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CHAPTER 1

When We Were Young

Relationship patterns are a little like fingerprints — we all have them and each is utterly unique. Like it or not, we're all shaped in one way or another by our families, our childhoods, our upbringing. Here's a snapshot of where we came from, who we were long before we met, and how we became friends over the years. It may provide some insight into our relationship struggles.

OUR PAST

Jessica Walsh

What were you like as a child? I was a curious and inquisitive child with an active imagination. Among close family and friends I was confident, outspoken, and boisterous. My mom called me "Monkey," as I was always climbing and jumping on things, exploring the outdoors, looking for my next adventure. At home I was assertive and confident, but around new people I was timid and reserved. Being very shy made it difficult to make new friends, and I often felt like an outsider in school. I was also the black sheep in my family: the artistic, sensitive, intuitive child in a family of rational-minded left-brained thinkers.

What memories do you have of your parents? When my mother was pregnant with me, my parents quit their jobs and started a software company together. I grew up with their business. I watched throughout my childhood as their hard work and perseverance paid off. My parents taught us to focus on what we want and go after it. They told us to never settle and never give up. I think this approach has affected my outlook in many areas of life, including dating.

Who were your heroes or role models when you were a child? I always saw my parents as perfect role models whom I should aspire to. They had a successful marriage and a successful business. They had great friends and family and were always great parents to us. But while I admired them, I was also intimidated by them. I sometimes worried if I'd ever live up to their success. I spent a lot of time trying to please and impress them when I was younger.

Were your parents strict? At times when I was younger I felt frustrated by how involved my parents were. I was jealous of my friends who had no after-school commitments or had laid-back parents who set no curfews.

Looking back, I feel lucky I had parents who cared so much. They loved us, looked out for us, and truly wanted the best for us. I think in many ways they just wanted us to have all the experiences and opportunities they couldn't afford growing up.

What did you want to be when you grew up? When I was very young it was clear my passion was in art. I loved to draw and paint, but I never imagined I could make a career out of it. I always assumed it would be a hobby, and I'd follow in my parents' footsteps and go into business or sales.

When I was eleven years old, I became obsessed with computers and taught myself how to code websites and to use graphic art software. When I was twelve, one of the websites I created became very popular. I started making money off the site through advertising. I remember opening one of the large checks that came in the mail and thinking it was the greatest thing in the world that I could make money doing something I loved. This success as a child gave me the courage and confidence to pursue a career in design and the arts.

Were you a good student? Yes, I was a bit of a perfectionist in every aspect of life. I was one of those annoying kids obsessed with organizing books and class notes, color-coding folders, and always doing the extra-credit assignment.

Are your parents together? What is their relationship like? My parents found love at a young age and have had a long and happy marriage. So did my grandparents and great-grandparents. They have it all: shared goals and values, love, mutual respect, commitment, and attraction. They are not only lovers, but best friends, and were partners in all aspects of life, including their business. Throughout my childhood, there were almost no fights or major disagreements between them. They always respected each other, listened to each other, and supported each other.

Do you think your parents' situation directly influences your relationships? Having parents who were perfect models for how a relationship should be has made it hard to settle for anything less. This past year, my mom mentioned that I should be less picky or I might wind up alone. However, I know what I like and what I am looking for, and I'm not sure I'm ready to compromise. I am also aware that while previous generations of my family married young, I live in a very different time than they did. The Internet has popularized casual dating and hookup culture. Most people I know are focusing on careers, and marriage seems to be losing its relevance in modern times. All of this makes me wonder what it is that I really want, outside of the expectations from family and society.

Where did you go to college? My heart led me to the Rhode Island School of Design. I was dating a guy who lived in the area, and he had a big influence on my decision to enroll. While things between us didn't work out, I'm glad I ended up there. I really grew into myself during this time. I met great friends, gained confidence, and had amazing experiences. I also met my first true love in college. It was the beginning of sophomore year, and I fell for him at first sight. His upbringing was very different from my own: He grew up in a small hippy town in northwestern Washington. I was drawn to his unusually laid-back attitude. He taught me a new perspective on life and was unbelievably kind. From the moment we met, we rarely spent a day apart. We lived together and talked about getting married after school and one day having kids. For the longest time, I truly thought he was "the one."

When did you move to New York City? After college, I moved to New York City with my boyfriend. I started working at a design studio called Pentagram. It was my dream job, so I threw myself into the work, staying up all night, if necessary. Around this time, things started getting tough between us, and we began fighting more. I think deep down we both realized we wanted different things in life. He'd mention wanting to move back to the West Coast someday soon and start a family and live a simpler life. I was starting to realize that I wasn't really ready for marriage or kids and wanted to focus on my career. He moved on and eventually met a beautiful woman in Seattle, and they married and now have a kid. We've since become good friends. However, I've found myself comparing every new guy and every new relationship to what I had with him. It's been difficult to find someone who measures up to him.

What is difficult about dating in NYC? In a city filled with amazing men, you'd think it would be easy to find a great one. It's actually the opposite: Everyone here is too busy and thinks they can do better. I can be shy around new people, so I've had a hard time meeting guys here. A few years ago I tried online dating, and I did meet some great guys, but it didn't work out with any of them.

Do you like dating? Dating can be fun if you like the guy. I don't like to waste my time, or theirs, so I generally only go out with guys I really like, or with whom there's a real possibility for something more. I hate to sound so calculating, but even in online dating, I'll vet a guy thoroughly beforehand: Reverse-image searches on Google and Facebook makes that pretty simple these days.

What do you love about being in a relationship? It's not that I don't enjoy being single. I do. I just enjoy being in a loving, healthy relationship even more. It's nice to have someone you can give and receive love and support with. To have someone you can laugh, learn, grow, and explore the world with ... and cuddle with. Cuddling is the best.

When was your last serious relationship? My last serious relationship started in January 2010 and ended in January 2012. Besides my college boyfriend, it was the most serious relationship that I've been in so far. We were very much in love. We lived together, we adopted a dog together, and we talked about plans for our future together. One day I found out he had been lying to me for many months about some serious financial issues. While I tried to let it go, I just couldn't. I hold honesty above everything else. The relationship deteriorated, and I broke things off shortly after.

How do your relationships usually end? Most of them ended mutually and amicably, although I did break off a few. November 2012 was the first time a guy broke my heart. His name was Parsa. He was beautiful, intelligent, and mysterious, and I jumped into the relationship very quickly. Almost as soon as I fell for him, he broke things off. I was jolted by this; rejection is agonizing and embarrassing.

What are you looking for in your next relationship? After the last heartbreak with Parsa, I've also started to question why I wanted a relationship so much, and if I need one at all. Friends tell me I should slow down and enjoy being single, and at times I feel that way as well. But sometimes I feel restless, and something inside me doesn't want to give up on the search to find someone special. I am not so interested in marriage or kids yet, just someone wonderful and amazing to share life with.

When did you meet Tim? I met Tim five years ago in the design community in New York. It was right around the time I broke up with my college boyfriend. We always bonded over being the singles in a group of friends who were primarily couples. We'd hang out at least once a week or go for drinks. Our conversations were always focused on the crazy drama in our love lives. We'd listen to each other's stories, often dumbfounded at our polar-opposite views on love and relationships. We started to tease each other about these opposite issues. I'd call him a commitment-phobe; he'd call me a hopeless romantic. We started talking about these behaviors and patterns and started asking each other bigger questions about relationships.

What do you think about Tim's current dating life? Tim disappears on girls soon after things start to get serious. I don't think there is anything wrong with him dating around if he is honest about it, but I do think he is leading some of these girls on, whether intentionally or unintentionally. It would be great if he could develop a more mature perspective toward relationships, so that if he does meet a great girl he loves, he doesn't fuck it up. I do think deep down Tim is looking for someone wonderful.

When did you come up with the idea for the experiment? In December 2012, Tim and I had a trip planned with a bunch of our close friends to go to Art Basel in Miami. The morning of the flight, Tim and I were waiting in line at JFK airport, and we started talking about the most recent developments in our love lives. Parsa had broken up with me a few weeks prior. Tim, on the other hand, was telling me about the "stress" he was having from all the girls he was dating at once.

Tim mentioned the possibility of doing a project about our dating lives and failures. I immediately thought it was a great idea that would combine our love for design with our personal lives. Once we boarded the flight, we immediately started brainstorming. We talked about our opposite relationship issues and questioned how we could help each other or maybe even meet in the middle. By the time the plane landed in Miami, we had a pretty solid plan set for the experiment.

Why did you want to participate in the experiment? Whether it's romantic love, a love for my work, or love for my family and friends, it's that intense feeling of love, of believing in something or someone, that excites me and keeps me going in life. I've also never experienced any comedown or hangover that compares to being heartbroken. Yet no matter how much pain it causes, and no matter how many times it has destabilized me or broken me down, the pain eventually subsides, and the cycle starts all over again. Love is like some sort of socially accepted addiction, and I keep falling into its trap.

Someone once said that when you do the same thing over and over, looking for different results each time, it becomes a kind of madness. After some failed relationships, a painful heartbreak, and most recently a year of disastrous dating attempts in New York, where I was both getting rejected and doing the rejecting, I feel a bit lost, and am looking for some answers: Am I fucking up all my relationships, or have I not met the right person? Do I really want another serious relationship? Why do I jump into relationships so quickly? Why can't I enjoy dating more? How can love be so wonderful, powerful, and yet debilitating?

Of all the emotions or experiences I've had on this earth, love is the one I understand the least. The 40 Days experiment seemed like a perfect opportunity to explore some of my questions. I also wanted to challenge myself to face some of my inadequacies and fears in relationships and dating.

Was there an initial attraction between you and Tim? I am drawn to Tim in many ways. He's a great friend, he is a lot of fun to be around, and I respect him. While he's not my usual "type," I do think he is very attractive. Yet I've always been turned off by his dating style and track record with relationships. I've felt like it might not be worth taking the risk. However, I can't deny wondering, "What if?"

Were you nervous about the experiment? During our trip to Art Basel in Miami, we were having dinner with our group of friends when we told them about the experiment. They had a very negative reaction to the idea, and they pleaded with us to think about the ramifications. They thought we'd wind up hurting each other or breaking up our group of friends in the process. There was fighting and awkward stares, and the night ended in tears. Tim and I were pretty shocked at this response. The conversation made us stop and think: Was this experiment worth risking our friendship? Was it worth the possibility of splitting up our group of friends?

During the following weeks, Tim and I went back and forth several times about whether we should do the experiment or not. Finally, I sat down and really thought about it. Yes, it was a huge risk. It could be a total failure, it might ruin our friendship, and it would be emotionally difficult. However, I realized the even greater risk was not taking this chance and regretting it later.

I don't want to play it safe in life. I watch friends take on jobs they find boring only for the money, and I've seen friends settle into marriages because they worry they can't do better. Maybe those people will wind up happier in the end, but for myself, that version of life scares me. I don't want to wind up on my deathbed full of regrets for not taking crazy chances. I'd rather look back on a life of failures from these experiences than a life led by fear. This experience with Tim is really just a once-in-a-lifetime opportunity that I couldn't turn down or walk away from. So on February 20, 2013, we made our final pact to actually go ahead with this crazy idea. On March 20, 2013, we began the experiment.

Timothy Goodman

What were you like as a child? Growing up in Cleveland, Ohio, in a family of modest means, I learned how to be scrappy as a youngster. When I was seven years old I'd spend hours building things with my blocks. Then I'd aggressively tear it all down. When I was ten years old I turned my room into a "game room" where you'd walk through a path of board games I had set up everywhere. Then I'd tear it all down. When I was twelve years old I got into heavy metal. I'd buy tons of music magazines, put the pages up all over my wall in a very curated way, then tear it all down. To me, everything seemed ephemeral; nothing really meant anything. I was fascinated by that. But I'm still doing that: I build up romantic relationships, and then I tear them down.

Were your parents strict? For a long time, when I was really little, it was just my mother and me. She would let me watch stuff like Rambo, Eddie Murphy stand-up, and Cheech and Chong. At eight years old I could literally recite all of Eddie Murphy Raw. That might sound troubling to some, but my mom really turned me on to pop culture, and I think it's had a big influence on my work, not to mention helping me have a good sense of humor about things. I also ate too many sweets, like Lucky Charms, on most mornings. For fun, I would egg cars, steal from stores, and generally convince my friends to get in trouble with me. When I was an adolescent my older cousin, who was probably seventeen at the time, would spike my Coca-Cola at Thanksgiving. It was so much fun. But my poor mom. Jeez, I can't believe I came out relatively normal! No addictions, weird fetishes, or jail sentences.

Who were your heroes or role models when you were a child? My heroes were characters like Ferris Bueller and Zack Morris, and I reveled in the idea of pulling a fast one on people in authority. I really looked up to rebellious characters, as well as to pro athletes, and rock and rap stars. My three uncles on my mom's side were around and became my role models. For good or bad, they gave me some of the tools I needed to gain confidence in my life. While it was a bit hard to process while I was going through it as a child, looking back I'm thankful for them, partly because they were so eccentric and diverse. One of them was a mechanic. Another was a lieutenant general in the army. The third one was like a big brother to me. He's six-foot-six, and back then he had an awesome dog and a talking bird, and he was always single and lived in a different city. Finally, my wonderful and unusually hip grandparents have been a stable thread throughout my entire life.

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Excerpted from "40 Days of Dating"
by .
Copyright © 2014 Timothy Goodman and Jessica Walsh.
Excerpted by permission of Abrams Books.
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