Chicago – A Real Look At A Long-Time Love Affair

It’s Our FINAL Week In Chicago.

That’s right. After over 2 1/2 years running at the Up Comedy Club in Chicago, #DateMe is entering our Final Weekend!

Here’s me in February 2015 thinking we were only going to run for Three Weeks.


Cut to over 2 1/2 years later and this is how I feel…


Ironically, this has been one of the longest relationships of my life.


And What A Love Affair It’s Been!

Mostly full of the Highest Highs. Thank you:

  • Amazing audience
  • Positive Casts (past and present)
  • Positive Crew (past and present)
  • The supportive people at Second City (Hollywood & Chicago)
  • Our producer Diane Alexander! (The BIGGEST Thank You!)
  • OkCupid – a site that I genuinely Love (with all due respect, Tinder, there’s more to people’s personalties than just Swiping Left & Right!)
  • The staff at 1959 Kitchen & Bar for always making us feel welcome and loved.
  • The house and wait staff who said “Hello” back. Small things. But it means a lot.
  • The cast & crew of our original show, Undateable. ALL of you are AMAZING.
  • Windy City Bloggers and reviewers who showed so much love.
  • And many, many more.

So. Many. Highs.

And with those highs sometimes come the lows — some that made me question everything about myself and my career. I know.


But it’s for reals!

Not whining. Just explaining. Trust me. I’m building to something here…

Along with the ongoing pressures of:

  • Being a woman in comedy
  • Constantly trying to prove myself as a writer, performer, and creator of the show (I never felt I was good enough!)
  • Trying to stay sane while being away from my family, friends, my boyfriend, & LA community
  • Being terrified I wouldn’t be able to “bring it” the night a life-changing VIP or critic was in the audience
  • Worrying our constantly AMAZING audience would be stone-faced & quiet the night a life-changing VIP or critic was in the audience
  • Worrying. In general.

Along with ALL that, there were also just some not so nice people along the way.

Haters, You Know Who You Are!


And it’s okay. I forgive you.

(Why in the world would haters care if I forgive them if they HATE me?! Good Lord, Robyn.)

Now this is not a blog to rant. I want to be Extremely Clear that there have been so many WONDERFUL people along the way. And being at Up Comedy Club in Chicago has been a beautiful dream!

You CAN Go Home Again. It Will Just Be…Different.


I’m just reflecting about leaving Chicago, a place I once called home and loved SO much. And a place that, coming back to, felt… different.

So I guess I’m writing this to move on. To celebrate the good. And put to rest the hard times.

Robyn, this is the first we’re hearing about this. What are you talking about?!?!

Oh, yes. Sorry if this is coming out of left field.

99% of my experience with this show has been positive! And that’s what I usually focus on here. The performances, people I work with, and audience members are the BEST. That’s not what I’m talking about.

There has just been some hard stuff within the community that I once felt such a huge part of.

To be blunt…

I Do Not Remember It Being So Negative When I Was Coming Up.

I always feel like…

“Aren’t we all in this together?”

I’d be (and AM) so happy for any of my peers that succeed. There IS room for all of us.

I guess because things don’t come easily for me, I don’t get jealous or upset when I see others succeed. It gives me great joy. And also inspires me to keep going.

But I DO understand that sometimes this comes with the territory.

And, as my good friend Tim Whetham used to say to me…

“There’s no room for hate in your little heart.”

And there isn’t. I’ve learned SO much. I HAVE made mistakes. And I have become a stronger person because of it.

I Understand (I Think).

I never see things in black and white and I’ve tried very hard the past three years to put myself in the shoes of anyone I didn’t understand.

  • Maybe it was fear.

What is this new show that came from LA and took over our space?


  • Maybe it was jealousy (although I feel that’s a bit of a go-to excuse. And also a bit conceited to assume people would be jealous of you.)
  • Maybe people thought we were given special treatment?


But the reality is that everyone working on this show behind the scenes works INSANELY hard. Every day.

And we had to really push to get all of the extra things that we have:

  • lobby experience
  • social media
  • the multimedia aspects

It was all very hard to explain. And even harder to implement.

  • Maybe it was just not knowing who I was.


Who is this random girl that just dropped into Chicago, via LA, and took over the Up Comedy Club?

Anyone who knows me knows how hard I work. And that things don’t come easy for me.

BUT I can understand that if you DIDN’T know that you might be a bit resentful wondering who I am and why I’m at Second City — a place that so many people strive to work at.

The History

The truth is, I’ve worked for Second City since 2005.

And it wasn’t easy for me to get hired. I auditioned 7 times. And I had to write and produce five full length shows on my own before even becoming an understudy for Touring Company.

This business is tough. And very few people just luck into anything.

So if you’re feeling like everything else is coming easier to EVERYONE else, know that you are not alone.  Filter out that outside noise. Focus on yourself. Follow your own path.

Keeping It Real.

I usually try to keep it 100% positive on social media and here at DateMe Diaries. I’m not naive or a Pollyanna. There’s just enough negativity out there in the world and I don’t want to add to it.

As much as there are days where I want to write a tell-all of everything that has happened…

(or that I’ve heard said about me – Yikes, I sound TERRIBLE!)…

…it’s just not my style. This is the most you’re ever going to get out of me publicly. No specifics. No names. Sorry, America!

But Seriously…

Artists – Can’t We Support Each Other?

There are so many things bigger than us happening in the world right now. This is not just about me. I hear so much gossip. And I see so many attacks on social media.

We are here to bring joy and laughter into the world. Let’s not turn on each other.

I write all of this not to feel sorry for myself. Because I don’t. At all. I know how lucky I am.

I write in the hopes that any other performers or people chasing their dreams who might be having a hard time, for any reason, can know…

It Is Totally Normal To Doubt Yourself.


I know I come off as positive and confident onstage. And that IS one part of me.

But it’s not easy to put yourself out there every single day. It requires an immense amount of physical and emotional work, often to be told (or feel) at the end of the day that you’re not good enough.

Since this show began I’ve tried:

  • yoga
  • running
  • long walks by the lake (10 miles last week!)
  • meditation
  • journaling
  • healthy eating
  • reality TV (escape)
  • rose – (bubbly & pink should equal happy!)
  • chocolate
  • unhealthy eating

ANYTHING to clear my head. But sometimes I just can’t shake my nerves or scary thoughts.


I think (I hope) this is normal. And that most artists go through this at some point.

I’d like to think my hard work over so many years is finally paying off and it’s now easy street. But the truth is, it’s still a lot of work. And will continue to be.

But It IS Worth It.

If you stick with it, the rewards can be Incredible.

I am hopeful for a very bright future working with kind and collaborative people. And I wish the same for you.

So, please…


Okay? Okay.

Not Everyone Wants You To Succeed. Keep Going.

There’s a line in the show early on where I say I’m…

“…in a career that tests my self-esteem Every Day.”

And that couldn’t be more true.

I then go on to say, slightly self-loathingly…

“My life is AWESOME!”

But let’s be real. THAT is the greater truth.

What a Ridiculous GIFT it has been to perform variations of #DateMe every week for almost Five Years.

AND at Second City — A place I read about as a high school comedy nerd in Indiana, but never dreamed I could be a part of.

It has been surreal, to say the least.

All Good Love Affairs Have Highs And Lows.

My goal was to Start #DateMe in Chicago. Not end in Chicago. And that is still the goal.

Our Chicago stay lasted much longer than I thought.

And I am eternally grateful.

Thank You. Thank you. Thank you.

And now onto those people that Give Me Life every single weekend…

YOU — Our Audience!

Every week we feature our favorite moments from the previous week’s #DateMe audience.

We had submissions via:


Follow us on those platforms!

Who knows. YOU might be featured!

Audience Member Of The Week

Let’s just dive right in.

This past week an audience member named Chris started a trend that is my new Favorite Thing — sharing quotes from the show on social media.

It Started With An Early Pic Of The Stage.

Screenshot 2017-08-11 14.13.08

And Then The Show Quotes Poured In…

Screenshot 2017-08-11 14.13.21Screenshot 2017-08-11 14.13.17

I LOVE that Chris shared these because they are REAL quotes from users I encountered on OkCupid.

And Finally, A Definition From The Show…

Screenshot 2017-08-11 14.20.24

Chris, you are the best! Thank you for sharing with us.

Speaking of sharing. Let’s move on to…

6 Things You Can’t Live Without

One of the questions OkCupid asks their users is:

“What Are The 6 Things You Can’t Live Without?”

We recite several of these answers from user profiles Verbatim in #DateMe.

But then we want to hear from YOU.

We asked. You Tweeted.

Here Are This Week’s Favorites:

Screenshot 2017-08-11 14.13.40

Haha. (Turns Out) People Like Their Organs…

Screenshot 2017-08-11 14.13.49

After THAT Number 5, It’s Tough To Come Up With The 6th.

People Love Their Partners:

Screenshot 2017-07-31 18.17.25

Aww… So Sweet, Kelly.

Patrick Gets A Bit More Specific:

Screenshot 2017-07-31 18.16.52

Patrick! We Hope You Love Her AFTER The Baby, Too!

And Even More Specific:

Screenshot 2017-08-11 14.11.35

SassyCat, We Appreciate The Blunt Assessment Of Your Hubby’s Qualities.

Screenshot 2017-07-24 14.04.18

Salmon…Sounds Like A Party!

Screenshot 2017-07-24 14.08.02

Hatred Of Geese?! Haha. And Coke Over Pepsi? Emilee, I Am In Love.

Screenshot 2017-07-31 18.16.18 2

Benjamin, Let’s Be Real – You Just Wanted To Say “Detroit Sucks”.

Screenshot 2017-07-31 18.16.41

Thank You For Practicing Safe Sex, Matthew!

Screenshot 2017-08-11 14.13.45

Profile Names

We ask our audience to create their own Profile Names.

This Week’s Favorite’s Are:

LoLo & Fuzz – Way Too Cute!

LoLo & Fuzz

From Cute To Fierce! Meet Satan & G-Spot.

Screenshot 2017-08-11 14.30.02
Satan & G-Spot! Perfect matches according to #OkCupid

They were kind enough to share a full Instagram story.

Hey, even Satan can find a G-spot love.


Favorite Pics

I’ll do my regular collage of pics below. But some audience Pics need to be posted with their captions…

Fitting Name — “The Real Muscle Dork”.

Screenshot 2017-07-26 11.21.41
“It felt right in the moment” — TheRealMuscleDork

Just LOVE This Pic. And The Kind Words!

Screenshot 2017-07-26 11.24.59
Rimanelli Is Feeling Herself!
Screenshot 2017-07-31 18.38.25
Plot twist – we still can’t stand each other. #hesnotmyboyfriendeither #stopwondering
Screenshot 2017-08-11 14.18.05
When you and your friends have different values. – Kitties! Kitties! Kitties!… NO,

Sometimes Our Audience Volunteers Connect Post Show!

Screenshot 2017-07-26 11.29.22
Great getting to meet this girl. What an awesome night!

AWW! I LOVE them! And speaking of Love…

We Gotta Celebrate The LOVE!

Screenshot 2017-07-26 11.17.01Screenshot 2017-08-11 14.11.22Screenshot 2017-07-31 18.18.12

#DateMe Photo Booth

As always, I’ll close out this post with some of my favorite photos from the #DateMe Photo Booth & show this week.

There were TOO many good ones to choose from! If you want a bigger view, just click the photo.


This Is Our FINAL Weekend In Chicago!

We hope to see you at UP Comedy Club for #DateMe: An OkCupid Experiment THIS WEEKEND!

Stay tuned next week for a #DateMe retrospective. And a LOT of Thank Yous!

AND don’t forget to follow DateMe Diaries on ALL the platforms for daily content:

Stay tuned to find out where the show lands next. Exciting stuff is in the works! XO

Much Love,


Posted by

I'm Robyn Lynne Norris, the creator of the live comedy show #DateMe: An OkCupid Experiment. I'm overly emotional & I believe in love. If you're reading this site, I probably love you. Maybe not in THAT way. Love can mean many things. Don't make this weird. Xoxo

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