40 Days of Dating: An Experiment

by Jessica Walsh

  I always tell my students that they should approach design as a practice rather than a profession. We can’t forget the place we started from, and we should always be looking for new ways to connect with people through our work. I recently re-watched It Might Get Loud, a documentary that I love. Jack White talks extensively about the reduction process in music and art, and how hard it is to find the truth in its simplest form—something I’m always trying to work at. He goes on to say, “Technology is a big destroyer of emotion and truth. Opportunity doesn’t do anything for creativity. Yeah, it makes it easier, and you can get home sooner, but it doesn’t make you a more creative person. That’s the disease we have to fight in any creative field: ease of use.” He also wrote one of my favorites, a fifty-second song entitled “Little Room.” It consists of nothing more than vocals and drums. For me, the lyrics tally up one of the critical difficulties in the creative process.

  DAY THIRTY-SEVEN: APRIL 25, 2013

  Jessica Walsh

  Did you see Timothy today? Yes.

  What did y’all do together? It was our final therapy session together. While often difficult, I do love the therapy sessions. I think anyone can benefit from therapy, no matter what the reasons or goals. Go with your lover, go with your husband, go with your boyfriend, go with your best friend. Take your pet! It’s amazing to shed light onto your day-to-day insights, if only to bring more awareness to your actions and choices.

  Did anything interesting happen? Jocelyn asked us what we wanted to do now that the project was ending. Tim said he really does want to date me exclusively, he just couldn’t give any marriage commitments yet. Wait, what? Marriage?! Where did that thought even come from? Still, I agreed that I’d also like to try dating him outside the context of the project.

  Jocelyn brought up how Tim was “in control” during the entire experiment. She asked me to analyze why I became so submissive around him. In previous relationships things were much more balanced, or I often had more control. Throughout this experiment and relationship, everything has felt like it is on Tim’s terms. Part of me always feels on guard around him too, as he can be sensitive and I am afraid something I might say might set him off. It’s interesting how we can be (or become) such different people depending on whom we’re with, or on the situation we find ourselves in. No wonder relationships are so difficult. It’s not easy to entirely understand yourself, let alone the person you are with. We are all constantly growing and evolving.

  She also challenged me to think about why it was so difficult for me to feel so out of control during the experiment. My own personal therapist has told me that I have major control issues. He says I like to highly control, organize, and curate every aspect of my life as a way to cope with a painful situation from my past that I had no control over. It’s part of why I like things in order, part of why I try to make things appear perfect, and part of why I have avoided meaningless relationships that might leave me vulnerable. He has challenged me numerous times to face this fear by completely letting go and relinquishing all control. I didn’t understand what that meant or how to go about it.

  In some strange way, this experiment ended up being the answer to this. We also discussed the importance of me putting less pressure on myself and learning to say “no” more often. When I take on too much, I become miserable, and both my work and my relationships suffer. We discussed how much happier I feel and how much my outlook and mood have changed since I’ve started taking better care of myself.

  Did you learn anything new about Timothy? Jocelyn discussed how Tim’s cycle of abandoning women likely goes back to being abandoned by his father. Jocelyn discussed how men will repeat this pattern in a way to identify with or feel closer to the absent parent. Over time, this pattern only makes the person feel emptier, as they never develop meaningful relationships.

  Did you learn anything new about yourself? We talked about how empowering it was for me to “let go” a few weeks ago and to stop trying to define the relationship. In the past I have put too much pressure on myself to determine if the person I was dating was right longterm. If a guy didn’t give himself to me wholeheartedly, I would give up on the relationship out of fear of failure. I couldn’t enjoy dating in the moment.

  How do you feel about this relationship/project right now? Tim mentioned how it would be a tremendous relief to date without the burden of recording everything every day. Amen!

  Is there anything that you want to do differently? I am looking forward to dating Tim outside of the experiment, but I don’t want to accidentally pressure him. There is no need to rush. I want to enjoy the journey, not get hung up on the destination.

  Additional comments? Disney World! Tomorrow!

  DAY THIRTY-SEVEN: APRIL 25, 2013

  Timothy Goodman

  Did you see Jessica today? Yep.

  What did y’all do together? Weekly therapy session. Last call!

  Did anything interesting happen? Jocelyn reinforced that I’m the “dominant” one in this relationship. I seem to be the one who’s in control, because I’ve been on the fence, while Jessie has been willing to dive in head first. I guess by default I am in control, but I don’t understand why Jessie can’t take some control. I’m not holding us for ransom, nor do I want to. I remember reading something a while ago about how relationships don’t fail because of little differences. They fail because of arguments about who is in charge and who is not in charge and the stress that comes along with that.

  We talked a lot about what Jessie and I have learned from the last thirty-seven days. We talked about what we’re going to do after Sunday. Admittedly, I’ve been trying to avoid thinking about this. Jocelyn asked me if I want to go back to dating other women. I have no interest in seeing other girls on day forty-one or thereafter, and I don’t want to stop seeing Jessie. I just want to see what happens when we’re outside of the parameters of this experiment. This hasn’t been “real” dating, and nothing about this experience has necessarily felt natural. While pressure can create diamonds, sometimes pressure can blow out from the bottom. I’m interested in seeing what could happen when we’re “unchained.”

  It makes me think of Dave, a former boss of mine I had right after high school. He eventually became an important mentor and a great friend. He has all these phrases he goes by, stuff like “Dress for the job you want, not the job you have,” and “Never put your hands in your pockets; it’s a sign of laziness.” Anyway, one phrase he says that particularly rings a bell in this case is, “Never say ‘I can’t.’” When will I stop saying “I can’t” when it comes to relationships?

  Did you learn anything new about Jessica? Jocelyn brought up how hard it is for me when Jessie gets down about things. That can have a major effect on your significant other, and it’s truly affected me throughout this experience. Jocelyn asked me to describe to Jessie what that feels like to me. Then Jocelyn mentioned to Jessie how valuable it is to hear something like this without the heat of an argument. She said it’s a significant piece of information for Jessie to know as she goes forth.

  Did you learn anything new about yourself? Jocelyn said I abandon women before they abandon me as a reaction to my missing father. This isn’t news to me, obviously, but when someone tells you that to your face it’s like a punch in the gut. I know it is a defense mechanism, a way to “get” them before they “get” me. I’m not proud of it.

  How do you feel about this relationship/project right now? I feel good about it. I feel like Jessie has been consistently chill the last two weeks, and I’ve been consistently allowing her into my life. I don’t feel the pressure from the gala anymore. I don’t feel pressure from her. I love this.

  Is there anything that you want to do differently? I want us to have the best possible time on our trip. I don’t want to worry about what’s happened in the past or what could happen in the future.

  Additional comments? I love making playlists for friends, and I love making playlists for trips. There is a real pleasure in
carefully and considerately selecting tracks that are appropriate for someone or something. (And I always need a reason to bust out Huey Lewis or a classic ’90s alternative song!) Obviously, I had to make a 40DD playlist for this Disney Trip! Forty songs that highlight every moment, smile, tear, or any other related experiences we’ve shared through this experiment.

  DAY THIRTY-EIGHT: APRIL 26, 2013

  Jessica Walsh

  Did you see Timothy today? Bright and early!

  What did y’all do together? I hailed a cab at 4:00 AM and picked up Tim at his apartment. We headed to JFK and arrived at Jet Blue’s terminal for our 6:00 AM flight to Orlando. I was very tired because I was unable to sleep during the night. I was too excited about the trip, and I stayed up making maps of the various rides we should go on.

  Did anything interesting happen? We boarded the plane and I fell fast asleep on Tim’s shoulder. I woke up as the plane was touching down. We took the Magic Express train to our hotel room at the Contemporary. We unpacked, had sex, and got changed into our bathing suits. We went to the pool bar and ordered a few mango margaritas. Tim scarfed down a disgusting looking hot dog as we strategized the plan for the weekend. We decided to tackle Epcot today, Magic Kingdom on Saturday, and end with Animal Kingdom on Sunday.

  We headed over to Epcot and ran around the park getting into all sorts of trouble. We went on the first ride, which was called “Mission: Space.” We were not prepared for it. Aren’t these rides supposed to be for kids?! We both stumbled out of the ride feeling dizzy with motion sickness, laughing at the hilarity of it all. We wandered over to the “Soarin’” ride after, which was a simulation of hang gliding over California landscapes with a wraparound IMAX screen.

  Tim became annoyed with me at several points in the day for various things, but I was able to brush it all off. There’s no need to fight around the children! We ended the evening with dinner at the Grand Floridian. I had asparagus and risotto, and Tim had the tomato and mozzarella.

  After that, we headed outside and watched the fireworks. I sat in his lap, and we sipped champagne. Things felt romantic. I realized how much I’ve let my guard down this past week. I am starting to admit to myself how much I care about him.

  After the fireworks, we lay in the grass outside our hotel and looked up at the stars. We noticed how clear the stars in the sky were compared to New York.

  We talked about the possibilities of alien life, string theory, and space travel. While I’ve always thought that 2013 is a great time to be alive in the history of the universe, I do wish we lived in a time where space travel was affordable for civilians.

  Lying under the stars reminded me of a friend who loves astrology and horoscopes. She recently suggested that we do a horoscope partner analysis together. I’ve never been a believer in the type of horoscopes you find in gossip magazines, but I have always been curious about them. I did some research, and I found a site with readings by a reputable astrologist whose work is based on Jungian psychology.

  Did you learn anything new about Timothy? Tim was born on June 23 at 9:19 PM in Ohio. He falls under the Cancer zodiac sign. Here is his personality portrait, and his psychological portrait.

  Did you learn anything new about yourself? I was born on October 30 at 10:05 AM in New York. I fall under the Scorpio zodiac sign. Here is my personality portrait, and my psychological portrait.

  How do you feel about this relationship/project right now? After we did our individual psychological portraits, we tried a relationship portrait together.

  Is there anything that you want to do differently? As I was reading these horoscopes, I became spooked by how the descriptions seemed to resemble our personalities, our issues, and even our pasts. Are these strategically written to make us all feel that we can relate? Do we just see what we want to in them? This makes me think of the idea of romantic fatalism. I often find myself looking for signs of fate in a relationship, like strange coincidences or similarities that make me think “it’s meant to be.” I can’t deny that I attach meaning to the coincidence that Tim and I are both die-hard Winnie-the-Pooh fans, or that we share the same favorite childhood ice cream flavor. But when you look for these signs between any two people, there are bound to be overlaps. I have to remind myself that the only meaning behind certain things is what we choose to attach to them.

  Additional comments? I had a good laugh at this part of the horoscope:

  DAY THIRTY-EIGHT: APRIL 26, 2013

  Timothy Goodman

  Did you see Jessica today? Oh yes.

  What did y’all do together? Disney World! Six AM flight JFK > ORL.

  I have a hard time sleeping on planes, but Jessie took a sleeping pill and passed out the entire time. When we got there we decided to do Epcot Center today. I remember crying the whole time I was there when I was kid. I thought it was so boring. Twenty years later, I don’t feel much different. However, the rides “Soarin’” and “Mission: Space” were awesome. Jessie was screaming at the top of her lungs during “Mission: Space.” I thought she was going to die.

  Did anything interesting happen? Later in the day we were sitting beside the pool and we started talking about her weight. How in the world I found myself in that conversation I haven’t a clue. But I know there’s no way to get out alive! She can be self-conscious about her weight, even though by general standards she is a stick figure. I stupidly told her that I’d love to see her gain about ten more pounds. This did not go over so well, obviously. I also realize that it’s not that easy for her to put on pounds. Again, I should have just shut my mouth!

  Did you learn anything new about Jessica? I was convinced that she had no interest in any bit of pop culture until today, when I found out that she LOVES Harry Potter. The things you learn about someone. Also, Jessie didn’t bring ANY high heels. I’m dumbfounded by this, too. Are we in bizarro world? But it was nice to see her in flats.

  Did you learn anything new about yourself? During dinner tonight we got into a conversation about her weight AGAIN. Damn, I really just need to shut the hell up. Here’s the thing: I LOVE to eat. I have no qualms about it. Highbrow to lowbrow, I’m in. I’ll eat sushi for lunch, and then I’ll kill a hot dog at the basketball game. And I like women who enjoy eating with me, especially when we’re on vacation or when we’re at an event. Plus, I’m six-foot-three, so it takes more for me to keep the tank full. She knows I like to eat, and I feel like she’s pressuring herself to eat more around me. It’s sweet, but I don’t want her to feel pressured into doing something she doesn’t feel comfortable with.

  How do you feel about this relationship/project right now? After the pool, we were in the sauna together. Jessie wanted to talk about what happens after day forty. She told me that I don’t need to feel pressured to date her after the forty days, which clearly means the exact opposite. The very mentioning of all this is indeed putting pressure on me. If we weren’t talking about any of this, then there would be no pressure. She said she understands if this relationship is not what I want and she’s cool if we just go back to being friends. Her mouth said it, but her eyes said the opposite.

  This worries me, because I know that what she’s saying isn’t true. Jessie is so black and white, and I know she needs to KNOW what the plan is for day forty. Can’t we just keep going and not talk about this stuff all the time? Everything has been so good lately. The questions and the pressure make me realize, yet again, that I don’t know what I want. And if I don’t know what I want yet, then maybe that’s enough to know that this isn’t right. I’m starting to feel a bit nervous.

  Is there anything that you want to do differently? At the end of the night we were watching fireworks from the Grand Floridian. They were beautiful. Children were running around, people were laughing, and we were cuddling. Something inside, however, didn’t feel right.

  Additional comments? There are two questions every person has to ask with any conflict or problem they need to solve: “How?” and “Why?” My old boss, Brian Collins, would
always say that “Why?” is a much more interesting question than “How?” As designers, we always want to solve problems—but instead, we should make problems by asking bigger questions of our clients and ourselves. Asking why encourages us to be provocative and memorable rather than simply making pretty things. As much as I strive to achieve that sentiment in my professional work, I think I understand what he means in a different context now.

  I can “solve” things with Jessie either by dating her or by simply walking away from this situation. But asking why I’m doing what I’m doing is a much more unpleasant, yet important, road to potentially go down. Essentially that’s what this entire experiment has been about: asking bigger questions and making a “problem” for ourselves when we could have just kept going with our regularly scheduled program. So am I willing to accept what may happen in the next two days? Am I brave enough to see what’s in front of me? And, if so, can I actually do anything about that?

  DAY THIRTY-NINE: APRIL 27, 2013

  Jessica Walsh

  Did you see Timothy today? Yes.

  What did y’all do together? It felt nice to wake up in Tim’s arms. We were out the door by 8:30 AM, on to Magic Kingdom. Tim scarfed down a cheese danish, a chocolate croissant, a microwaved egg sandwich, and a tea. This boy can seriously eat. After Tomorrow-land, we walked though Fantasyland and went on the the Winnie-the-Pooh ride.