Day Forty   /   lettering by Dana Tanamachi

Jessica Walsh

Did you see Timothy today?

What did y’all do together?
We spent the morning running around to the various rides. We didn’t speak about last night’s events. The constant noise and visuals at Disney’s Animal Kingdom proved to be the perfect distraction from the disappointment and pain.


Did anything interesting happen?
Around noon we sat down at an outdoor bar and drank margaritas. After we ate, I began to feel quite faint. The combination of the sun, alcohol, and exhaustion from the walking must have dehydrated me. Tim helped carry me out of the park. Around 5:30 we took the Magical Express back to the airport. We schlepped our bags through security, and we ate dinner at the bar of some Mexican restaurant in silence. Tim watched the basketball game while I read my book.

Tim finally broke the silence, and suggested we address the elephant in the room. I asked him if his feelings had changed since last night, or if he wanted to try to make it work. He said he still didn’t feel it was right between us. I told him that as deeply as I care for him, he deserves to be with someone he is crazy for, and I deserve to be with someone who is crazy for me. He agreed, and he said it would be better to end things now before he could screw things up even more. We boarded the plane, and I cuddled up in the window seat with a blanket and pillow. I listened to Lana Del Rey’s Born To Die on repeat, which helped me through my last breakup. I downed a few miniature bottles of red wine to drown my sadness, and I finished the last chapter of my book.

Did you learn anything new about Timothy?
What does it even mean to love someone? It seems almost impossible to universally define such a complex state of mind since we all experience life so uniquely. I guess love is something you just have to experience and define for yourself. On a whole, I’ve experienced it as being committed to someone I am passionately interested in. Someone who helps me discover aspects of myself I didn’t see before and for whom I can do the same. Someone I trust, respect, and share experiences with. Someone I can be my kind of weird with.

While this has certainly been the most unconventional romantic relationship of my life, Tim fits into all those categories. Even if it wasn’t meant to work for us romantically, I’ll continue to love him as a friend. I will be forever connected to him because of these experiences we’ve shared. We agreed that no matter what happens, we don’t want to lose each other from our lives. We’ve had four great years of friendship, 40 days of dating, and we will hopefully have many more crazy adventures to come.


Did you learn anything new about yourself?
I have so much respect for Walt Disney. I read a book about him recently, and his personality and life story remind me of Steve Jobs’s. Both were complicated and obsessive, layered with many personal issues, and were extraordinarily creative visionaries who ran successful companies. I’ve always thought that business and romance have many parallels. What I respect most about both of these men is not their ability to come up with numerous ideas, but to recognize which ones were worth pursuing, and to persevere through challenges and realize them. Like Steve Jobs said: “Deciding what not to do is as important as deciding what to do.”

How do you feel about this relationship/project right now?
We waited in line for a cab at the JFK taxi stand. At the beginning of the wait, Tim professed his hatred for Disney World. By the end of the line he professed his love for it. It is interesting to me how we can so easily shift between love and hate. Our moods and emotions and feelings can change from day to day, minute to minute. Our relationship with Disney World, like each other, was deeply conflicted and complicated. We are so wrong for each other in so many ways, and so right for each other in many other ways.

There were days Tim overwhelmed me and drove me nuts with his inability to make decisions and his constant need to exert control. Yet there were many other days filled with smiles, silliness, love, and laughter. We both learned a tremendous amount about each other and about ourselves. Just because it didn’t end as I had hoped doesn’t mean it wasn’t a success. The experiment forced me to reevaluate my lifestyle and what I want in the future. I am already happier, healthier, and more relaxed then I was 20 days ago. I was telling my friend about it, and he wrote me a nice message.


Is there anything that you want to do differently?
This experiment has made me extremely self-aware and confident in who I am, what I want, and what I am looking for. I don’t think there’s anything wrong with wanting a committed relationship. I know I can be very happy on my own, but life has always been even more awesome when there’s someone great to share it with. That being said, there is no rush, and I want to take some time to myself after this. I want to focus on my work, friends, and family. I have no idea what the future holds, but I am hopeful and optimistic about what’s next.

Additional comments?
We shared the cab ride home together. The driver dropped Tim off at his apartment first. We looked at the clock and realized it was 11:58 PM, making the 40 days come to an end at the exact moment we parted. We laughed at the irony. Tim jumped out of the cab, and grabbed something out of his luggage. He handed me a square package. A few weeks earlier when I was at The New Museum, I bought him a bound book of napkins that I thought he might like. He gave it back to me with illustrations of 40 things he likes about me. It was one of the sweetest and most thoughtful gifts anyone has ever given to me. And as if we were in some sort of twisted fairytale, he left me at the stroke of midnight with the gift and a goodbye kiss.

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Day Forty   /   lettering by Daniel Blackman

Timothy Goodman

Did you see Jessica today?

What did y’all do together?
We stayed in bed a while, cuddling and talking. It was really nice. Finally, we got up and went out to Animal Kingdom all day where we had a lot of fun. By the end, she got really sick from the combination of walking around in the heat and drinking alcohol. I practically had to carry her from the bus to the hotel lounge. Later, we hung out by the pool separately and I watched the Knicks lose to the Celtics. We got ready for our 9 PM flight back to JFK and headed out.


Did anything interesting happen?
We said one word on the way to the airport, and we said maybe two words on the plane. I could barely look at her on that flight. She was downing wine, and I was doing anything I could to stay distracted. I feel horrible about what happened last night. I just feel like such a disappointment to her and myself. It seemed inevitable that all the pressure would make this blow up. I just wish I could make this a happy story. I know she’s wanted that all along, and I’m sorry that I can’t give that to her. Our memories are a not a waste, though.


Did you learn anything new about Jessica?
She’s one of the best friends I’ve ever had. Today was very carefree, and it made me feel like a kid again. I guess sometimes we can be us, even for a day. We never talked about last night, instead we went strolling, drinking, eating bad food, sneaking into rides, and doing it all with ease. It reminded me why we’re such good friends in the first place.

Did you learn anything new about yourself?
Perhaps it’s all a self-fulfilling prophecy, just playing out my role as Jocelyn said, repeating the same pattern over and over again. I can see Jessie’s complexity and it scares the hell out of me. And the parameters of this experiment didn’t allow me to see things very clearly. This was like boot camp, and we learned stuff about each other that one wouldn’t normally know for a long time. Maybe we should have seen this coming the whole time. While I feel exhausted from it all right now, I also feel a real sense of hope for myself. This has completely challenged my personal life, the way I conduct myself, the way I approach relationships, how I consider the consequences of my actions, and my ability to let a woman into my life emotionally. I’m forever grateful for that.

I had something I made for her before the trip, but considering what happened last night, I didn’t know whether I should give it to her. Before heading to the airport she gave me an envelope that had the book When We Were Very Young by A.A. Milne in it. There was also a sweet card inside.


How do you feel about this relationship/project right now?
Ultimately I think we make a great couple on paper, but reality is a completely different story. Selfishly, part of me wishes that she could be more of an aggressor, someone who would try to convince me to change my mind just once. I know it’s not her style, but, selfishly, I wish her actions showed it as much as her words. Maybe she gives up too quickly. Maybe I want someone who’s gonna fight for me. Maybe that’s all BS, and I’m just making cowardly excuses. Maybe she just loves love. Maybe I’m just a scared little boy who can’t “man up.” Whatever it is, I know she deserves more. She doesn’t deserve someone who is unsure about her.

Is there anything that you want to do differently?
My whole life has been turned inside out from this crazy experiment. It’s 3 AM and I’m listening to the most ridiculous Phil Collins song right now. I don’t miss dating different women. I don’t feel like I’m missing out on anything, nor do I want to go back to my old habits. I do want to be in a relationship. I do want something meaningful. It’s been a while since I’ve let a woman in, and I do want to share my life with the right person.

Additional comments?
In mythology, once an adventure is over and the reward has been secured, the hero or heroine usually leaves the “special world” to go back to the world where he or she first began. The final test for the hero is to realize what they’re bringing back to the old world, literally or metaphorically. They have lived to tell their story, and to inform society. That gives me a lot of solace. While I do feel heartbroken right now, I feel a tremendous amount of hope for my future.

On the cab ride home, we barely spoke. We did, however, agree that everything would be okay no matter where we go from here. I thought of that Bob Dylan song where he says, “I gave her my heart but she wanted my soul.” And I know that what I could offer right now would never be enough for someone like Jessie. Jessie wants it all, and who am I to take that away from her? Who am I to string her along? I also know that I shouldn’t string myself along either.

As the cab driver pulled up to my apartment, we laughed because it was literally 11:57 PM as day 41 was approaching. I just can’t believe it’s over. I feel so close to her. I know now that I’m in love with her. I love her, yet I know there’s nothing else I can do. We kissed. I gave her a gift. We kissed one more time. I shut the cab door, and I walked away.