold Stone Creamery and then his stand up show at night and then him crashing at various people’s homes as he tries to get back on his feet.

HBO Tells It Like It Is:

I think what I loved about this show was what HBO does best – tell it like it is. It’s what I loved about their other show, Insecure. But, that’s another post.

To stay in or to crash on a Saturday night – that is the question. Season 2 of Crashing is tomorrow night on @hbo. I’m so nervous about comedy #tvshows because I never find them funny but I couldn’t help but laugh out loud during the Cold Stone scene. I had more fun crawling up in this bed laughing at the hilarious life of stand up comedians with chicken and waffles (and a bar behind me) than I have in awhile. We all need to rent out furniture stores for parties. 💁🏻‍♀️#willworkforchampagne #HBO #peteholmes . . . #weliketoparty #happy #chicago #chigram #instagood #blogger #havefun #explorechicago #downtown #sogood #chitown #bloggerlife #behappy #ootd #girlboss #citychic #boots #outiftgram #jumpingonthebed

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Pete Holmes is living a (below) average American life. He has a day job at Cold Stone Creamery. You can feel his pain when a dad tries to tip him a dollar and he insists – please don’t tip me a dollar. And what happens next had me practically spitting out my champagne. You’ll just have to watch.

During Season Two, Episode One of Crashing, Pete sleeps with Ali, a fellow aspiring stand up comedian. After their hookup, he lingers and thinks it means more than what it was – a one night stand. If you’ve ever wondered what it’s like to hookup with someone and then in the morning have to creatively suggest how to get them out of your bed – this cringeworthy scene is for you.

After we watched the last episode of Crashing Season One and the first episode of Crashing Season Two, we were treated to a moderated Q&A with Pete Holmes and Jamie Lee by Marah Eakin, Senior Editor, The A.V. Club.

Pete Holmes shared that this show is actually based-off his divorce from his wife. And he really did have an awkward encounter with the first person he slept with after his divorce. I found this so interesting and more excited to watch since I share dating stories on Windy City Cosmo and my new podcast, Ok Cool, based off my life.

Preview of Crashing Season Two: 

Crashing Image

With the help of Ali, a fellow rising comic, Pete explores the alternative comedy scene, a world of comedy nerds, apartment shows and no-drink minimums, where he begins to thrive. As he continues to lean on the hospitality of comedy greats, Pete explores all types of comedy, from benefit  shows to the college market to roast battles. These diverse encounters test his enthusiasm and optimism, but also promise to make him a better comedian as he tries to survive the competitive world of New York stand-up.

Pre-Screening Party:

To celebrate the second season, Windy City Cosmo joined The A.V. Club and HBO for a party at a rented out furniture store because the only way to watch a tv show is on comfortable beds and couches.

It was definitely a new way of networking to sit in bed and be like, “can I join you?” while we talked about serious matters like freelance writers affected by Facebook and Instagram’s changing algorithms which have shut down publications. The juxtaposition made the night awkward and funny like the show.

Besides good people, there was also good food. I picked the bed with the bar behind it so I had champagne basically poured to me from bed. I feel like everyone should put a bar in their bedroom, but that might be dangerous.

We also had a full breakfast bar – amazing chicken and waffles, an extensive chocolate and glazed donut wall, and milk in various cereal flavors. The milk was definitely weird – it tasted as if I just had a bowl of fruit loops without the fruit loops.

If you’re going to watch Crashing, I suggest doing breakfast for dinner. It airs on Sunday, which is a nice day to relax and maybe make some mimosas and eggs while experiencing the life of a stand up comedian, Pete Holmes.

Cheers and happy hibernating!

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.

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