Day Five   /   lettering by Stefan Sagmeister

Jessica Walsh

Did you see Timothy today?
Yes, we spent most of the day together.

What did y’all do together?
Relationship art therapy. We made illustrations and wrote out memories based on past relationships or people we’ve dated while eating ginger cookies and egg pastries.



Did anything interesting happen?
Getting your exes out of your head and onto paper is surprisingly therapeutic.

Did you learn anything new about Timothy?
Yes, I learned that he’s been on dates with over 65 girls. What a man whore.

Did you learn anything new about yourself?
I’ve been on dates with 12 different people in my life. I’ve kissed 11 guys and one girl. I’ve had two serious long-term relationships. I’ve had three semi-serious relationships. I’ve slept with eight guys. I’ve lived with two boyfriends. I’ve never had a one-night stand. I’ve been in love twice. I’ve been more dates this past year than the rest of my life combined.

More about my past relationships, flings, and mistakes:

She was my first kiss and my first relationship. I dated her while I attended an all-girls boarding school when I was 13. My parents found out and they were very upset. They’ve always been open-minded and supportive, but they said that I was too young to know if I was a lesbian. They were right.

He was a close friend’s older brother. We dated in high school for a year. Something unfortunate happened the first night we were together. We both tried to put it behind us, but it eventually broke us apart.

My college sweetheart. We fell madly in love almost instantly and didn’t spend one night apart for six months straight. We lived together for two years. I’ve kept every handwritten letter I’ve ever received, so I read through his old love notes to me today. It made me realize he was too good to me, and had made my happiness a priority over his own. We separated after college, and have since stayed good friends.

I met him through my high school best friend. We became very close when I moved to New York City. He’s a very smart and talented designer with a laugh that’s equally embarrassing as mine. We separated on good terms and he is now dating the high school best friend.

We were coworkers. He dated my close friend who was living abroad at the time, but they broke up while she was gone. We were at a work party a few weeks later when he kissed me. I liked him, but I didn’t want to compromise my friendship with my girlfriend, so nothing more happened.

A Swiss-Croatian film director. He kept asking me out over email after we featured him in a design magazine I worked for. One day I stumbled across an interview he did with the BBC, and I fell in love with him before we even met. It was those intense dark eyes and his cerebral mind. We moved in together only a few months after we started seeing each other. Our relationship was passionate and deeply emotional. A few years later I found out that he had been lying to me, and it broke us apart.

He is a very kind and outgoing Cuban photographer who loves the nightlife. He taught me to live a little more, to smile more often, and to dance. We ended the relationship four months in, but have stayed good friends.

A tall and handsome Persian architect who I fell for way too quickly. We’d exchange long romantic letters almost daily. We’d stay up late making music playlists for each other. He called me “Honey Bunny”, and I called him “Darling.” He broke it off quite suddenly, and I was devastated. There is nothing more painful than being rejected by someone you adore.

He was a tall guy from Rhode Island who had an unusually thick beard. He designed quirky furniture and liked to drink whisky on the rocks. We went on a few dates, and spent New Year’s Eve together. I have not heard from him since.

A handsome ER doctor who loves to surf and take photographs. He told me that he was accepted to a residency program at a hospital in Australia and would be leaving in six months. At the time I didn’t want to risk getting close and possibly hurt.

We had long late night chats before we even met. We’d throw around crazy ideas for personal projects we could do together. On paper he seemed to have it all. He was a gorgeous underwear model, an architect, and a furniture designer. He was kind, smart, and owned the cutest dog. But when we met in person, our personalities didn’t click. I became very shy, and he talked too much to compensate.

A good looking math genius and professional poker player. The first night we met he took me to the SoHo House, and he asked me to be his date for the opening night of a big tournament in Las Vegas. I’m a sucker for crazy, spontaneous proposals. We boarded the plane a few days later.

How do you feel about this relationship/project right now?
Good, we had a really nice day. I used to collaborate creatively with my college boyfriend quite often, and this is something I missed in my last few relationships. It reminds me of the Charles and Ray Eames philosophy: Life is work is life is work is life. I am so grateful my work is my play and my hobby. The whole ‘life and work balance’ concept always seemed so overrated.

Is there anything that you want to do differently?
We’ve taken the term “personal project” to a new level. I like that. I want to do more projects that test this boundary.

Additional comments?
While all these romantic relationships have come and gone over the years, the relationship with my work is constant and never fails me. I was talking to my mom about this. She told me that as a child, I was always at my happiest when I was creating things. She dug up this old essay I wrote in school and mailed it to me.


Day Five   /   lettering by Kate Moross

Timothy Goodman

Did you see Jessica today?
You know it.

What did y’all do together?
We met in the morning. The plan was to spend the day illustrating our dating history.

Did anything interesting happen?
While we’re both familiar with each other’s dating history, I have never dissected it quiet like this. Jessie made me write out every girl I’ve gone on a “date” with, and there’s something liberating about airing my dirty laundry.


Did you learn anything new about Jessica?
We work really well together. We’ve already been working together for the last month — discussing and strategizing a lot of things surrounding this project — and I realize that I am NOT sick of working with her yet.

Did you learn anything new about yourself?
Going through my dating history was a bit daunting. Jessie thinks I’ve gone out with a lot of women, but I don’t think it’s that big of a deal. I have friends, both men and women, who have gone out with more people than this. The bulk of my history has been in the last six years, since I graduated college.

Some moments in history:

She was half-Vietnamese and half-French. She had a large Buddhist scripture on her back, sort of like Angelina Jolie’s tattoo. She started calling me “baby” on the first date. That’s when I knew it was over.

I was traveling to Vegas for work, and so was she. She sat behind me on the plane. We had a fun couple days.

She was a Lower East Side girl, a Renaissance woman, always on the hustle, full of great energy. I was really into her until she told me she talked to aliens. Seriously.

I really liked her. She wasn’t over her ex-boyfriend. I was disappointed that she ended it so soon.

She was stunning: Northern European, tall, stylish, educated and charismatic. She also partied way too much, and was always looking for the next thrill. She was done with me after a month.

First dates are the perfect time to be spontaneous. After a couple months she was disappointed that I was working so much.

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 spirit. 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 one or two women 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 a good friend to me, and 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.