40 Days of Dating: An Experiment

by Jessica Walsh

  After this “boot camp” of self-reflection, along with the experiment with Tim, I feel like I am in a really great place. I’ve learned to let go, just be me, and go easier on myself. I’ve regained joy in my work and stopped caring about perceived expectations. The world doesn’t end when I forget to respond to a work-related email. The world doesn’t end if I take a weekend or two off or say “no” to meetings or hanging out with friends.

  The other day, Tim and I were discussing how interesting it is that the experiment started out as an attempt to solve relationship issues, but how it really helped us on other personal levels. The conversation reminded me that despite the drama around the project, our friendship is special. Many people only want to talk about the superficial stuff, but I can have deeper conversations with him about life and never feel any judgment.

  May 13, 2013: I went to Berlin with my sister on a business trip. After the conference was over we went to a nightclub called Berghain. Over the past few months, she’s been introducing me to techno and house music, and a few DJs she likes were there that night. I am not much of a party girl by nature. I am a homebody who would prefer to spend my Friday night in pajamas doing work or watching a TV series with a glass of wine. I’m glad she was there to pull me out of myself. When else in my life would I be dancing all night long in a dirty old warehouse space in Berlin? I had one of the most incredible nights of my life, full of perfect moments that I will never forget. We lost ourselves in the music. All insecurities went out the door. It made me appreciate being young, being single, and having the freedom to have these experiences that may not be so appropriate one day. At sunrise, they rolled the windows up in the warehouse, where we were all still dancing. My sister and I hugged and talked about how much we loved each other.

  May 18, 2013: I hadn’t looked at OkCupid in the weeks since that lonely night when I reactivated my account. However, a friend suggested I start dating casually. It can’t hurt to have a little fun. So I set up a date with a guy to meet at the Bourgeois Pig in the East Village for wine.

  On paper he looked pretty awesome, and it sounded like we had a lot in common. It was a disaster! We barely had anything to say to each other. I paid after one drink, politely left, and met some friends at another bar where we laughed about it.

  May 25, 2013: I had a date tonight with Zak, a guy I met on OkCupid recently. We met at a little bar in Williamsburg called Post Office. I couldn’t believe how easy and natural conversation was between us. He has a very laid-back and easygoing personality. He made me feel instantly comfortable and didn’t stop making me laugh. We were able to talk about so many topics, and it felt like we related on many levels. He is a cinematographer and seems to genuinely love his work. To top it all off, I am very attracted to him. The night passed quickly, and I left around 11:00 P.M. to meet up with some friends for a birthday party. After a few other disastrous dates this week, it was nice to finally have one good one!

  June 5, 2013: Tim is experiencing a lot anxiety about all the work we have to do to launch the 40 Days blog. He was driving himself a little crazy over it, so I tried to give him advice and take some of the load off his plate. That backfired: He said I was being too motherly but also that I was too accommodating. After a long string of misunderstandings and an angry phone call, I ended up getting a little worked up myself. I just don’t understand our communication breakdowns. We never used to fight like this before we dated. Anyway, he wrote me a nice email, and we both apologized about it in the morning.

  June 10, 2013: Tim and I have been going over the details of launching our diary entries on the website. It’s been a little stressful creating the website with him. I talked to a friend about it. She observed that it’s funny how Tim and I have fairly stereotypical gender-specific issues in relationships, but when it comes to other aspects of life, like my work, my personality is much more typical of a man. I can be very direct about what I want, I’m less emotional, and I talk about issues head-on. Tim, on the other hand, can be very sensitive to my criticism and indirect about what he wants. He keeps things that bother him to himself and lets them fester until he’s so frustrated that they suddenly boil up and he gets angry with me.

  Meanwhile, I’ve been texting and emailing a lot with Zak. Our conversations have been lighthearted and funny, and they’re a nice distraction from all the drama with Tim. Zak is pretty persistent about keeping up the conversation, and keeps texting that he wants to hang out again soon. I want to see him again, but I’m purposefully trying to slow things down. I don’t know if I am ready for something serious again.

  June 15, 2013: I was telling Tim about this care package I received in the mail from some guy I’ve never met. The guy found out my favorite foods from my Facebook profile and sent me a big box of avocados, chocolate, and coffee. There was also a USB stick with a presentation he designed that contained mood boards of options for our first date. It was quite involved, made me feel obligated to say yes to a date with him. But I canceled when I found out I was going to Barcelona for work. He then proposed we meet up in London, while I was over there. Here I was thinking that I moved fast! I told Tim about it:

  Tim and I decided to meet up later at a cocktail party. I got pretty tipsy, and I was wearing five-inch high heels, and at one point in the night one of my heels broke off. We were laughing at my waddling around this very fancy venue like a penguin. At the end of the night Tim had to practically carry me out of the party. We shared a cab home and were having a great time. I still care for him deeply. There was a moment when I wanted to kiss him, but I held back. I was drunk, and I knew I’d regret it later. We’re not right for each other, and I don’t want to complicate things more than they already are.

  June 18, 2013: A few days ago I met up with Zak for a second time; we had a brief lunch date. Last night we continued the conversation at a bar in Williamsburg. His honesty and forwardness with intimate and emotional details about his personal life were refreshing. I felt like I could pretty much tell him anything without any judgment. He seems at peace with himself and with life, and he has such a great energy. There doesn’t seem to be any sort of “front” or “facade” with him—he wears his heart on his sleeve and is confident about it. The most striking thing about him is how relaxed and calm he is. We talked about how much we both hate drama. I slept over at his place. This morning we went to breakfast at a cute little place called House of Small Wonder and were talking about how we were overdue for a trip to the beach. He told me about this beautiful spot in Mexico called Tulum that isn’t too touristy. Zak joked that we should just run off for the weekend, and I said, “Why not?” I was joking, but next thing I know, he pulls out his iPhone and buys the plane tickets. I love how spontaneous he is! Why is it that I meet an awesome guy when I’m not looking for one?

  June 19, 2013: Parsa emailed me this note today. He’s the ex-boyfriend who broke my heart last December and left me completely confused about what went wrong. I blamed myself for everything. He made me question myself and how I approached relationships. It was part of what drove me into the dating experiment with Tim. Even though it’s been over six months, it was really nice to hear from him and get clarity on what went wrong. I finally feel like I have some closure on that relationship now. It also was a nice reminder that it is never too late for apologies. I probably owe a few to guys I may have unintentionally hurt in the past.

  June 21, 2013: I received this email from Tim the other day:

  Afterward we had another conversation on the phone. I asked him why he was changing his mind now. He said he felt like he had fucked up. He said he truly wants to try to date me again, but he sees now that he waited too long and now I’m gone. He said the idea of a relationship with me always scared him. He said for years he felt like I was “a girl you marry, not date,” and that this idea put too much pressure on him. He’s sure, now, that he wants to try dating me. I probably would have tried dating him again if he had told me this sooner and with more confidence. Life is all ab
out timing, and it is not on his side. Zak, on the other hand, has let me in closer emotionally in only three dates in ways that Tim never did. There was always a barrier with Tim. This gives me more confidence that Tim and I were just not the right match. Even if we had tried dating again, I don’t think we would have lasted. I hope with all my heart that Tim finds someone he is completely comfortable with, who he can let his barrier down with. He deserves that.

  June 30, 2013: I jetted off to the beautiful sandy beaches in Tulum, Mexico, with Zak this weekend. I didn’t tell Tim I was going, even though he kept asking me what I was doing during the weekend. I felt bad since he had told me he wanted to get back together. I didn’t want to hurt him by rubbing it in his face about Zak. The trip was truly magical. The landscape in Tulum was almost surreal. In the mornings we’d do yoga and hang out on the beach together. In the afternoons we drank cocktails, explored the Mayan ruins, and went cave diving in the cenotes. At night we stayed up for hours talking about all aspects of life. While we met only a month ago, he’s been very forward about his fondness for me. He told me how he never expected to meet someone like me. That he’s been searching for a long time, that he had almost given up.

  July 4, 2013: For the Fourth of July I went to a dance party on a Brooklyn warehouse rooftop with Zak and my sister. We danced all day long until the sun set behind the Manhattan skyline. Later we sat by the waterfront in Brooklyn, listening to music and talking. Zak turned to me at one point and said, “One day, eventually, you’re going to get mad at me. I want you to remember how happy and how perfect everything is in this moment, and I hope you’ll find it in your heart to forgive me.” I can’t even imagine ever being mad at this guy. He is so perfect for me, and I’ve never been happier. I told Tim I was falling for Zak, and he did not seem very happy about it. He warned me to be careful and not let another situation like Parsa happen again. While I am aware that love makes me vulnerable, I don’t want to hold on to fear and let it run my life. I know Tim sees my ability to love people without much reservation as a weakness, but I believe he is mistaken. The vulnerability that love requires, the complete openness and trust—this is not something everyone can handle. You need strength to be vulnerable. I believe that running from it or putting up walls only makes you scared, not strong.

  July 11, 2013: Tim and I launched our journal entries to the public a few days ago via our blog, www.fortydaysofdating.com. I have a bit of anxiety about it. I am pretty open and honest about my most intimate thoughts and feelings during that time. I wonder what my family, clients, or even work colleagues will think about it? And I worry about how Zak will react when he reads the intimate details about my relationship with Tim. I hang out and talk with Tim all the time, and I wonder if that will start to bother Zak once he reads about what happened between us. On another note, Tim continues to tell me about his dating escapades. He’s clearly frustrated with himself for falling back into his old patterns with women.

  July 15, 2013: The response to our 40 Days blog has been crazy. We’ve had hundreds of emails from the press wanting to do interviews, and today we got our first emails from producers in Hollywood about turning the experiment into a movie. I am completely shocked. I never imagined our little dating story would go viral. The attention has been exciting but overwhelming. I feel like there aren’t enough hours in the day to respond to everyone.

  July 23, 2013: I got this text from Tim:

  The more I think about it, the more frustrated I become. I can’t figure out if he is just playing games or if he really believes this. I don’t know which is worse. If he’s making this up in one last attempt to get back with me, it’s not going to work. Even if he does believe he feels this way, what purpose does it serve now? He knows I’ve fallen for Zak, so what’s he doing? Is he trying to sabotage our friendship? Some things are better kept to yourself. I’ve always believed words are cheap and it’s a person’s actions that speak the loudest. Tim never did anything to show me these feelings, and I just don’t understand where this is coming from right now.

  July 29, 2013: Lately it has become more and more difficult to work together with Tim. We have so much work to do on the artwork and videos for the blog, and this is on top of our regular work. Ever since launching the site, we’ve been bombarded with fan mail and interest from Hollywood. I am doing my best to do as much as I can, but it never seems to be enough for Tim. Maybe he’s frustrated that I didn’t reciprocate the “I love you” message. There have been angry texts, dozens of emails in the middle of the night, and frustrating phone calls between us. I told him that if we couldn’t work together professionally, I was going to have to quit the project. I won’t let a blog ruin my life or our friendship. He wrote back suggesting that we go to therapy again. As crazy as it sounds, I am willing to try anything if it makes things right between us. We made an appointment for a few weeks later.

  August 3, 2013: Things are more strained with Tim. There is so much pressure between my work and the blog and finding time for Zak, and Tim makes me feel so guilty that I can’t do more. Agents have been pursuing us because of the blog, and we are trying to decide who to go with. We do not see eye-to-eye about certain things, and we’re still having constant communication breakdowns. I woke up in a sudden panic at 4:00 A.M. and I couldn’t breathe. I felt like everything was out of control and falling apart. Zak calmed me down, and helped me slow my breathing, but my mind wouldn’t stop racing. I changed into my running clothes and went running up and down the West Side Highway for five hours. Five hours. I’ve never run so far or for so long in my life. I wanted to wear myself out to the point that there was no energy left for worry or stress.

  August 4, 2013: Zak was worried about my panic attack, so he booked us a room at the Standard Hotel for the weekend. Being with him was just the calm I needed to unwind and relax, away from the pressures with Tim, the lawyers, and the media. Every experience we have together continues to come with such ease and joy, and the relationship continues to get better with each day. Like me, Zak is a kid at heart: We had lots of silly moments that weekend, like romping around the hotel wearing fake moustaches and ridiculous outfits, and spontaneously dancing in the middle of the lobby.

  Tim called and became angry when he found out I was at the Standard with Zak. He couldn’t believe I was taking the weekend off when we had so much to do. I know it’s unfair of me when he is doing so much, but I tried to explain to him that I needed a break for my own sanity.

  August 5, 2013: Today, Zak and I sat on the rooftop of the hotel overlooking the New York skyline. I was telling him the most embarrassing story from my past, and he stopped me mid-sentence and told me he was in love with me. I couldn’t wait to say it back. It’s hard to put into words my feelings for him; I am not even sure there are words for those feelings. If there are, I certainly could not say it in a concise way. The best I can come up with is that it feels like we share a secret, like we understand each other in a way that no one else does. We see the world in a way that no one else sees it. Everything in life seems possible with him, like we could take on the world as long as we are together. He gives each new day so much excitement and meaning and joy.

  August 12, 2013: Tim and I agreed to be in Los Angeles today to meet with a production studio about making a TV show based on our experiment. We also were meeting with potential agents who would represent us for film and book deals. I wanted to leave a day early since Zak was already there filming a movie, and I hadn’t seen him in a week. When I mentioned taking an earlier flight to see Zak, Tim flipped out on me. He cringes every time I say his name. He said the only reason I wanted to go to LA was to see Zak, and that I didn’t care about him or the experiment any longer. That is so hurtful to hear. Everything is so complicated now, and I wish Tim would cut me a little slack. I try not to mention Zak, but it’s difficult to never mention someone who is a huge part of my life. I wish this hadn’t gotten so messy.

  August 16, 2013: These past few weeks have been a complete whirlwi
nd. Tim and I have been nonstop in interviews, photo shoots, meetings, and magazines. It’s crazy and humbling that our little blog is being read by millions of people around the world. I have mixed feelings about all the press and attention. In part, I am thrilled that our project has reached and touched so many people. It’s unbelievable to read some of the letters our readers send us and see how it’s changed their lives. Some people say that our project inspired them to make positive changes in their own relationships, inspired them to seek therapy, or inspired them to date that friend they were always curious about. At the same time, I am overwhelmed. The other day I was recognized by strangers six times in SoHo.

  I was stressed about it and went to the gym, where a girl tweeted that she was “working out across from the forty days of dating girl.” Another person tweeted that that he saw me with Zak and that I was “cheating on Tim.” I never realized how much I value my privacy until now.

  August 18, 2013: Tim emailed me this morning and I didn’t know what to write back. He knows I love Zak, and I wish he had more respect for that. I hope he meets an amazing girl soon, someone who makes him realize how wrong we were for each other. I don’t want there to be any resentment or jealousy or disappointed feelings. I want him to be happy.

  August 22, 2013: Today we had a session with the therapist we went to during the experiment. Tim said he thinks I am angry because he “rejected me” in Disney World. Rejection is the last thing I feel right now: I feel like I dodged a bullet. I didn’t tell him that, though. I admitted that while it’s true I may have tried dating Tim again if I hadn’t met Zak, I still didn’t think it would have worked out between us. We also talked about my frustration over his declaration of “love” for me a few weeks ago. It hurts me, because I am in a loving relationship with someone else, and I wish he could accept it and be happy for me. I just want to mend things with him. I have to remember that we are under extraordinary pressures in utterly unique, some might even say bizarre, circumstances. We need to stay strong, support each other, and work together as a team.