Jessica Walsh
Did you see Timothy today? Yes.
What did y’all do together? We went to Easter brunch on the Upper East Side with Tim’s old teacher Sara from the School of Visual Arts. I was impressed by how sharp she is for an eighty-five-year-old lady. We talked about everything from the latest museum shows, to the TV show Girls, to politics.
Did anything interesting happen? Spending time with Sara reminded me of my grandfather who passed away years ago. Easter was one of his favorite holidays, and I couldn’t help but become nostalgic at brunch. I remembered how he’d give me a chocolate bunny every year. I’d only eat the ears.
One Saturday over five years ago, my grandfather was rushed to the hospital with heart problems. I spent the day with him, and when visiting hours were almost over, I couldn’t muster the courage to tell him how much I loved him. The next morning I missed the 8:05 train from Grand Central Station to Harrison, New York, by a matter of minutes. When I finally arrived, I knew from the look in my mom’s eyes that he was gone. He passed only ten minutes before I got there. I was devastated that I never got to tell him how much I loved him. My mom suggested that I handwrite him a letter. However, Poppy was proud that he learned to email just a few weeks earlier, so I emailed him my letter instead.
Poppy spoiled my grandma with love, attention, and so much food! He did everything for her. My mom always told us that we should never settle unless a guy treated us like this. I looked for this in relation ships when I was younger, but I always felt that it’s unattractive when a guy holds me too highly on a pedestal. When Poppy passed, my grandma didn’t know how to take care of herself. I think it’s good to find the right balance of mutual support, with the occasional spoiling on both ends, but I don’t want to ever depend on a guy.
Did you learn anything new about Timothy? Tim interacted with Sara with patience and kindness, which was nice to see! He told me about his own grandparents, and how close he is to them. It’s nice to hear that family is important to him, too.
Did you learn anything new about yourself? Poppy imparted so much wisdom to my family over the years. He was full of what my family would call “Poppyisms,” which were sayings that he’d repeat to us over and over and over and over.
How do you feel about this relationship/project right now? Like the last couple days, my headaches today were severe. I didn’t feel up for going to brunch, but it sounded important to Tim that I meet Sara, so I dragged myself there. It’s really hard to enjoy anything these days, I am in so much physical pain.
Is there anything that you want to do differently? Poppy always said that if you have your health, you have everything. I need to take care of this headache situation. Friday I have an appointment to go to a neurologist—maybe they will have better insight than my regular doctor. So it goes.
Additional comments? Tim was silent when Sara and I were discussing the most recent gallery and museum shows around New York. I’m only now realizing he doesn’t enjoy the art world as much as I do.
DAY TWELVE: MARCH 31, 2013
Timothy Goodman
Did you see Jessica today? Yessir.
What did y’all do together? We made plans to have Easter brunch with Sara, who’s a former typography teacher of mine. Sara is in her mid-eighties, and she’s always been really great to me. She’s as smart as a whip, and I appreciate her wisdom and knowledge. She was shocked when I told her that I’d be bringing Jessica along. It’s the first time I’ve ever introduced a girl to Sara.
Did you learn anything new about Jessica? After what happened last night, I figured Jessie wouldn’t come to brunch. However, she called me early in the AM to say that she still wanted to come. I was happy about that, but I was also a bit nervous. No need to bring our drama around someone over eighty.
When I picked Jessie up in a cab, I gave her one of those chocolate Easter eggs. I was trying to be funny and make light of what happened last night.
Did you learn anything new about Jessica? Sometimes Jessie doesn’t like to talk a lot. Sara was very excited to meet her, and she asked Jessie a lot of questions about her work. I know Jessie was super exhausted from the night before, and of course her headaches are horrible, but I don’t think she asked one question the whole time. But hey, the apple crumble was amazing.
Did you learn anything new about yourself? I brought Sara flowers. I think it’s important to be sweet and respectful to my elders, since I’ve always had a very close relationship with my grandparents. They’re both creative people, and their personal lives and their relationship have always been a big inspiration to me. They love to travel, and my grandmother still sends me postcards. The one on the left is from last September. She sent me the one on the right when I was eight years old.
How do you feel about this relationship/project right now? We didn’t really talk about what happened last night, and that’s fine by me. I feel like I’m walking on eggshells a bit. However, I gotta admit her Crazy is starting to turn me on.
Is there anything that you want to do differently? I can’t stress out when Jessie stresses out. I can’t let her mood swings bother me. We all have our problems, and I want to keep my cool no matter what happens.
Additional comments? Jessie looked cute at brunch. I like it when her hair is back.
DAY THIRTEEN: APRIL 1, 2013
Jessica Walsh
Did you see Timothy today? Yes. Almost naked, too.
What did y’all do together? We went to the Aire spa in TriBeCa. I’ve been several times with friends, and I love the hot baths and steam rooms. Tim bought me tickets to the Knicks game last week, his happy place, so I thought I’d treat him to one of mine. I got us the two-hour pass that includes a one-hour massage.
Did anything interesting happen? While we were in the steam room, Tim discussed why he didn’t think a romantic relationship between us would ever work. This meant ten minutes of listening to him point out all my quirks and weaknesses. If I didn’t know him so well, I would have either written him off or gotten offended. I’ve known Tim for years, though, and I know this is his normal routine when he likes a girl.
As soon as he starts seeing a girl, especially a girl he really likes, he’ll focus on bizarre things about her that bother him. These things are meaningless in terms of a relationship, but he claims they are deal breakers. A few months ago he dated a great girl who seemed to have it all, but he decided he should end things because he didn’t like her shoes. Seriously. The next girl he said he liked hooked up with him too soon. The next girl he dated was amazing but she didn’t like her career as much as he likes his. All of them are either too thin, too curvy, too quiet, too loud, not creative enough, not smart enough, have daddy issues, etc. The lists of these reasons go on and on.
There is no such thing as a perfect relationship. People aren’t perfect. No one likes perfection anyway, it’s boring. Tim knows this. I think he uses these excuses to protect himself from getting too attached to a girl. I think he fears that if he gets too close he’ll lose control of the situation and get hurt.
Did you learn anything new about Timothy? In the steam room I noticed he has a big tattoo sleeve on his upper arm. I don’t know how I missed this before. We talked about the meanings behind his tattoos and when he got them. He told me that one of his ex-girlfriends got a tattoo of his name. She wanted him to have her name tattooed on him as well, but they broke up before he went through with it.
Did you learn anything new about yourself? In middle school and early on in high school, I had serious struggles with perfectionism. I was terrified of breaking rules, I never had the guts to stand up for myself, and I had a massive fear of failure. I became shy and withdrawn, as I feared I might say something wrong. I hated my appearance, and I pushed myself too far at times.
Many years and many hours in therapy later, I’ve come to realize that the more I tried to reach perfection, the further I would get from it. I happily learned to embrace my quirks and weaknesses, and focus my energy on my strong suits. I am
far from perfect and I want to continue to learn and grow. However, I also want to be with someone who can accentuate my positives, not focus on my negatives.
How do you feel about this relationship/project right now? I have now admitted to Tim on a few occasions that I like him and I am curious to see if something more could develop between us. We still have to see each other every day for the next twenty-seven days, so if there was ever a time to try this out, why not now? Needless to say, he’s still confused and continues to send me mixed signals.
Is there anything that you want to do differently? I suppose I should listen to our therapist, who said I should be careful of how close I let myself get to Tim. He seems to be unable to admit to the idea that he likes me, so will he ever be ready for something more? Perhaps it is better we just stay friends.
Additional comments? My insomnia is now full-blown because of the headaches. I’ve been trying out various medications, and while they help me sleep, they make me extremely tired and foggy during the day. Thankfully my doctor’s appointment is tomorrow.
DAY THIRTEEN: APRIL 1, 2013
Timothy Goodman
Did you see Jessica today? Yep.
What did y’all do together? Jessie got us spa time and massages at Aire Ancient Baths. It was “payback” for the Knicks game. I couldn’t imagine a better payback!
Did anything interesting happen? While we were half-naked and sweating in saunas together, I brought up what happened Saturday night. She basically gave me an ultimatum: We either need to be just friends, or I have to tell her that I want more. Yes, I am interested in more, but it just feels too risky.
Did you learn anything new about Jessica? She looked all cute in her blue pants, beige sweater, and glasses. I feel like she wears black every day, so I was diggin’ the changeup. Secondly, I saw her with no shoes in the spa (she’s usually wearing heels) and I noticed that she walks pigeon-toed, which is super cute. Lastly, I like that Jessie can joke around about all this. I sent her an April Fool’s email this morning.
Did you learn anything new about yourself? Today I was chatting with one of Jessie’s close friends. She wants me to stop the project because of Jessie’s recent health issues. She said that Jessie “needs friends, not experiments.” It made me feel badly, because I want what’s best for Jessie, too! Jessie is a big girl, and if she wants out, then she’ll quit. She then asked me why I’m doing this project, what’s in it for me. I told her that I really believe it’s testing my capacity for intimacy. I haven’t emotionally let a woman in my life for a while, so opening up to Jessie and not having some kind of motive feels really nice.
How do you feel about this relationship/project right now? I’m concerned about our talk in the spa. What happens if we “go there” and then I don’t want anything else after the forty days? Won’t Jessie feel used? I’m not trying to “hit it and quit it.” I think a relationship with an expiration date is actually worse.
Is there anything that you want to do differently? Jessie was mildly talking about quitting the project or making it shorter. After the spa, I sent her a “BIG-ASS MESSAGE,” but she didn’t respond. I was just trying to be funny about the situation.
Additional comments? Everyone was teasing me Saturday night after Jessie left the dinner party. They said that I’m getting all the bad parts of a relationship without any of the good parts. Dammit.
DAY FOURTEEN: APRIL 2, 2013
Jessica Walsh
Did you see Timothy today? Briefly.
What did y’all do together? We grabbed a coffee at the Grey Dog, a cafe in Chelsea.
Did anything interesting happen? I finally got the official diagnosis from my doctor:
Lovely, right? I did feel somewhat relieved that the description at least touches on the absolute hell I’ve been experiencing the past few weeks.
I tried to talk to Tim about how this project is becoming an additional layer of stress in my life. I just can’t handle this while I’m experiencing my recent health issues. I asked him if we could just call the project “14 Days of Dating” and end it. He sort of laughed off my suggestions, pulled out his Moleskine, and had me fill out a PROS and CONS list about whether or not we should continue the project.
Did you learn anything new about Timothy? I didn’t realize until today how different our work situations are. He works for himself, and at the moment, his schedule is relaxed. I work with a team of people in a studio environment with a more consistent work flow. It’s very difficult for me to make time to see him every day.
Did you learn anything new about yourself? Tim and I talked about my “all or nothing” outlook in life and in relationships. I like to do things 100 percent or not at all. However, I know life isn’t always black and white, and whether I like it or not, this relationship is forcing me to accept shades of gray.
How do you feel about this relationship/project right now? I’m already overwhelmed and this relationship isn’t helping. Around lunchtime, we were chatting on instant messenger. I became busy with a client call, and I had to get some art files out to the printer. Our chat window became buried behind layers of documents, and I didn’t check it for a couple hours. When I did, I was greeted with this:
Is there anything that you want to do differently? I’ve read scientific studies that say if I pretend I’m in a good mood, or if I fake a smile, I can actually trick my brain into making me feel better. Well I tried it today, and I am sad to say that it does not work.
Additional comments? No, not today.
DAY FOURTEEN: APRIL 2, 2013
Timothy Goodman
Did you see Jessica today? Awkwardly, yes.
What did y’all do together? We met at Grey Dog for breakfast. Funny enough, we tried to meet here right after we first met four years ago. Evidently, she thought I was hitting on her back then—which I was actually NOT doing. I really liked Jessie when I met her, and I respected her work. I just wanted to get to know her better.
Did anything interesting happen? We talked about our “relationship,” but everything about our conversation felt so heavy. It was full of innuendos and cryptic bullshit. I felt like we just needed to be more honest with each other. I took out my notebook, ripped out a couple sheets of paper, and suggested that we write “pros” and “cons” about this project/relationship. It’s always easier to be honest on paper, but I don’t think this really changed anything.
Did you learn anything new about Jessica? She’s always too busy, too stressed, and ultimately too serious these days. I know the headaches are getting worse, and now she has insomnia, too. I feel really bad for her—and on top of it all, she’s under a lot of pressure at work. When I worked at Apple, I would rush home to do freelance work until 2:00 AM every night. I was always putting pressure on myself. Jessie does the same thing. She’ll do whatever it takes to be in control, and she certainly doesn’t like it when someone worries about her. She reminds me of my mother that way. My mom would lie to us about her health if it meant no one would worry about her.
Did you learn anything new about yourself? I feel a lot of pressure from Jessie. I like a bit of uncertainty, and I like living in the questions. I don’t like having to live up to some idea or to fulfill some expectation, though. I don’t think she even realizes she’s doing it. The whole situation is making me feel very unsettled, and she wonders why I’m being so wishy-washy.
How do you feel about this relationship/project right now? After two weeks, I feel much closer to her, much more intimate, and I’m attracted to her. On many levels, I am enjoying this. However, because of what’s going on with her, I do feel vulnerable. When I got back to the studio, I saw this movie trailer with a voiceover that said, “To commit yourself is to run the risk of betrayal, the risk of failure.” Seriously, Universe?
Is there anything that you want to do differently? I just want us to find some sort of normalcy. We’ve been overanalyzing everything and getting way too serious about stuff lately. The parameters of this experiment seem to be ba
cklashing on us. If this is what it’s going to be until the end, then kill me right now.
Additional comments? It never struck me until today, but Jessie sorta has an Eddie Murphy laugh! (In a cute girl-way, of course.)
DAY FIFTEEN: APRIL 3, 2013
Jessica Walsh
Did you see Timothy today? No.
What did y’all do together? We spoke on the phone.
Did anything interesting happen? I had dinner last night at Roberta’s Pizza with a few girlfriends. Afterward, I shared a cab ride home with one of my closest friends. We talked about this project and my health. I broke down crying. I told her how overwhelming everything has become with my headaches and insomnia. I’ve been researching treatment solutions for the headaches, and the options are not good. The pills they’ve given me are extremely addictive and they cause rebound headaches. Surgery or anesthetics could be a possibility, but sound risky. The idea of living a lifetime in this pain is depressing.
My friend told me that she asked Tim several days ago to end the project because she was so worried about me. The more time I spend with Tim, the more I really care about him. Learning this made me wonder if Tim might care more about this project than he does about my well-being.
Did you learn anything new about Timothy? One of the girls I was at dinner with admitted to sleeping with Tim many years ago. This is the third time this week that I’ve learned he’s been with someone I know.
Did you learn anything new about yourself? Growing up, my parents put a huge emphasis on perseverance. One of my most vivid memories was when I desperately wanted to quit Tae Kwon Do training after receiving a yellow belt. I just had way too much going on with school and other sports. They convinced me to stick with it, and I was grateful. Receiving that black belt felt unbelievably rewarding.
40 Days of Dating: An Experiment Page 7