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40 Days of Dating: An Interview with Jessica Walsh and Timothy Goodman

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When a friend sent me the link to fortydaysofdating.com a couple of weeks ago, I thought, Urgh, stop sending me links to online dating sites guys. But then I read it, realized what it was, and kept reading it until one in the morning. 40 Days of Dating is an experiment conducted by graphic designers and close friends Jessica Walsh (business partner to Stefan Sagmeister) and Timothy Goodman. Both troubled by unsuccessful recent relationships, Jessica and Tim decided to see if they could change their dating habits (Jessica: hopeless romantic; Tim: serial dater) and date each other exclusively for 40 days. An overview of the rules: they had to see each other every day, there had to be at least three dates a week, they must fill out a questionnaire about their experiences at the end of each day.

Would they fall in love? Would they hate each other? Would they have sex? If they did fall in love, would it really just be Stockholm Syndrome? And would they stay together after the forty days were up? I had so many questions, including "Should I try this with my best friend?" The answers to all of these (except maybe the last) have been hinted at, explored with total honesty, and illustrated in beautiful typography contributed partly by Jessica and Tim's friends, over the past several weeks. While the project was carried out in full this spring, the results have been published daily this summer. The final four days will be rolled out starting on September 3rd and I am DYING to know what happened during Tim and Jessica's final weekend at Disney World—so I sent them some questions to probe (without giving too much away).



Jessica Walsh

Alice Newell-Hanson: What is the best date you've ever been on?
Jessica Walsh: The best date I ever went on was to Tulum, Mexico. It was an amazing and spontaneous third date. We spent the weekend drinking spicy cocktails, getting Mayan clay mud massages, eating amazing food (the restaurant Hartwood is to die for), and snorkeling in the cenotes.

What is the worst?
The worst date I've ever had was at Freemans. The food there is amazing, but there is always a one or two hour wait as they don't accept reservations. By the time we sat down to eat I had detailed accounts of every past relationship he's ever had. He spent dinner talking about how amazing and successful he was, how lucky I'd be to date him, and what an amazing boyfriend he'd be to me! He barely let me get one word in the whole dinner. He ordered an enormous amount of food, and I only had an appetizer as my stomach was in knots. When it was time to pay, he fumbled around in his pockets—he forgot his wallet!—and I had to pay the $250 bill.

Please describe your favorite date with or gift from Tim.
My favorite gift from Tim is something he gave me on Day 40 of the experiment, so I can't tell you yet as it will be a spoiler! My favorite date was the hand holding day!

What do you think makes dating in New York in 2013 especially easy/difficult?
NYC is both an easy and difficult place to date. On one hand, there are so many wonderful guys here, and online dating makes finding them very accessible. But on the other hand, everyone is too busy and thinks they can do better.

We've become so used to sharing our personal lives on the Internet. Were there certain things you were nervous about sharing?
Of course. I was nervous about releasing the entire thing. I had no idea if people would like it or find it intere

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