40 Days of Dating




Jessica Walsh is a hopeless romantic. Timothy Goodman is a commitment-phobe. Friends for years, they found themselves mutually available and decided to date for forty days, to “explore and hopefully overcome their fears and inadequacies.”

Designers by trade — Walsh is a partner at design firm Sagmeister & Walsh, Goodman is a freelancer with clients such as The New York Times, Ace Hotel and Mott’s — they were familiar with the seemingly oxymoronic method of imposing restraint and limitations in order to inspire creativity.

They approached 40 Days as a design experiment, even establishing six dating ‘rules’: daily rendezvous’, three dates a week, an agreement to keep it monogamous, weekly couple therapy sessions, and a weekend getaway — all documented on fortydaysofdating.com.

The experiment acts as an outlet for not only romantic but creative expression. The site itself boasts an exuberant aesthetic; color, animation and exclamation marks akimbo. As an outspoken enthusiast of play and experimentation in her work, Walsh saw 40 Days as an opportunity to showcase multiple creative mediums. Video, illustration, and animated typography by other renowned designers are combined with a daily questionnaire. It was their mutual penchant for risk and uncertainty in professional endeavors that drove them to embark on the project together. “I’m easily bored, so I’m constantly pushing myself to grow in all aspects of my life and work. This means I’m constantly seeking new things to learn, and new types of creative outlets,” Walsh says. Goodman describes himself similarly: “When it comes to my work, I love the idea of not [knowing]. I love that challenge.”

The project’s artistic success aside, it is the personal nature of the content that makes 40 Days so arresting. “It’s reinforced that people appreciate the human element. People like imperfections,” Walsh says. And the opportunity to show imperfections are ample: the website chronicles the demise of past relationships, therapy session post-mortems and video interviews that watch more like a game of truth or dare (without the latter), elevating 40 Days from mere blog to, as Goodman puts it, “web reality”. “It’s about finding something that’s particular, and finding what’s universal about that [particularity]. That’s why this worked. It was something that was so personal to Jessica and I, [but] our story isn’t unlike a lot of other people’s.”

“I’ve always wanted to touch people through my work, [so] in this way it’s been a success.” Walsh says. She cites her business partner Stefan Sagmeister’s The Happy Show as an inspiration to reflect on her own well-being. An interactive installation piece that walks its viewer through Sagmeister’s journey and attempts to “[train] his mind” into achieving happiness, its parallels with 40 Days as examples of emotional experience design are clear.

Beyond the project being a fun outlet for creativity, friendship and the possibility of romance, the pressure for accountability provided significance and meaning to the situation. “[That] really pushed us to do the experiment and not just date, because that wasn’t the only point. We had to stay sincere with the idea,” Goodman says.

The most apparent reason for 40 Days’ success comes from Walsh and Goodman’s differences. One is the romantic optimist, the other the pessimist; one emotionally forthcoming, the other unavailable; one with a need for control and tendency to define, the other laissez-faire. And there justifies the adage “opposites attract”: as painful a cliché as it is a truth.

Goodman says this polarity has had a positive effect on him, both personally and creatively. “This experiment has definitely changed me as a person. I’ve realized I want a relationship, and have come to grips with my past — certain decisions I’ve made, and I’ve owned up to that,” he says. For Walsh, however, it isn’t so much how different her collaborator is from herself that fuels her creativity, but their sincerity and intent: “I like to work with people who are nice and have a good heart, regardless of whether or not they are different or similar to me personality wise.”

The forced reflection of 40 Days permits itself as a design experiment of human relations. Both Walsh and Goodman bring up various theories that the experiment put into practice: familial influences, the Myers-Brigg personality indicator, Robert Moore and Douglas Gillette’s theories of masculinity and femininity as illustrated in the book King, Warrior, Magician, Lover: Rediscovering the Archetypes of the Mature Masculine. Walsh, describing herself as “intuitive, passionate and persistent”, sees the commonalities between her personality type and her creative approach.

The admiration Goodman has for Walsh, who has achieved remarkable success at the mere age of 26, is palpable; even romantic. He rephrases Moore’s and Gilette’s theory in a far more poetic manner through a quotation of Joseph Campbell’s: “She is the totality. He is a protecting factor, the agent of her power.”

More than anything else, it is the capacity for self-reflection in 40 Days that makes it a success. Every facet of the experiment calls for your projection of your own romantic self. Consider the immediacy of your judgment after reading the day’s installment: whether it’s a cynic’s eye-roll or an optimist’s ooh and aah, you’re confronted with the dichotomy. In our collective reaction to 40 Days’ design, there is consequent need to take a side.

As today’s final post reveals, Walsh and Goodman didn’t work out. A sweater on day 39 piqued an argument that surfaced their inherent differences, leading way to surrender. Walsh, ever the light-seeker, punctuated her final answer with plenty of hope and faith for the future. Goodman was a man resigned. For many, that ending cinches the experiment’s failure, though that would be a sadly myopic stance.

Read about the project at fortydaysofdating.com 

Forty Days

the author

Caroline Leung