40 Days of Dating: An Experiment

by Jessica Walsh

  Did anything interesting happen? At one point in the afternoon I decided to use paint to cover our arms and legs, which we photographed as source material to create typography. The moment I finished painting myself blue, the elevator doors opened and Tim entered the studio space. I was pretty embarrassed! However, after four years of friendship, he already knows that I can be pretty strange.

  Did you learn anything new about Timothy? Tim brought BJ, a sixteen-year-old kid he mentors through Big Brothers Big Sisters. I found it very sweet that he is a part of BJ’s life. I know Tim has amazing mentors who have been an important part of his personal and professional development. It’s great he is in a place where he can do the same for others.

  Did you learn anything new about yourself? Usually I am an overplanner when it comes to photo shoots like these. But reflecting on past work, often the best results came when I wasn’t trying so hard. They came out of periods of spontaneity, play, boredom, or even mistakes. So today was about just getting off the computer and just making shit. There was definitely a fear of failure, but we produced some unexpected and interesting things.

  This makes me realize that I too often rely on working with a plan. I operate off of to-do lists. I can’t even remember a meeting or dinner date if it is not in my iCal. These apps have become a second brain and they’re starting to run (and arguably ruin) my life. Even romance has become overly planned these days. Almost every single friend of mine has used online dating to find their partners, including myself. These websites collect your data, analyze it, assign you numbers through arguably arbitrary algorithms, and give you an ordered list of likely lovers. They tell you percentage-wise how much of a match they are, even how likely the person is to respond. We no longer search for romantic partners, we shop for them. Just like when looking online for a new pair of shoes, one can sort men by highest rated, size, popularity, even by color. While I admit it’s all very practical, I have to wonder if it’s caused me to miss out on spontaneous interactions or chance encounters. I don’t even think to look around for guys in the real world anymore!

  How do you feel about this relationship/project right now? As I’ve been thinking about risks today, I keep coming back to something Jocelyn said in therapy. She thinks that in a way this project is cowardly. She asked why not just take the risk and just try to actually date, like the rest of the world. I think she senses there is interest on both ends, and she’s trying to push us together.

  Is there anything that you want to do differently? Risk failure in my life more often.

  Additional comments? The photo shoot is over, and I haven’t slept in forty hours. I might crash from exhaustion soon...

  DAY NINE: MARCH 28, 2013

  Timothy Goodman

  Did you see Jessica today? Yes.

  What did y’all do together? Jessie was doing a twenty-four-hour event/installation for Adobe at Go Studios on 29th Street. I stopped by the space around 6:30 PM to say hello and hang out for a little bit. I brought my buddy BJ, who is a young man that I’ve been mentoring for the last four-and-a-half years through Big Brothers Big Sisters. I thought he would like to see the fun Jessie and her studio can have with creativity.

  Did anything interesting happen? We hung out, ate, and watched Jessie and her studio mates cover themselves in body paint. After an hour, BJ and I left to go see a movie.

  Did you learn anything new about Jessica? I was thinking about our therapy session yesterday, and how badly Jessie wants to be in love. I don’t understand what she’s worried about. She’s a great catch: talented, smart, honest, attractive, humble, and successful. Last year I created a project where I attempted to draw a unique valentine for every single one of my Twitter followers on Valentine’s Day. It’s funny to think about the card I made for her.

  Did you learn anything new about yourself? I like to flirt, and it really hit me tonight that my flirting can’t be used as a tool for anything more right now. Not exactly groundbreaking, but it’s been a while since I had to filter myself. This is probably a good thing because I don’t want to be the old guy in the club one day thinking that my flirting is cute when, in fact, it’s just creepy.

  How do you feel about this relationship/project right now? I feel good. It was nice to see her today. I don’t know why I thought of this, but I noticed that we’re both punctual people. As much as I don’t love all her overzealous planning, I do appreciate that aspect. I feel like 90 percent of the girls I date are constantly late.

  Is there anything that you want to do differently? Nope, I think I was perfect today.

  Additional comments? BJ is seventeen now, and I like to bring him around my work life sometimes, so he understands all the opportunities that are possible. As a teenager I was in constant search for an identity, always looking to fill the shoes of my missing father. I soon found an array of mentors in my life that I copied character traits from. They couldn’t teach me how to shave, as a father might have, but they gave me the tools to gain confidence in my life. And it’s no surprise that my relationship issues come from the same place, but perhaps a level of sincerity and a search will help that, too.

  DAY TEN: MARCH 29, 2013

  Jessica Walsh

  Did you see Timothy today? Yes.

  What did y’all do together? Tim suggested forced me to go to a Knicks game at Madison Square Garden. I would never go to a basketball game on my own. Considering I haven’t slept in days due to the Adobe shoot, I can’t really say I was super excited about going. At least Tim was!

  Perhaps it helped that I had very low expectations, but it turned out to be a really fun evening! I loved the food vendors and all the people-watching. We ended up talking through most of the game, which was fun. I also couldn’t help but smile seeing how giddy Tim was about being at the game. It was really quite cute.

  Did anything interesting happen? I ate sushi at a Knicks game. Yes, I went there, and it was pretty awesome. After the sushi, I was craving something sweet. I suggested that we split bread pudding from Magnolia Bakery, which is one of my favorites.

  Did you learn anything new about Timothy? He is not very good at sharing. As we were paying for the bread pudding, he decided he wanted it all to himself and told me I should get my own! I didn’t think I could finish a whole bread pudding, so I bought a cupcake instead.

  Did you learn anything new about yourself? I used to love sports, and I had an extremely active childhood. I played varsity soccer and lacrosse. I spent summers hopping from one fitness boot camp to the next. I trained privately for eight years in Tae Kwon Do. I did hundred-mile cycling trips, ran track, played tennis, golf, and even basketball. Then I went to art school. Sports were a joke at my school. Our basketball team was called “The Balls.” The swimming team was “The Wet Dreams.” The hockey team was called “The Nads.” (You’d cheer “Go Nads!”) Needless to say, I phased out of my sporty past, and in the past few years I’ve had no exercise. Lately I’ve been dealing with terrible headaches, back pain, and feeling sluggish all the time. Tim keeps nagging me to try exercising, and I do wonder if setting aside time for physical activity might be helpful.

  How do you feel about this relationship/project right now? I could sense Tim being a little flirtatious during the cab ride home, but something was holding him back. I suppose it goes back to what we discussed in our therapy session. He’s interested, but he’s afraid to take the risk since he doesn’t know what he wants. I think he’s overthinking things.

  Is there anything that you want to do differently? It was nice to get out of my comfort zone and try something new. I want to diversify my interests, as there are so many interesting things to do in NYC! Salsa dancing classes, anyone? Rock climbing? Mixology classes? Kickboxing?

  Additional comments? The game tonight reminded me of my parents’ relationship. They always said you need a “give and take” attitude in a long-lasting relationship. They are both business people, and early on in their marriage they developed a credits-and-debits “point system�
�� to keep things in balance. Here’s an example:

  Going to the Knicks game tonight would have totally earned me at least twenty points. I’ve already started plotting my revenge date. Gotta keep the T&J score in balance.

  DAY TEN: MARCH 29, 2013

  Timothy Goodman

  Did you see Jessica today? Word.

  What did y’all do together? I took Jessie to her FIRST Knicks game. I mean, she’s never been to the “The World’s Most Famous Arena”!? Needless to say, I was excited. I love going to NBA games (this is my third game this month). Nothing is further away from the design community, nothing relaxes me and lets me escape more.

  Did anything interesting happen? We talked a lot during the game. Luckily, the Knicks were destroying the Bobcats, so all this talking was totally fine.

  Did you learn anything new about Jessica? She bought sushi at a Knicks game. Really? I, on the other hand, ate a huge hot dog and a pile of bread pudding. I was proud that she ate a cupcake in the third quarter, though! Also, I noticed that Jessie and I rarely talk about design, which is refreshing.

  Did you learn anything new about yourself? I have an affinity for NBA basketball because it reminds me of watching the Cleveland Cavs with my grandfather when I was a young boy. I think there’s a bond that two people form together while watching a game among twenty thousand people.

  How do you feel about this relationship/project right now? We’re one-quarter of the way through this project, and I thought that seeing each other every day would be more difficult. I’m fine right now, but I can still feel that she is uncertain.

  Is there anything that you want to do differently? I wanted to invite her back to my place, but I was unsure of my intentions. So I didn’t. I don’t want to lead her on. This is getting tricky.

  Additional comments? It was still early in the night when the game ended, so I went down to Whole Foods to take care of some food shopping. I was thinking about the times I’ve actually met women in Whole Foods. (In the last six years, I’ve gone out with four women in six attempts.) The experience there is one that’s designed for consumers to feel completely comfortable and friendly: the dark mahogany woods, the cool choice of music, the scents, the utilization of several floors, having a place to eat, and of course the organic food. It slows you down, almost to the point where you want to be there.

  Now, you’d think a grocery store is a horrible place to meet a woman, right? They’re focused on shopping, and the last thing they want is some guy hitting on them. Women are much more open to meeting someone if they’re comfortable, though. The more comfortable women are, the less of a rush they’re in, the more friendly they become. Whole Foods maximizes this collective effort of comfortability better than any of their competitors. Trust me, no one is friendly in a Safeway. The problem is that most guys don’t know how to meet women outside bars, their workplace, or OkCupid. Meeting a woman in a public place can be difficult, and the guys who do hit on women in public places are usually creepers. However, women are undoubtedly impressed with a confident and spontaneous guy who has the courage to spark up a conversation in an atypical place like Whole Foods. It’s much more exciting to meet someone when it’s spontaneous. Men, you should learn how to create serendipity.

  DAY ELEVEN: MARCH 30, 2013

  Jessica Walsh

  Did you see Timothy today? Sigh.

  What did y’all do together? Our friends Lotta and Jonathan were hosting an Easter potluck dinner with “the family.” That’s the nickname I gave our group of friends. We joke that I’m “Grandma,” since I’ve been known to go to bed super early. Tim named himself the “Slutty Sister.”

  Did anything interesting happen? Earlier today, I went to see the NYC 1993 show at the New Museum and the Gutai show at the Guggenheim. Gutai was a Japanese artist group led by Yoshihara Jirō. They did a large body of experimental work together in the fifties and sixties including paintings, installations, exhibitions, and films.

  After the shows, my mind was racing with new ideas that Tim and I could collaborate on. I wanted to share a little of this inspiration with him, so I picked up several books for him at the museum gift shop. I thought it would be a nice “thank you” after the sweet video he made me the other day.

  I gave him the books on the cab ride to Brooklyn and started to tell him some of my ideas. As he opened the gifts he became irritated and tried to pick a fight. Not the reaction I was hoping for! He said my fluctuating mood was stressful. I was a little tense leading up to my big photo shoot the other day but have since been upbeat and happy. His own moods fluctuate quite a bit, too. Yesterday he was happy, today he’s crabby. Anyway, I was able to calm things down, but it definitely killed my mood. At least the dinner was wonderful! We feasted on asparagus pie, ravioli, and lemon cocktails.

  Right after we finished eating, a few things happened in succession. First, a wave of exhaustion hit me. I didn’t sleep at all the night of the Adobe shoot, and I only slept a few hours per night for the rest of the week. Secondly, I’ve been getting these terrible headaches lately, and it became unbearable after dinner. Next, I started to mull on Tim’s reaction to the gifts from earlier in the evening. And lastly, I got a text message from that ex who broke my heart last year:

  My heart sank. I thought I was over him, but I guess I’ve been holding on to hope. All I wanted to do was go home and crawl under my covers. Everyone was having such a great time, and I didn’t want to kill the mood. I pulled Lotta aside and let her know what was going on, and then I left.

  Did you learn anything new about Timothy? Tim can be grumpy and moody. I don’t hold it against him, though. We can all get that way.

  Did you learn anything new about yourself? I stress because I give a fuck. Whether it’s in my work or my relationships, I’m very passionate. When I care about someone, I tend to care and empathize with them very deeply. Tim is starting to enter this “I care about you” zone, so I internalized his crabby mood. I let it get to me.

  How do you feel about this relationship/project right now? Later that night, I decided to call Tim and tried to talk to him directly about what he was feeling. He’s been overthinking everything and sending me mixed signals. He’s both interested and scared to become intimate, yet he’s still being flirtatious and showing signs of wanting more. Why is this so difficult? The back and forth is confusing, and I’m tired of playing guessing games about what he wants. He said he had had a few too many cocktails, and that he’d prefer to talk about everything in the morning.

  Is there anything that you want to do differently? I shouldn’t internalize the moods of the person I am with so deeply, it’s been a source of stress in my past relationships.

  Additional comments? All our friends at the dinner party were couples. I watched as they exchanged kisses, teased each other, laughed with each other, etc. I can’t deny that I felt a little envious.

  DAY ELEVEN: MARCH 30, 2013

  Timothy Goodman

  Did you see Jessica today? Oh boy.

  What did y’all do together? Our friends Lotta and Jonathan invited us over to their place for an “Easter Feaster” dinner party with some other friends of ours, three other couples.

  Did anything interesting happen? Jessie and I shared a cab on the way over there. I was already in a crabby mood from my day, and I ended up picking a fight with her. The last couple days she’s been stressed, and when this happens, I can really feel that energy. This can be frustrating for me, so I think I took it out on her. Anyway, Jessie was in a great mood and she was inspired from museum hopping all day. She even brought me a bag of gifts. It was very sweet. I’m sorry I was being an asshole.

  After the cab ride, I figured it couldn’t get worse. Well, it did. Things were great until dinner, when everybody started asking us about the project. Jessie seemed uncomfortable talking about it, and she became very aloof. She eventually left without much explanation to anyone. Now, I’m at the dinner party feeling like the bad guy, and everyone is asking me why she left
. D-R-A-M-A.

  Thirty minutes later, she called me to say that we needed to “stop playing games.” What does that even mean? I’m not playing games, I’m being cautious! As I keep reiterating, I’m not interested in leading her on or hurting her. Can’t we just hang out, be cool, and see what happens naturally? I told her that we should discuss this tomorrow, since we had both had too much rum cocktail.

  Did you learn anything new about Jessica? Lately, I feel like her mood can sway at any given moment. I know she’s stressed from her headaches—and my uncertainty is not helping—but her moods are draining me.

  Did you learn anything new about yourself? She made a comment at dinner, jokingly saying I’m “controlling.” I know I was a jerk in the cab, but now I’m controlling? It didn’t make me feel so good.

  How do you feel about this relationship/project right now? Not good. She seems very affected by this project. She wants more from me, and I feel pressured about it.

  Is there anything that you want to do differently? Everything.

  Additional comments? All I could think about was that line from The Real World, “When people stop being polite and start getting real.” Yup, here we go.

  DAY TWELVE: MARCH 31, 2013