Interview with the Creators of Forty Days of Dating

Meet Jessica. Your not-so-average graphic design bad-ass who has a knack for falling for guys too quickly. Really, her issues with relationships are something we can all relate to. Imagining a future with someone only to find yourself without them down the road

Meet Timothy. Another graphic design extraordinaire living in the streets of New York – but unlike Jessica, Timothy’s relationship problems result in a steady stream of women. Depending on how you look at it, not really a problem – until you realize you want something more. 


Jessica and Timothy have been close friends for four years. You put together two creative people who have been a constant in each other’s lives for years and are tired of the monotonous dating scene offered in New York, and what do you get?

Forty Days of Dating is part social experiment, and part design project. In an attempt to explore our habits and fears in relationships, we decided that “dating” each other for 40 days could be a way to explore this. Having the boundaries of a project allowed us to take on that challenge. It really was a once in a lifetime opportunity.”

So why should we care about two people who also can’t seem to make sense of the complex word of dating? Because they are doing something that many of us don’t: push past the awkwardness of the first/second date and actually strive to get to know the person they’re sitting across from. As Jessica and Timothy say:

It takes 40 days to break a habit. So can they change their dating habits… together?


– How did you guys come up with “Forty Days of Dating?” 

It was a small idea Tim had about a year ago, but he didn’t really know the ‘what’ or the ‘how.’ Then one day on our way to Miami for Art Basel—when Jessie was heartbroken about a guy, and Timothy was dating too many girls at once—it became crystal clear. We ran with the idea, and it really became something entirely different after that. We started throwing crazy, nutty ideas back and forth during the plane ride, and by the time we landed in Miami we had a pretty elaborate and crazy plan for “40 Days of Dating.”

– What do you think is the biggest struggle men and women face when it comes to relationships? 

Tim: Commitment.

Jessica: I  think dating in NYC is harder than in some other areas. Part of it is the numbers, there are just so many wonderful single women here. While I think dating sites like Match and OKC are great, they have some downsides, I think they’ve caused so many men and women to take it for granted when they do find someone special they connect with, because there are so many other great options. Many people fall into the trap of always thinking  they can do better. And everyone is so busy and career focused, that even  if you do find someone great,  it’s often hard to develop something deeper when you can barely squeeze them in your calendar.

By Timothy Goodman

By Timothy Goodman

– Was it weird/awkward to begin “dating?” 

The first date was not so awkward, it felt like going to dinner as friends like usual. It wasn’t until the second day, when we went to couples therapy, that things became very awkward. Our therapist Jocelyn started bombarding us with really difficult questions we were not prepared to face.

(*Spoiler alert: Read about Jessica’s experience dating a Persian guy).

– What was the goal of the experiment? 

The goal was to explore our relationship issues together, since we have opposite problems. Perhaps we could meet in the middle. Perhaps we’d hate each other. Perhaps we’d fall in love. We had no idea going into it what would happen.

– Who came up with the rules? 

We came up with them together. There were certain ones Tim insisted on to help with his own issues, such as seeing each other every day. There were certain ones Jessica insisted on, such as the couples therapy. We’ve both been to therapy and had great experience with it. We thought this would be a great way to have a third party mediator who could help us with our goals for self-growth. The therapy saved us on numerous occasions when we wanted to quit.

– Rule #6: You can’t see/date/hook-up with anyone – was that difficult to follow? 

Tim was very tempted, when you read the blog posts you can see his temptation to flirt. It was not difficult for Jessica.

– What is the most valuable lesson you’ve learned through this experiment? 

Jessica: We learned numerous things. One important thing I learned is that I have to take care of myself before establishing a healthy relationship, first. I had numerous health problems during the forty days and was very stressed out.

The experiment sent me over the edge, and I completely changed my lifestyle around.

I am now eating better, working out, and feeling great.


By Jessica Walsh

– Did the experiment work? 

Certainly. However, we never defined what success might mean or set expectations. It was an experiment, a study, a chance to get a glimpse into our dating habits and fears with the help from each other. When else can you do that in life?

The project could be considered successful if we came out of it as more aware individuals, regardless if we feel in love or not.

– What did your friends say about this or did you not tell them? 

Tim: Surprisingly, some of our mutual friends weren’t so keen on it. They thought I was either going to hurt her, or that I was just trying to sleep with her. Which is ridiculous, because if that was the case, I would have already tried to sleep with her!

Jessica: While we were on that Miami trip, we told our friends about it. One of our friends started crying at the dinner table. They just didn’t want us to ruin a great group dynamic. They thought that Tim just wanted to sleep with me, and that I just wanted a relationship with him.

– What’s next for you? 

Tim: It’s always been very important that I bring my own voice and sensibilities into my work.

A project like this, where we essentially sacrificed our personal lives, was incredibly rewarding because it went beyond design. 

I’ve always been in tact with my relationship issues, and I’m fascinated with human habits and the things that make us tick when it comes to interpersonal relationships. Being a designer became a vessel for how to tell our story.

Jessica: My business partner, Stefan Sagmeister, has been exploring the theme of happiness through his documentary film, “The Happy Film.” I’ve always admired the human and self-exploration aspect of this work. As a designer, I am driven to create emotionally driven work that can touch people in some way. Relationships are such a big part of existence, and they effect our lives so deeply, so I wanted to learn more about this topic and myself. It’s wonderful to be in a field where I have the skills to communicate with people visually, and I try to use that to my advantage. I’d love to do more personal projects like this in the future. 


So what happens? Do they fall in love or is this just another hook-up in the city?

For the experiment, Jessica and Timothy each complete a questionnaire about their day. How often do you get real insight in what each person is thinking in a relationship? No sorry, Jersey Shore doesn’t count. Make sure you check it out – they have three days left in their experiment!

Read Forty Days of Dating

Tweet @JessicaWalsh

Tweet @TimothyOGoodman




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  1. i choked on my coffee when this post said that the dude has a “steady stream of women”. if this dude has a steady stream of women, i am going to fuck everyone in nyc. LOL. this cant be real

  2. Obviously Tim is a jerk with no control over his lust and Jessica is a romantic freak. We all know where it’ll end. They fuck and he breaks up with her and she gets down.

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