40 Days of Dating: NYC friends give love a chance, blog goes viral

Everyone has that one friend they wonder what it would be like to date. You share common interests — but is the chemistry there? Would it ruin the closeness you have now? Would all the annoying traits you know about them just multiply if things turned romantic? Many of us don’t bother taking the risk. Instead, we navigate the often-dismal dating scene online and in bars in the hopes of meeting someone new who happens to share our interests, values and desires.

But longtime NYC friends Jessica Walsh, 26, and Timothy Goodman, 32, decided to take that leap and participate in what they call an “experiment:” date each other exclusively for 40 days and document the experience online. The pair, who met in the graphic design community, decided not to publish about the experiment until after it was over in order to avoid being influenced by both their own perceptions and the public’s. They operated under a set of rules: see each other daily; have at least three dates per week; visit a couples therapist once a week; document everything daily; go on one weekend trip together; and no dating or sleeping with anyone else.

The 40 days wrapped up earlier this year, but Tim and Jessica’s daily observations are being published now. Keeping up with the daily developments of this budding relationship has fascinated readers — their blog 40 Days of Dating has gone viral with between 200,000 and 300,000 visitors per day, according to Goodman.

The world still doesn’t know whether Jessica and Tim continued the relationship, went back to being just friends or hate each other’s guts, but Metro interviewed them separately for the scoop on dating a pal — and letting the Internet watch.

How did you come to the conclusion that A.) You would try dating, and B.) You would blog about it?

Tim: I had a small dating idea last summer, but I didn’t really know what or how, and I had forgotten about it. It wasn’t until we were going to Art Basel in Miami back in December and we were waiting in the airport eating breakfast. Jessica and I have always been close and we have always bonded over our relationship problems. We are the single people in our group of friends and always made fun of each other for our issues. She was kind of heartbroken over a guy, I was dating too many women, and the idea of some sort of dating project came up.

By the time we got to Miami, we had conceived this crazy idea for 40 Days of Dating. Jessica and I have always been platonic. I don’t think we could have done this if we didn’t have a curiosity for each other in that way, but we had never gone there, and I don’t think we would have gone there. We were both nervous about risking a good friendship and ruining a dynamic in our group of friends. I always thought she was beautiful and talented. It felt like there was too much to risk, but the idea of using the experiment as catalyst to work on ourselves was really intriguing for us and we felt like it was a once in a lifetime opportunity.

Jessica: It all started last year on our way to Art Basel in Miami. I was pretty heartbroken over a guy. I had gotten out of a-long term relationship two years ago and ever since I had been trying to navigate the NYC dating scene. It was just not working out for me. Tim, on the other hand, has the opposite problem. He can never commit to a girl. And I am always the hopeless romantic. We had been making fun of each other for four years about how diferent our issues were. He had a good idea of a dating project and we thought maybe there is something here, where we could combine what’s going on with our lives into a creative project. We threw back and forth a lot of ideas on the plane. That’s when we had the idea for 40 Days of Dating. I was hesitant whether or not it would be interesting, but we did the experiment and recorded everything and after we started comparing our first few days, we thought people would be interested.

Have you blogged about past relationships?

Tim: No. I’ve always been interested in the idea of consumption and the idea of obsessiveness and including people. We are essentially changing the game of online storytelling.

Jessica: No, I have not. I did a lot of blogging around age 11 or 12, but since then I have never blogged.

Did you worry that having this new relationship made so public would add pressure to you both?

Tim: Yes. The reason we didn’t do it live is because we’d be influenced by each other’s answers every time and the public’s reaction. It was important to do the experiment first, not live. It was the only way we could keep a bit of sincerity. In terms of releasing it before, there were many concerns. There was risk involved both professionally and personally to put yourselves out like that.

Jessica: Definitely. The whole thing has been a huge risk, but I always felt in my own work things that were scary ended up being the best things I created. I can’t deny, I was scared sh—less. We both have reputations, jobs we love, great clients. It’s scary to be releasing this really public stuff. But people respond to honesty and to what is human. We are all just human so I did feel that people might connect with it. It’s been amazing to see the response that people have.

Knowing each other so well, what were your initial predictions about how dating each other would go? Did you think it would work?

Tim: For this experiment to be considered a success, it didn’t mean we had to end up together or not, it didn’t mean we had to garner press. The real point was whether or not we could help each other. I didn’t have any expectations. I didn’t go into it thinking maybe we would find love. I was open to it, just being an experiment. Maybe we could find love, maybe we would hate each other. I was nervous about it.

Jessica: No, I had no idea. Of course I know how he dates other women, but this was a completely different set of circumstances. I did find him attractive, we always did get along so well. So I did wonder if we could ever work, but I don’t think I ever would have dated him if it wasn’t under these rules we created that made me feel comfortable. I do know how he dates other women and is always flirting and and looking around and that’s not my style.

You blogged about your first time sleeping together on day 25. How do you feel about detailing your sex life online?

Tim: People thought this would ruin my dating life forever because they could go there and see all my issues. In a way, yes. But in a big way, it’s not. This is such a particular moment. It was an experiment. It’s not like we just met. I don’t know… It’s hard to say these are the details on my dating life. It was a dating experiment. I wasn’t too concerned about the sex stuff. Neither was she. As raw and honest as it is, we are trying to be tactful. We have a pretty good respect for each other. This isn’t an erotic novel. I just kind of mention it happened and that’s it.

Jessica: I went back and forth whether or not I should take that part out of the writing. But by then, after the first few days of posting raw and seeing the response we got, I felt like, “F— it, I’m just going to put it all out there and just going to go for it.” It’s a lot of pressure and it happened really quickly. It’s a little scary, but we are in it.

What do your parents think of the experience? Do you worry about them reading about your sex life online?

Tim: I think for both of us, our parents love it. Even my grandma loves it. Everyone has been really supportive. It was a big risk in terms of professionally with clients. So there was a major concern but you just have to trust your gut and take a risk. Maybe it will hurt some things, but it will help other things.

Jessica: I was a little nervous but they have always been extremely supportive of me. I did something very public last year for the announcement of my new design partnership where I posed nude. It was not the first time I have done something very revealing so they are already used to it. I knew they would be supportive of me. My dad doesn’t read the blog, which I think is good, but he still stands behind me and is very supportive of my decision to release this.

Was it strange for you to see a couples therapist so early on in a relationship – or do you think it’s been helpful?

Tim: It was extremely helpful and I don’t think we would have made it without her. The therapist was more about utilizing our time and seeing if she could help our problems together. The therapist helped what was happening between Jessie and I. But it was what always happens for us. We were filling the character role that we always play. At one point, we had to come to grips with that. Jessie realized she couldn’t keep pressing, because I was reacting to that in a negative way, and I realized I couldn’t run away. We had to work with that energy between us.

Jessica: I think it was extremely helpful and saved the project at several points. It was definitely strange at first. We went into the project naively, not having talked about a lot of major questions that should have been talked about. Are we actually interested in each other? Are we attracted to each other? The therapy forced us to confront these issues really soon, which is not easy. The therapy sessions were difficult and brought up a lot from our pasts, and forced us to examine it as reasons for issues we have today. After each session, it kind of forced us together in some way. I would highly recommend it to anyone. It can be helpful to people at any point.

What was your best date together?

Tim: I think one night we went to a jazz club and we had a really good time. At the time, I was willing to participate and let something go, finally. We had a really good time. And we were affectionate and intimate and had a great night. It was something that was more memorable. And I’m a huge jazz fan!

Jessica: I think it’s coming up [on the blog] in a few days. The hand holding experiment we just did. We basically attempted to hold hands for eight hours straight one day. We did all kinds of fun things together: brunch, we went to a bowling alley, we tried to do hand-stands in the park. It was just a super fun silly day and we literally never let go of each others hands, even when we had to go to the bathroom. We weren’t sure going into it, but it ended up being a really fun day.

What is it like to read each others perspectives for the first time before putting them online?

Tim: I read it a couple days before it goes live. We work together to make sure our columns kind of line up. It’s been difficult for both of us. In a way, it has been reliving the experience. There have been some rough parts. That hasn’t been easy for either of us. We will read something and think, “You really thought that? That’s not how I meant it.” It’s been interesting that way.

Jessica: We are still reading each new day, so I still haven’t seen it all. It’s been a roller coaster. The project itself had a lot of ups and downs. Reading his side, it brings back a lot of the emotions we went through in those 40 days. It’s been like reliving the experiment. On some days, it’s fun. On harder days, it’s not easy.

Were you expecting such a big following?

Tim: No, we knew that it was a unique idea and we had done our research. We knew we were potentially on to something. We didn’t do it for this and there were no expectations for this. It’s pretty crazy, all these people knowing about my issues. The outreach has been remarkable. So many people are connecting to our stories. Even people who aren’t single, who have been married for 10 years. Everyone can relate. We were not planning for that.

Jessica: It was a huge, huge surprise. I really had no idea. The human element is interesting, but I didn’t expect it to go nearly as big. I thought it would be our friends in the design community reading it, or our aunts and uncles. It has been a little overwhelming.

Can you tell us if you are still together?

Tim: I cannot. We just cannot give any spoilers.

Jessica: I cannot.

Follow Cassandra Garrison on Twitter: @CassieAtMetro


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