Q&A with Robyn Lynne Norris, the writer and creator of the popular #DateMe: An OKCupid Experiment on what it took to get on stage at Second City, fooling people as a crazy cat lady, and her advice for those looking for love through the internet

By Trent Modglin

#DateMe: An OKCupid Experiment returns for a fifth extension at Second City’s UP Comedy Club, 230 W. North Ave., from Feb. 4-May 29, 2016. Click HERE for show schedule and ticket information.

Click HERE for our original review of #DateMe: An OKCupid Experiment.

Q: What is it like being associated with Second City, let alone performing your show there?

A: Performing with Second City was always a dream of mine. I moved straight from college to Chicago and dove into classes and the entire improv and sketch community. I studied everywhere I could, wrote several shows and eventually was hired into one of their touring companies. I’ve traveled the world and had many of the best experiences in my life because of Second City, including writing and performing on the Vegas strip. So I’ve always held them close to my heart.

When I moved to Los Angeles, I thought my time of touring and performing in bigger venues on the stage was over. I was pursuing on-camera work and happily teaching in the Second City training center in Hollywood. But I missed the stage. So my friend Bob Ladewig and I got together to write a little show called Undateable.

We applied for a three-week run at Second City Hollywood, but Josh Funk (the artistic director) saw potential in the show and gave us a three-month run on Friday nights. We were thrilled! And thought we’d have a nice, long three-month run and then move on to the next project. But something about the show resonated with audiences, and it is still running in Los Angeles two and a half years later. It’s currently the longest-running scripted show in Second City Hollywood’s history. Insane!

Second City Chicago saw the show, and we worked on building it into a full two-act play with a narrative arc, which is something a little bit different from traditional Second City shows. I wasn’t sure audiences would be ready for that kind of ride at Second City, as there is an emotional core to the show that people might not expect. But thanks to a very supportive producer (Diane Alexander), I really wanted to try.

We opened #DateMe in Chicago in February for a three-week run. I remember one point during rehearsal when we were singing the song towards the end of the show. The lyrics and music were beautiful, and I was onstage with the cast around me… it just felt surreal.

At that moment I flashed back to the time I was 22 and had just moved to Chicago after a huge snowstorm. And I would walk 45 minutes every Tuesday night from my temp job through the snow to get to my Second City Conservatory class. Because I knew that’s what I wanted to do. But I never pictured myself as really being able to do it. I mean, subconsciously I must have, but in the real world, I always assume there are so many other people who are better for the job. I never pictured myself here with a show quite like this. I am able to perform comedy, but also utilize my dramatic theatre background as well.

We are about to begin our fourth extension of the show in October. The little three-week run in February is still going. And I couldn’t be more grateful. And still in major disbelief.

Q: For those who haven’t seen the show, can you describe what was
behind your “scientific experiment about the online search for love?”

A: Absolutely. This show began more as an experiment than just a comedy show. It is based on real-life events that happened to me right after I moved to Los Angeles. A good friend of mine, Lauri Roggenkamp, called me one day to ask if I was on the dating website OkCupid. I was not because I am a stubborn, old-fashioned romantic. She had just created a profile and wanted me to log on to check it out and see if she wrote anything “weird.” Well, it turns out you have to have a profile in order to look at other people’s profiles.

So instead of sucking up my pride and creating my own profile, I took five minutes and created a crazy cat lady that I thought was hilarious named TracyLovesCats. She was very one note and only talked about how she loved KITTIES!! And CHOCOLATE! KITTIES! KITTIES! KITTIES! I looked at Lauri’s profile, gave advice, and then forgot about it. But three days later some girlfriends and I logged on and discovered hundreds of messages to TracyLovesCats. Men had really taken the time to talk in cat speak. Lots of “meows”… fully thought-out paragraphs of meows. It was hilarious.

Then it occurred to me that I was still single, and this crazy cat lady was more popular online than I was in real life. Was it really that easy to find connection with people online? And I posed the question: Is anyone truly undateable online?

My friend Bob Ladewig and I got together and pulled in four of our friends for a photo shoot. And we created 38 undateable characters and posted them in the top 10 cities for online dating in the U.S. We set up parameters for how the experiment would be conducted so we wouldn’t lead people on or hurt their feelings.

1. We can’t start conversations with other people. “Regular” people have to initiate conversations with our crazy characters.
2. We have to use our own pictures or pictures of our friends who are in on what we’re doing.
3. We have to stay in character and push the boundaries of being undateable.
4. We can’t lead people on. Believe it or not, there are a lot of lonely people on the internet, and we can’t mess with them or their hearts.
5. We are never going to meet anyone in person.

Then we tracked the results for months with excruciating detail. And developed the show in which we take the dialogue from the real people we met online mixed with our original character dialogue to present our findings of the “experiment.”

It was a very unique process for writing a show in that we don’t change the real people’s dialogue in order to punch it up or make it funny. We wanted to represent the reality of the people you meet in the online world and treat the material with integrity. But that also means we can’t write scenes or embellish on “what ifs.” So we had to find interesting ways to present the material so it would translate to the stage.

Q: I know it’s all fun and games, but at any point did you feel bad
about fooling people with all your crazy fake profiles?

A: I felt incredibly bad at times. I tend to feel bad about everything on a daily basis. Even when I don’t do anything wrong. I’m just a very sensitive and empathetic person.

So even though Bob and I set up those rules and parameters to protect people, I felt guilty. We never reached out to people to try to hook them in or lead them to believe we wanted a relationship with them. But people did respond a lot to our characters. Overall, the response was incredibly positive. People loved the characters. And even if they had a hunch it was fake, they still wanted to play along.

But there were several people that touched my heart. If I thought they believed the characters were real and they were looking for genuine connection, I would always write them back. I was careful to let them down easy so they never thought we were leading them on. But it still made me feel bad.

I’ll see someone in a supermarket with ice cream, and I’ll invent an entire backstory about their life and how lonely they are — how they obviously just went through a terrible breakup and they’re buying that Ben and Jerry’s to console themselves. When in reality, they might be perfectly happy and just enjoying some ice cream!

So imagine where my mind went during this experiment. I cried. A lot. I started to feel enormous pressure to respond to every single person because I didn’t want anyone to feel bad or rejected. At a certain point I became obsessed with connecting with people and making them feel good, and Bob had to step in and intervene saying, “Everyone gets rejected online, and most people don’t respond to messages. It’s not your job to save everyone.”

So, yes, I felt bad. But the overall response was incredibly positive online. We never had anyone reach out to us and accuse us of being mean spirited or leading them on. And we worked really hard to represent everyone on the stage with respect and humanity.

Q: In our review of the show, we enjoyed the idea that, despite some weird interactions, you seemed to appreciate people’s desire for human connection and how it feels good to know you’re not alone out there. At what point did this message hit you?

A: I’m so glad you picked up on that. This message hit me a couple months into the experiment. When I was really obsessed with responding back to everyone. The experiment started as just a silly, funny thing. We would laugh at the ridiculous (and often times lewd) responses we got. And we knew it would be funny and interesting.

But as it went on, I saw that people really were enjoying the characters. And we were having real conversations and connecting. It was over the holidays in Los Angeles, when everyone goes out of town and the city shuts down for weeks. I had no holiday plans and was feeling pretty lonely, in general. So having this distraction provided me with something to take my mind off of some serious things that were happening in my life at that time.

I responded to all the messages that were earnest inquiries. And sometimes I really did feel myself connecting to people. Even though I wasn’t looking to date at the time, I would read the profile pages of every person that messaged us and wonder what their lives were like.

OkCupid is unique in that it gives users the ability to write their own mini biography about themselves. I was fascinated by how people choose to edit themselves. Or not edit themselves. And after a while, the lonely messages, the hilarious messages, the lewd/offensive messages and the sweet messages all started to seem really beautiful.

There’s something really brave about putting yourself out there for the world and telling people who you are and what you’re looking for. And that really resonated with me and forced me to look at myself and my real-world life a little differently as well.

Q: Having seen so much craziness while gathering material, do you have any advice for those getting involved in online dating for the first time?

A: You know, I was really a bit judgmental of online dating when this whole thing started. I always felt I’d meet my soul mate in some magical, fairy tale way. But after doing the experiment, I have to say I became way more open to online dating because there are some really terrific people out there just looking to find their person. So don’t be judgmental about it. Dive in.

It’s no different than the real world, really. There are still the same number of creepers out there. But there are also nice, kind, funny and wonderful people. You just have to trust your gut on who you connect with.

But you also have to be honest. If you try to present the best/watered-down version of yourself or a photograph that doesn’t look like you, it’s probably not going to work out. You will get initial hits, but then face more rejection down the line.

I’d say put your best foot forward, but also express yourself. If there’s something a little geeky or weird that you’re passionate about, put that in your profile. That’s the beauty of online dating. You can find people who share your passions a little faster than you can in the real world.

Also, be patient. Guys face a lot of rejection, so ladies don’t be mean to them in your responses. And guys, please understand that attractive women’s inboxes are flooded. For every message a man receives, a woman gets 17. So if the ladies don’t get back to you, try not to take it too personally.

Q: After all your success with this show, what’s next for you in the
comedy world?

A: Well, we are still building out and developing #DateMe. So I have a feeling I’ll be busy with this show for a while. In addition to the stage version, I’m working on some writing and videos associated with online dating and the characters from the show. I see great potential for this show to live beyond the stage in social media and in the online world. Send us your awkward dating stories, and we’ll make an Instagram re-enactment video for you. Stuff like that. I want to connect with people.

In terms of other projects, I’m always writing and creating. I’ve written a couple pilots. And I have a couple other “experiments” in the works to tackle as soon as I have more free time. I’m fascinated by real people, and that’s what drives me. So my upcoming projects are quite different from #DateMe, content-wise. But similar in that they focus on human connection. I have a weird, little hobby of entering and winning online sweepstakes… and I’m going to do something with that in terms of writing and performing. But it’s another experiment, so it’s going to take some time.

#DateMe has been such a wonderful surprise and just keeps going. So I’m also just trying to take things day by day.