Day Forty   /   lettering by Dana Tanamachi

Jessica Walsh

Did you see Timothy today?
Yes.

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.

animalkingdom2

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.

timandjessie

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.

Jessie

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?
Yes.

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 nine PM flight back to JFK and headed out.

Space

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.

disneystuff

Did you learn anything new about Jessica?
She’s one of the best sidekicks 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.

timfinal

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 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 three 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.


Day Thirty-Nine   /   lettering by Joshua Davis

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 Fantasy Land and went on the the Winnie-the-Pooh ride.

minnienew

I have an Alice in Wonderland obsession and I wanted to go on the Mad Hatter tea cup ride, but it was shut down for renovation. Around 2 PM, we wandered down Main Street. The street was lined with charming candy shops, ice cream shops, and bakeries. Tim and I split a large pistachio ice cream cone. We sat down near the sidewalk around three to watch the parade.

I have mixed feelings about this place. On the one hand, there is something fascinating about Disney World. There is a high level of detail to every aspect of the operation and the experience, from the hand painted signs and the technology behind the projections and holograms, to the large scale coordinated shows that happen like clockwork. Yet, as Prince Charming passed by us waving, and I watched the little children squeal in excitement, I couldn’t help but think there is something twisted about this place. This whole place just plants expectations in children’s minds that make them think they will grow up to meet the perfect person who will make all their dreams come true. While this kind of storybook love is a positive and a seemingly innocent notion, it’s nearly impossible to live up to.

It’s interesting to think about how this kind of true love is a relatively recent concept in human history. Marriage unions used to be treated in a much more practical manner, often as nothing more than a business arrangement between families. It was only in the last few hundred years that we saw this birth of romanticism throughout culture.

Did anything interesting happen?
Yes. It all began with a Mickey Mouse sweatshirt. We had dinner reservations at the Flying Fish Cafe on the Disney boardwalk. On our way to dinner, I realized my shoes were giving me a blister. I ran back to the hotel room to grab a new pair. We were almost at the train when Tim mentioned I would probably get cold without a sweater. He wanted me to go back to get one. I looked at the time and I realized we were already running late. I didn’t want us to miss the reservation, so I suggested we go to dinner and I would buy one on the boardwalk later.

disneysuperfinal

We enjoyed a nice dinner. I had scallops, and Tim had salmon. After dinner, Tim wanted to walk along the water to watch the performers and the fireworks. I was freezing cold, as Tim predicted, so we stopped in a tourist shop to get a sweatshirt. I finally found one I liked, looked at the tag, and made a comment about how pricey it was.

Tim got loud with me. He said I was forgetful and irresponsible, and that I should have listened to him. He said he didn’t understand what was wrong with me, and that it was no wonder I couldn’t save any money. I usually shut down immediately when I feel attacked, but I know how that annoys Tim even more. So I tried to stand up for myself, but this only pushed him further. Feeling defeated and unsure what to do, I shut down. I walked out the door towards the taxi station.

fight

After I walked out of the tourist shop, Tim ran after me and grabbed my arm. We sat down in the grass together. I asked him to think hard about what he was doing. Was he doing this as his usual defense mechanism? Is this his fear of vulnerablity? If so, I was willing to work through it with him. On the other hand, I’ve been completely open and honest with him about who I am, and what I can offer him. If he doesn’t think we are working romantically, then we should end this now and try to remain friends.

Did you learn anything new about Timothy?
All of Tim’s quirks and oddities seem adorable to me. The way his hair sticks up awkwardly after his sunglasses have been on his head for a while, how his pants are too short, how he eats too quickly and always leaves a mess. I even find it cute that he can become overly sensitive and takes things so personally. I find humor in these imperfections and accept him as he is.

Unfortunately, this is not the same for him. While we’ve been having a great two days here, Tim finds moments to slip in negative remarks. He said I’d be more attractive to him if I would gain more weight and have more curves. He said that he was bothered by how accommodating I am to him and his desires. He said I should pay more attention to my grooming. He said that it’s annoying that I don’t eat enough. He said it’s disgusting that my nail polish is chipping off. While I understand objectively where these comments are coming from, it still really hurts.

Did you learn anything new about yourself?
I had a relationship once where the guy fell very quickly for me. While I cared for him deeply, I knew he wasn’t right for me long-term. Even though I recognized that I was being irrational, everything about him increasingly bothered me, from his mannerisms to the things he did. It wasn’t the things that he was doing that were actually bothering me, it was him. I used these excuses as a way out. Is this what Tim was doing?

How do you feel about this relationship/project right now?
We continued to talk on the grass. He said he didn’t think it was a defense mechanism with me, but that he didn’t think we were right for each other. He said something about me rubs him the wrong way romantically. He said my strong feelings for him deeply worry him, and, like usual, I was moving too quickly. He said if we continued to date he would just fall back into his old habits and that he didn’t want to hurt me. He said I deserve more.

Is there anything that you want to do differently?
I told him I understood. However, I can’t deny feeling rejection and pain. I already loved him as a friend. After I allowed myself to open up to him and let my guard down, I’ve started to fall for him romantically. It seems I’ve repeated the same pattern again. I opened up too quickly, empathized too deeply, and I have another failed relationship to add to the list. I don’t know what to do or think at all anymore.

Additional comments?
How did this even happen? Are we completely over, or is this an argument that we’ll forgive and forget? I just want to escape the thoughts and feelings circling around in my head right now. When we got back to the hotel room, I took a sleeping pill with a glass of wine and went to bed. He crawled into bed behind me and held me, and we fell asleep together.

foreverover-small

Day Thirty-Nine   /   lettering by Mark Pernice

Timothy Goodman

Did you see Jessica today?
If I could play the guitar, I’d play the blues.

What did y’all do together?
I was crabby in the AM because I was hungry, but Jessie was full of energy. I ate a horribly disgusting breakfast, and I felt better. We hit up “Space Mountain,” “Splash Mountain,” “Haunted Mansion,” “Pirates of the Carribean,” and more. We even got our portraits done by a silhouette artist. The Magic Kingdom is an evil spectacle and I love it.

JT_Portrait

Early on, I encouraged us to cut into the “fast pass” line at the Pooh ride. The “fast pass” line is there if you got tickets beforehand. However, there’s a limit on fast passes you get. After the first cut, Jessie became obsessed and wanted to cut every ride. It became so much fun. We literally saved ourselves hours of waiting in line.

Did anything interesting happen?
We stayed for the parade at Magic Kingdom which is at 3 PM everyday. They do this massive production every single day, 365 days a year. Anyway, after that we went to the Grand Floridian resort to rest by the pool and have some drinks. However, things felt weird for me and our communication breakdowns were becoming more and more evident. Not to mention the conversation we had yesterday in the sauna started haunting me. As “40DoD-Day” is creeping on us, I realize I do have a responsibility to let her know how I feel. It’s Jessie, and I know how she needs to know. I know how she can’t live with this uncertainty as day 40 is hanging over us. I have to muster up an answer somehow. On a lighter note, I am so white right now! I could probably blind someone.

Legs

Did you learn anything new about Jessica?
Jessie wants love. She just wants to be a great girlfriend and to take care of her man. It just seems like she wants the perfect prototype to slide into her perfect boyfriend role.

Did you learn anything new about yourself?
This trip is making everything feel very serious to me. Usually, after two or three weeks of dating and being physical with someone, you don’t go on a trip together. At least not normally. There are times I have gone on trips a month into a relationship, but there’s been no pressure or countdown. However, it’s very natural for Jessie to go on a weekend trip this early in a relationship — sometimes even earlier than this! That’s just not me. I need time, and I don’t think she clearly understands that.

How do you feel about this relationship/project right now?
By the time we went to the Boardwalk resort for dinner, we were quiet and there was an awkward undertone to everything. Earlier, as we were leaving the hotel, I told her to go back and get a coat because it would get cold. She didn’t want to do that. So after dinner, she was chilly on the boardwalk and we stopped in a gift shop so she could buy a sweatshirt. As we were looking at sweatshirts she complained about spending the money. Then I got annoyed and reminded her that I had told her so. I know I was picking a fight, but she always backtracks on everything and then I have to listen to her complain the entire time. Well, she didn’t like what I had to say and she got loud with me. Then I got loud, and then we started arguing in the middle of the gift shop. Then she says to me, “You have issues! You’re fucked up! I’ve been so accommodating to you, and you don’t even care.”

After hearing that, I just threw the paddles in the lake. I’m sick of this. I basically told her that all I want is for her to STOP being so damn accommodating. Stop worrying about what I’m doing all the time. Stop worrying about being such a good girlfriend. This is something that has consistently been wearing on me, and it’s all come to a head now. All day she’s been worried about me like she’s my mother, constantly asking me what I want, what I need, who I saw, where I’ve been, how I feel, what I know, etc. I’m sorry, but it’s not attractive to me. I’ve talked about this before, how she puts her man before herself, and how that’s not my style. I just like a nice balance. I want to know that she knows who she is. I don’t want a partner who’s main objective is to be a great mate. I want to be with someone who can be herself, and someone who will let me be me without concern.

Tank

So here we are arguing on the boardwalk about this, and I can feel the whole relationship crumbling around my feet. She stomps away to go back to the hotel, clearly pissed off. But I couldn’t let her go. I stopped her and asked her if we could talk about it. The look in her eyes made me want to die. She said again that she really likes me, and that she really doesn’t feel like she’s getting that in return. And she’s right, I’m not giving it to her, at least not the last two days in Disney. I barely even held her hand today. And as much as I try to convince myself, it’s obviously not working for me.

balloon

While we were talking, she mentioned that a recent ex-boyfriend of hers loved all her little quirks and all the things that make her “her.” However, she broke up with him because she couldn’t stand all of his quirks. Ironically enough, she said that our situation was the same, except that I was her, and that she was her ex. She deserves someone who loves her for those things. All of her quirks should be adorable to me, but it’s sadly not the case here.

Is there anything that you want to do differently?
We calmed down and sat looking out at the water from the boardwalk. I couldn’t believe this was going down. It’s really over? It was as if I had no control, like some bigger force was making it all happen. We have such a kinship, yet there is so much friction between us. This dichotomy can’t be sustainable, I really don’t know what we can do differently at this point.

Additional comments?
We got back and sat in bed together. As we sat there, we started rubbing each other and kissing. I can honestly say I’ve never been more aroused in my life than I was at that moment. I wanted every single part of her, but there was so much guilt. She whispered, “should we have break-up sex?” I didn’t answer her, and we slowly stopped kissing. Ten minutes later we were asleep.


Day Thirty-Eight   /   lettering by Anthony Burrill

Jessica Walsh

Did you see Timothy today?
Bright and early!

What did y’all do together?
I hailed a cab at four AM and picked up Tim at his apartment. We headed to JFK and arrived at Jet Blue’s terminal for our six 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.

epcot

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 suppose 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 off of 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. Here is his personality portrait, and his psychological portrait.

cancer

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. Here is my personality portrait, and my psychological portrait.

scorpio

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

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:

publicfeelings

Timothy Goodman

Did you see Jessica today?
Oh yes.

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

Tickets

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. 20 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 10 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.

epcot2

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. High brow to low brow, 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 40. She told me that I don’t need to feel pressured to date her after the 40 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 40. 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?

why_how