After Forty Days: Jessica Walsh on Love, Work, and Life as a Viral Phenomenon

Her relationship experiment—'40 Days of Dating'—was viewed by millions. Two years and one happy ending later, New York designer and internet star Jessica Walsh is en route to Portland.

By Fiona McCann July 28, 2015

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Photo credit Zak Mulligan

In July 2013, two young New York designers published their romantic experiment online. Jessica Walsh and Timothy Goodman were good friends who, finding themselves single at the same time, decided to embark on a dating experiment. As designers, they documented the entire process. The result, the blog 40 Days of Dating, has been seen by over ten million people and counting, becoming an internet sensation and catapulting Walsh and Goodman into the limelight.

Two years on, the two friends have closed the book on their own experiment—with a literal book, 40 Days of Dating, released earlier this year by Abrams of New York—and Walsh has found her own happy ending. She's in Portland this Friday (July 31) to talk about work and play, and caught up with Portland Monthly ahead of time to dish on creativity in life and love, and whether dating your friends is ever really advisable.

You’re in Portland to talk about using play in work. How does play inform what you do professionally? 

The heart of much of what we do as creatives is discovery through experimentation. Often the best ideas come out of spontaneous play. I think play is a mindset, where I allow myself the space and time to experiment and take risks without being afraid of failure. It’s during this time that I create the most exciting work because I am allowing myself the space to push the boundaries of my work. If you don’t allow yourself this form of serious play, you often end up falling back on existing styles and techniques you know have worked for you or someone else in the past.

Was that what 40 Days of Dating was about? Did you embark on the project from a creative/professional standpoint or as a personal project?

40 Days of Dating is a project I did with a good friend of mine, Timothy Goodman. . . It is not unusual for creative people to bring their lives into their work. Songwriters, film makers, journalists and artists have been doing that regularly for a very long time. Graphic designers tend to shy away from the personal or using design  for expressive purposes. Designers have the skills and tools to communicate with a wide audience. I personally am most attracted to work that has a personal angle, and clearly comes from someones heart. To me content creation and expression through design is just as (if not more) important to me than designing other people's content. I want to continue to spend more time on more personal work like this.  

The project had some interesting professional and personal overlap – was that a comfortable space for you?

Not at first, to be honest. We were very nervous about releasing the blog as it has many intimate details about our emotions, our dating history, and even our sex lives. However after seeing the feedback, it’s given me a lot of confidence to assert my personal stories and voice into my work more often. James Joyce says: “In the particular is contained the universal," and I really believe this is true. While many of us try to distinguish ourselves as individuals, our emotions are largely universal, across all ages and cultures. By opening up about them and being honest, people were able to relate to us.  I find that the work I’m most interested in doing is inspired by the human experience. 

 Did it help your work in any way?

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Photo credit Zak Mulligan

40 Days of Dating made me rethink my career and the way I work. Since the launch we've had thousands of people write us about how our story touched them, made them laugh, made them cry, and in some cases even helped change their life. It's amazing and humbling to hear that kind of feedback about something you put out in the world. It reminded me that content creation and expression through design is just as important to me as designing other peoples content. I will always enjoy the challenge of our client work at the studio, however I am now focusing at least 25–50 percent of my time on developing my own ideas, websites, apps, or writing. I’m finding having this balance doesn’t take away from the commercial side, but helps with it as it keeps me passionate and inspired.

 How did the book come about?

I think what happened after the experiment ended is so much more interesting than what happened during the experiment. So we kept diary entries for a year after the blog ended. The book contains these diary entries much like the blog did, where you can read our entries side by side. It also contains a lot of other information about love and dating. We wanted to wrap our story into the larger picture of today's dating culture and how we got to where we are. We are byproducts of our generation: 40 Days of Dating would have never happened if we were alive at a different point in time.

Are you and Tim still friends?

Yes! We’re best friends, even closer then before. This project and experiment taught us so much about life, love, and each other. While we weren't meant for each other romantically we have a great friendship and creative collaboration. We’re currently working on a new project which will be out later this year.  

What advice would you give a couple who are friends and considering dating?

We only have one shot in this life, so if you are both curious, go for it! The worst that can happen is that it doesn’t work out, you can always go back to being friends.

How has life been since 40 Days? Did it lead to new creative opportunities? Did it help from a relationship standpoint?

They say you can’t chase love and perhaps it's true. During the experiment I was stressed out about relationships, working too much, and not living a healthy lifestyle. The experiment (and therapy) helped me realize I just needed to take care of myself. I was in the best state of mind after the experiment ended. I was relaxed, balanced, and carefree. I approached dating that way as well. It’s interesting that as soon as I stopped looking for the right person, I ended up finding the love of my life a few months after. We just got married six months ago!

Knowing what you know now, what advice would you give pre-40-days Jessica Walsh?

Don’t worry so much about everyone else.


Jessica Walsh is at Revolution Hall on Friday, July 31.   

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