First dates are the perfect time to be spontaneous. After a couple months she was disappointed that I was working so much. Besides, I can’t always be exciting.
She was literary and liberal, it was late, I had too much to drink, and I thought it would be a good idea to read out loud.
It’s nice to have someone to lean on when things get lonely. She and I did that for years after college without any sort of question, conflict, or expectation.
She had the beauty, the essence, the attitude, the passion, the complexity, and the dark features. But I was moving to San Francisco at the time and it wasn’t going to work.
She had an amazing TriBeCa loft, and she’d even steam my shirts in the morning.
I guess it’s easy to romanticize the past, but sometimes it’s impossible to know how important someone is until it’s too late. If I had to do it all over, there are two or three girls I’d try again with.
She photographed me for a design magazine I was featured in. We had a great connection, but she wasn’t over her ex-boyfriend, and I wasn’t being serious enough.
We drove the Pacific Coast Highway from Los Angeles to San Francisco, blasting Tom Petty the whole way, stopping in Big Sur to take in the awesomeness.
We’ve all been on both sides of the coin. I can only think of the Bob Dylan line, “I didn’t mean to make you so sad, you just happened to be there.”
How do you feel about this relationship/project right now? Jessie has always been in the “friend-zone” to me, because I wouldn’t want to screw up our friendship. But I must say that I was really enjoying her company today. I started thinking about possibilities.
Is there anything that you want to do differently? Do I really like all this dating or is it just my ego? Do I really want to settle down or is that just pressure from society? Either way, I want to slow it down. I do miss having that one person you can connect with.
Additional comments? I left Jessie’s that night and met up with my good friend and his boyfriend. As the three of us ate dinner, I observed how much consideration and respect they had for each other. They were happy. After spending a whole day analyzing my past relationships, I couldn’t help but want that, too.
DAY SIX: MARCH 25, 2013
Jessica Walsh
Did you see Timothy today? Yes.
What did y’all do together? We went to the Ace Hotel for drinks with a few mutual friends.
Did anything interesting happen? I heard negative feedback from a few friends and colleagues about this experiment. They all want to know if Tim and I are “really dating.” They don’t believe that it can be a real relationship if we are not physically intimate. They think it’s a necessary part of the project. While I disagree, all the talk about sex and relationships did pique my curiosity as to what Tim’s interests in me are. Beyond admitting that he found me attractive in therapy, I haven’t sensed any desire from him to push it further.
I know from past experiences that I can be blind to these types of things. If a guy is interested in me, why can’t he just be straightforward about it?! I hate trying to interpret ambiguous messages and signals. I’m too old and too busy to play these dating games.
Tim must have been able to tell something was on my mind as he asked what was wrong. I shared some of the criticism I heard earlier. I told him I thought it would be fine if we did the entire experiment just as friends but was open to possibilities. In retrospect, it was not the most opportune time to discuss this, since we had already had a few cocktails. Tim became defensive and argumentative. I think he felt pressured. I tried to talk him down and calm things down, but it felt as if he was misconstruing every word. Before we knew it, we were in our first fight.
I’ve read that the source of most misunderstandings is that we judge others by their actions and ourselves by our intentions. I am sure Tim thought I was looking for answers, but I just wanted to talk things through. I’m just sorry I couldn’t explain myself more clearly tonight.
Did you learn anything new about Timothy? Tim seems to enjoy conflict on some level.
Did you learn anything new about yourself? I hate conflict and avoid it at all costs. Probably to a fault.
How do you feel about this relationship/project right now? After all this questioning about whether or not we are in a “real” relationship, I decided to look up the official definition. Gotta love Urban Dictionary.
Is there anything that you want to do differently? I can’t let other people’s opinions bother me if I want to make it through these forty days. I need to go with my gut—it has always served me well in the past.
Additional comments? Stefan (my business partner) left this on my desk. Hoping tomorrow will be better.
DAY SIX: MARCH 25, 2013
Timothy Goodman
Did you see Jessica today? Yes.
What did y’all do together? I had to be at the Art Directors Club for a Young Guns meeting tonight, and we planned to meet up afterwards at the Ace Hotel with our mutual friends Michael and Dan.
Did anything interesting happen? Michael and Dan left after a quick drink, so we stayed for another one with my friend Rich. I could feel some uneasy energy coming from her, so I asked her about it. Apparently some of her friends think this project is fake because we’re not in a “real relationship.” They all want to know if we are doing this project as friends, or if we’re doing it as a couple. Jessie was clearly bothered by it. It’s obviously something that she’d been thinking about as well.
I felt pressured to give her an answer, and we began to bicker about it. I don’t want to fulfill some idea that her friends have. That’s not what this project is about. We already are friends, so why do we need to define it any further right now? I can’t just say “Voila!” and be in a relationship.
We left the Ace in a bit of a tiff. I walked her to a cab, and we gave each other a half-assed hug. Things felt super weird. It was the first time Rich had heard about this project, so he asked us a ton of questions about it. Then he was contemplating whether or not we should be having sex, which made things a bit awkward. Anyway, he sent this old movie trailer to us afterwards. I can’t stand Jeff Bridges, but this is hilarious in context.
Did you learn anything new about Jessica? She likes to define everything. She likes to doubt everything. I think she listens to her friends too much. This is an experiment—and you can’t really define an experiment until it’s finished, right? It’s like getting a brief from a client; a client gives you the parameters, and it’s up to you to play.
Did you learn anything new about yourself? Her doubts make me doubt, which makes me anxious. I just want to have fun. I don’t need to define it all. Truth is, I probably could date Jessie in “real life” if I didn’t already know too much. I know how quickly she falls for guys, how fast she wants things to go. I have commitment issues as it is, so this scares me. I need to drive slow.
How do you feel about this relationship/project right now? It’s fine, I just don’t feel great about it right this second.
Is there anything that you want to do differently? I felt pressured tonight, but I need to react differently.
Additional comments? Bad night, but at least we made some fun memories in the Ace Hotel photo booth!
DAY SEVEN: MARCH 26, 2013
Jessica Walsh
Did you see Timothy today? Yes.
What did y’all do together? Tim met me at the Art Directors Club gallery in Chelsea for the SVA student show. A few of my students had work displayed in the exhibition, so I wanted to be there to show my support.
Did anything interesting happen? My fellow teacher Kevin O’Callahan asked his 3D design students to redesign gumball machines based on a theme of their choice. When I put a quarter in, I received a capsule with something unique inside relating to their theme. The machine I was most excited about was themed “Curiosity.” Inside the capsules were anonymous secrets from SVA students. I entered quarters and received two capsules for Tim and myself. It was almost to
o good. We had to laugh at the irony!
Here was the secret I received:
Here was the secret Tim received:
Did you learn anything new about Timothy? Later in the evening Tim sent me a bunch of text messages asking me if I had met any hot guys after he left. I was kind of confused by them—was he jealous?! I had an ex-boyfriend who was extremely jealous and it drove me nuts. Why date someone if you don’t trust them?
Did you learn anything new about yourself? My secret message made me think. This past year of dating has been tiring. The guy I was crazy for lost interest in me, and I wasn’t as interested in the ones crazy for me. Why does it always seem to go that way? I researched it tonight, and there is quite a bit of science behind why we are so attracted to what we feel like we can’t have. It’s called “The Scarcity Principle.” I guess this is how Tim gets all those girls!
According to this principle, if I want to attract guys, I should make myself scarce, play hard to get, and pretend I am not interested. This seems tiring! I’m hoping that if the right guy comes along, this won’t be necessary.
How do you feel about this relationship/project right now? Tim and I exchanged a few emails this morning after our disagreement. I am feeling better about it all!
Is there anything that you want to do differently? Today made me think about the topic of secrets. I had kept a few very personal things to myself throughout my life, but getting them out lately via therapy has been a huge weight off my shoulders. I want to be more open. Keep no secrets.
Additional comments? I don’t care how bad it is for you, MSG delivered straight to my door makes me happy. Nom nom nom.
DAY SEVEN: MARCH 26, 2013
Timothy Goodman
Did you see Jessica today? Yeah.
What did y’all do together? I met her at the Art Directors Club SVA student show. Yes, it’s the second day in a row I’ve been there—but we both teach at SVA, and I like to support our chairman, Richard Wilde.
Did anything interesting happen? We walked around the gallery and admired all the fun 3D projects. One of them asked students to transform or reimagine gumball machines in an unexpected and memorable way. My favorite concept was a machine that said, “Are You Curious?” For every quarter we put in, we got back a random handwritten secret in a capsule.
Well, Jessie put a quarter in and got back a note that said something like, “I worry that I will never find love.” We had a nice laugh about it, but I could see that it bothered her, that a part of her really feels this way. When I put a quarter in, I got back a note that said, “I take pictures of all my panties.” Ha! Now that’s my kind of a note.
Did you learn anything new about Jessica? Later that night, I tried to flirt with Jessie a bit via text message. I enjoy flirting and being playful, but Jessie either takes me a bit too literally, or she just doesn’t like to play back.
Did you learn anything new about yourself? When I was younger, I’d get really hung up on little arguments like we had last night. I’d dwell on them. I’m no longer like this, thank goodness.
How do you feel about this relationship/project right now? Much better than I did yesterday! We talked during the day, and we said our “sorries.” Although we did get into this discussion over email this morning.
Is there anything that you want to do differently? I couldn’t wait to get out of the Art Directors Club. I just need my own space after the last couple days. But I want to confront this energy because we still have a long way to go.
Additional comments? Seriously, the word “panties” has to rank among the top ten words. I even did some research on the word because I liked it so much. I’m not going to share said research, though. Some things are better left unaddressed.
DAY EIGHT: MARCH 27, 2013
Jessica Walsh
Did you see Timothy today? Yes.
What did y’all do together? We went to our second therapy session together. I felt bombarded with questions from the therapist. Although these question sessions are highly uncomfortable, they do push us to unexpected places.
Did anything interesting happen? I’m an overly curious person who questions everything from the workings of the universe to what’s in my morning latte. I like to keep questioning, it keeps me learning. However I know I can take it too far and overanalyze things. When I can’t figure something out, it can drive me a little crazy!
Since our disagreement at the Ace Hotel the other night, I’ve been overanalyzing the situation. Does Tim have an interest in me romantically? If he does, will he make a move, or will I? Why is it so hard for him to figure out what he wants? Is he really what I want? Why am I becoming insecure? Is this project crazy? Is this project making me crazy?
Our therapist asked Tim about whether he wanted an intimate relationship with me, which spared me having to ask the question. He admitted he was interested, but that he was confused about what he wants. He became anxious, he hates any kind of pressure. I may have to accept that I won’t figure this one out anytime soon.
Did you learn anything new about Timothy? Truthfully, I didn’t want to go to therapy today. I had a terrible headache and I am overwhelmed with work. The therapy session was emotionally draining, and afterwards I was feeling really down. Tim must have recognized this, as I came home after work to find this video in my inbox. It was super cute and reminded me how perceptive he can be.
Did you learn anything new about yourself? In therapy we discussed my family dynamic. Both my parents and my grandparents married in their early twenties and had long, loving, happy relationships. The therapist talked about how this can unconsciously create pressure.
When I was younger, I did imagine following my family’s path. I really thought it was just like The Game of Life: I’d go to college, meet a nice boy there, get married to him in my twenties, and have kids by the time I was thirty. However, I moved to New York, where it’s not as common for people to get married or have children in their twenties. I’m completely dedicated to my work right now, so I’m not sure what I want anymore.
How do you feel about this relationship/project right now? I can’t deny that it’s been stressing me out a bit, but Tim’s video lifted my mood.
Is there anything that you want to do differently? I talked about the future with my own therapist, and why I feel any sense of urgency or pressure. My therapist says it’s because I am a problem solver at heart. I am the kind of person who likes to figure things out, and I like things settled. I’m happy in most other aspects of my life, but romantic relationships is the one area that’s been up in the air. He said I should accept the mystery of it all, and just enjoy the journey.
Additional comments? Still a big grin on my face from the video Tim made me.
DAY EIGHT: MARCH 27, 2013
Timothy Goodman
Did you see Jessica today? Yes.
What did y’all do together? We had our second appointment with our therapist.
Did anything interesting happen? I feel like Jocelyn was less intense with the questions this time. Jessie and I talked about our families, and how our own relationships have been affected by our parents’ relationships. We come from different family backgrounds, so we tend to think about things differently. I never met my biological father, and I grew up with two different stepfathers. Jessie’s parents are still happily together.
Jocelyn said we need to use our time with her as a “safe place” to talk about things openly. I was much more open discussing things today than Jessie, who seemed distant and removed. I know she’s very tired from dealing with a lot of stress at work. This project seems to only add another layer of stress to her life these days. I felt bad, so after therapy I went home and made her a little video.
Did you learn anything new about Jessica? Jocelyn said this project is good for Jessie. She said that Jessie dislikes the discomfort or awkwardness in the beginning of a relationship, which is why she gets serious so fast. I guess I knew this, but the way the therapist described it really made m
e have an “aha moment.”
Did you learn anything new about yourself? We talked about the boundaries I put up in the different relationships in my life. I am good at being a friend, and I’m good at jumping in and out of a woman’s life, but the emotional intimacy is where I’ve gone astray lately.
How do you feel about this relationship/project right now? I’m totally fine with what’s going on between us, but I don’t think Jessie is. I can tell she wants more from me, even if she doesn’t say so.
Is there anything that you want to do differently? The therapist asked me to try to give more intimacy to Jessie. I’m going to try. We just gotta keep on pushing!
Additional comments? After therapy, I was thinking about my childhood. I was a scrappy kid, always looking for the thrill of doing something “bad.” When I was ten years old, I started stealing my stepfather’s cigarettes and his old copies of Playboy. I would run into the garage and look at them with my friends in astonishment. It felt risky and grown-up. My favorite was the March 1989 issue with La Toya Jackson on the cover. I was a huge Michael Jackson fan as a kid and I found the La Toya issue to be so completely fascinating and dirty. Why would his sister pose nude for the whole world to see? Isn’t that embarrassing for Michael? And moreover, why was I so turned on by this?
DAY NINE: MARCH 28, 2013
Jessica Walsh
Did you see Timothy today? Yes.
What did y’all do together? I was working at Go Studios in Chelsea. Our studio was doing a creative session for Adobe for their new Creative Cloud branding. The photo shoot involved locking ourselves in a photo studio for twenty-four hours straight to “play” and see what we could make. I wasn’t allowed to leave the studio space, so Tim came to visit me.
40 Days of Dating: An Experiment Page 5