Jessica & Timothy

When we spoke with Timothy for his digital interview, the project had already debuted. He told us, “Doing 40 Days of Dating was a risk for both Jessica and I, personally and professionally; it’s one of the most comprehensive risks I’ve taken. In many ways, it has clearly been good, but was doing it good for my design career? I don’t know yet.”

Now that 40 Days is over and you’ve both had time to reflect, how did the project affect your careers and lives?

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

Timothy: I recently heard a great quote by Lena Dunham. She said, “By sharing your own stories, you’re essentially performing a kind of activism that’s very important…by sharing things that are close to you, you will connect to other people who feel alone in the world.” 40 Days has torn down a wall that I’m no longer interested in having up as a designer. I’ve never felt more vulnerable as a human, or as a designer, and I’m interested in sharing more of that experience. Jessie and I found that so many of our own experiences and fears are the same as other people’s, and I want to continue to connect to people and start a dialogue through my work. I’ve also been writing more about my personal life through a series I call Memories of a Girl I Never Knew, which I post on my Instagram. It’s been amazing to see how much it has resonated with people, and I don’t think I would be sharing that kind of stuff with such ease if it wasn’t for 40 Days.

What was the most important lesson you learned about relationships, romantic or not, from the project?

Jessica: The most important lesson I learned was to relax, be myself, and not worry so much about dating or finding the right person. People say you can’t chase love, and perhaps that’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 that I needed to take care of myself. When the experiment ended, I was in the best state of mind: I was relaxed, balanced, and carefree. Coincidentally, as soon as I stopped looking for the right person, I found the love of my life a few months later—we just got married two weeks ago!

Timothy: 40 Days and its residual effects have enabled me to be honest with myself about finding a relationship with someone who’s worth it and given me a greater capacity for vulnerability. With vulnerability comes the risk of failure—I’ve really gone for it a couple times with women I’ve liked, but, unfortunately, nothing has worked out yet. Do these failures suck? Hell yes. Am I scared? Yes. But I won’t be discouraged.

There’s no such thing as being fearless. I don’t like it when I hear people say that. We’re all scared, and none of us know what we’re doing. I don’t even want to know! The good stuff comes from the unknown, from being lost, from having your back against the wall. If I can walk that tightrope, then maybe I can feel more alive and find more meaning in my work. If we have an idea about how to inspire or be inspired, then we can begin to connect to people, and I think connecting to someone through my work is one of my true joys.

You teamed up with Abrams to write 40 Days of Dating: An Experiment, which debuts January 20, 2015. What’s in the book?

Both: After everything, the number one question we received from fans was: What happened after Day 40? That question will finally be answered! While the book provides that answer, it also covers much more through excerpts taken from the journals we kept during the year following the experiment, which reveal everything that happened between us. The book also includes Q&A’s about our childhoods and our lives before we met, our histories of dating and a dating map, worst date stories, and essays about love and relationships from different people, including Lorene Scafaria, the screenwriter for our movie. And there’s tons of new artwork and much, much more. You’ll also find that we’ve added an extra layer to the blog in the margins: our personal remarks on each other’s entries. This was a real labor of love for us.

What’s next for 40 Days, and what’s next for each of you?

Both: We have continued to collaborate via the 40 Days book and our small personal project, Quotes on Shit. We are also currently halfway finished with another very robust experiment that uses our personal lives as a catalyst to tell a story—look for it this summer! The movie with Warner Bros. is still in process, and we’re hoping that the script will be approved soon. Overall, we want to continue doing personal projects that will create a dialogue with a larger audience.