40 Days of Dating: An Experiment

by Jessica Walsh

  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.

  Were you a good student? I was a really horrible high school student; I barely graduated. That’s how my graphic design career started: In high school, I would steal hall passes, replicate them in Microsoft Word, and print out whole packs of them. Later, I forged teachers’ signatures. I was a cheater. At one point, I skipped Spanish class twenty-eight days in a row and had a 0.7 GPA. I was all about partying, and I had no focus. I regularly smoked weed throughout my junior and senior years. I even got suspended on the last day of my high school career. I took it all in stride; actually, I thought it was funny. When all my friends went to college, though, losing them depressed me. It was a reality check, and I began to look at my life in new ways and ask myself different kinds of questions.

  What did you want to be when you grew up? It’s funny, I don’t remember wanting to be anything in particular. There was an old man in my neighborhood, back when I was growing up, who would call me Dead End Kid, a reference to the characters played by teenage actors in the Broadway play Dead End in 1935. They were newsboys who smoked cigarettes and their faces were always covered in dirt. I was sort of a 1980s version of that. I do remember, for a brief moment, wanting to be a police officer. And I remember really liking the label “cop.” My friends and I would play around in the neighborhood—hopping fences, running through backyards, climbing up on garage roofs—and in the movies, cops would do this kind of activity as they were chasing the bad guys. I really liked the idea of that. Not catching bad guys, but hopping fences and running through backyards. I was a dust kicker.

  Where did you go to college? After barely graduating high school, I started working for a guy named Dave who ran a painting and home improvement company. He was my first great mentor and is still like a father to me to this day. In the beginning, I was a laborer, hauling buckets of wallpaper glue up ladders for twelve to fifteen hours a day. That taught me a strong work ethic. It also has helped me appreciate how fortunate I am to be doing what I love, and how lucky to be doing it in New York. I try not to take anything for granted. I think one reason I acted out so much as a kid was because I was missing that kind of father figure in my life, so it was a really profound experience to have Dave fill that void. Over the next four years, he taught me fundamental skills like painting, tiling, and drywalling during the day, while I took interior design classes at Cuyahoga Community College at night. I had to take a lot of different classes for my major, but my drawing teacher, Nancy Halbrooks, was especially supportive. She encouraged me to keep drawing, which then led me to study design with a teacher named Jacqueline Friedman. She was very demanding, and that gave me confidence at what I was doing, and I soon realized that I wanted to get out of Cleveland and move to a bigger city.

  When did you move to New York City? I moved here when I was twenty-three to go to the School of Visual Arts. Being older, I kind of treated it like a job. I felt that I had this one shot to make something of myself, or else I would have to move back to Cleveland with all of these loans and start painting houses again.

  What memories do you have of your parents? My mother taught me how to love and respect people, which is why I have so many meaningful and lasting friendships. She struggled at times, but she was strong. It was good for me to be around that. When I was twenty-one she was diagnosed with thyroid cancer, and I watched her overcome that. I learned that a woman doesn’t need money to be strong, she just has to have love and faith. When I was twelve years old I vividly recall my mother hiding a roll of money with a rubber band around it in my sock drawer. It was about two thousand dollars, and it was all the money she had to her name. She did this because things started going bad between her and my stepfather, and she was worried about the future. This formed the basis of my relationship with money: I wouldn’t say I’m cheap, but no matter how much money I make, saving is important to me. When money is tight, all you have is the idea of the way things could be. This made me crave success, I think.

  Are your parents together? What is their relationship like? When my mother was three months pregnant with me, my father (her then boyfriend) told her she had to make a choice between him and me. Thankfully, she chose me. We didn’t have any money, and we lived on the second floor of a duplex house. Someone told me that when I was a baby she had been on welfare and worked at a gas station. When I was five years old she married a man and they had two sons, giving me awesome brothers. When I was thirteen she divorced him, and when I was sixteen she married a really great guy, and they’ve been together ever since. I’m glad she finally found someone.

  Do you think your parents’ situation directly influences your relationships? Had I grown up in a more traditional family structure, I might have approached things differently. However, I wouldn’t be who I am today without my mom, my grandparents, and the mentors and male influences in my life—and for that, I wouldn’t trade anything in the world.

  Why can’t you commit? I’m a big fan of Winnie-the-Pooh. There’s a quote where Owl says, “A girl sees what she likes, a boy likes what he sees.” I guess I’m a little like a kid in a candy shop, liking what I see. I don’t believe I can’t commit; I just haven’t met the right person. In many situations, commitment sadly translates to compromise.

  What do you love most about being single? Freedom. The other day a friend of mine called me an “accidental player.” She meant that I don’t have an agenda when I get involved with women or have a need to add another notch on my belt. I just love meeting new people, and I love the company of women. But I admit I do find myself in these situations where I’m leading the woman on. I’m not trying to, but I realize I should hold myself back sometimes and exercise more restraint. When I become infatuated with someone in the beginning, I just love that dynamic, and it’s hard to turn it off even though I may already be aware I’m not going to fall for that person.

  Do you like dating? Yes. I’m very comfortable around all types of women, and I love the thrill of it all. The other day I watched a guy walk up to a woman he didn’t know and strike up a conversation with her. He didn’t meet her on the Internet; this was in the middle of the day in a public place. Yet he built up the courage to talk to her. Walking up to a stranger is a big risk. That’s a lost art these days, but when you can work up the nerve to do it, the experience can be truly magical.

 
; What is difficult about dating in NYC? I think the dating life here is only difficult if you’re looking to settle down. If you’re looking to date, it can be perfect. Everyone is so career hungry, and it’s hard for some men to stay focused when there are beautiful and interesting women everywhere. That said, I think there’s a similar problem for women. I have many female friends who are in the “I’m single and I don’t need a man” phase, refusing to recognize a great guy in their life.

  When was your last serious relationship? About two years ago. Since then I’ve been on cruise control. I’ve had several long-term relationships (three years was the longest), been in love, and lived with women. But now that I’m a bit older, I feel like I’m much more in tune with my tastes. I think everybody reaches a peak in their life when everything aligns: confidence, age, success, and an ease about the opposite sex. Right now I feel like I’m close to, or at, the peak. Perhaps I fear commitment because I’m afraid it would compromise my place at the peak. Thing is, I am not anti-relationship; I just think I haven’t met the right person yet. In the meantime, I might as well have some fun.

  When did you meet Jessie? We met on email in October 2008. Jessie worked for Print magazine in NYC, and they were featuring my work in the magazine. She emailed me to get some images. After an informal conversation on email, I Googled her and thought she was really pretty, so I tried to stir up more casual conversation via email. I found out Jessie went to RISD, and I remember saying, “You seem so lovely and fun—I thought only self-deprecating people went there!?” I like to think that she was charmed, but probably not. From there, we started talking and hanging out more, but it was always just a friendship.

  Was there initial attraction? Yes, for me there was. I’ve always been very attracted to and curious about Jessie and her mysterious ways. But I always really respected Jessie and her work, and she’s one of my best friends. I didn’t want to risk screwing that up. There was a healthy curiosity and an attraction before we started the 40 Days experiment; otherwise we probably wouldn’t have agreed to do this together. She’s the complete opposite of me—much more reserved and pragmatic—but we also have major things in common. Many people thought Jessie was participating in this experiment as an excuse to date me, and that I was doing this because I wanted to sleep with her, which is ridiculous, because if that were the case, I would have already tried to sleep with her! I’m not saying I would have been successful, but I definitely would have tried.

  What do you think about Jessica’s current dating life? Jessie broke up with a longtime boyfriend in late 2012. Since then, she’s been juggling the dating scene and the single life. Ultimately, she just really wants to be in love. I don’t quite understand her rush, but it’s important for her. I’ve tried to encourage her to have some fun, date around, and let go of the expectations.

  When did you come up with the idea for the experiment? It was an early Friday morning on December 7, 2012. We were waiting in line for egg sandwiches at JFK airport on our way to Art Basel in Miami with a group of friends. Jessie was telling me how heartbroken she was about a guy who called it quits a few days earlier. She had only been dating him for a month, yet she already had very strong feelings for him. After a few minutes, the conversation quickly turned to me and my own dating problems. I was dating several girls at the same time and was feeling kind of stressed about it.

  Why did you participate in this experiment? On one hand, I’m having the time of my life being single. On the other hand, my inability to commit does concern me. I think this project is crazy and wonderful and risky, and Jessie is the only person I know who’s as crazy and risky as I am. Furthermore, we’ve been the only single individuals in our group of friends for a while, which has allowed us to bond over our shortcomings. And, naturally, like everyone, I’m obsessed by the idea of love. It affects every human being and has for all time. For starters, the Bible is full of verses and passages about love. In Roman mythology, Venus, the goddess of love, is the mother of the Roman people. Shakespeare’s Romeo and Juliet has become a synonym for love. Gone with the Wind earned more money than any other film in box office history. And Phil Collins has sold over 100 million albums singing about love and heartbreak!

  Were you nervous about this experiment? A bit nervous, a bit excited, a good splash of curiosity. It felt to me like we were playing with fire. We’re playing with a good friendship. It took weeks for us to build up the courage to do this. And through the same technology that many of us spend much of our lives using, and that many of us brush off as a detriment to modern dating, we wanted to throw ourselves into an experience that was very traditional. We wanted to make ourselves vulnerable but in a situation that is familiar to us all. We wanted to explore what it means to search for love, for what you want in a partner, the consequences of successful or failed relationships, and, hopefully, through this bizarre experiment, give ourselves the chance to change our “bad habits” in love.

  SCHOOL ASSIGNMENT, 7 YEARS OLD

  SCHOOL ASSIGNMENT, 6 YEARS OLD

  DATING TIMELINE

  The assumption that we should fall in love before getting married is a relatively recent notion. Throughout most of history, up until the nineteenth century, marriage was seen as little more than a practical union, a contract between families to secure power and money that was set up by the parents. Dating, as we know it today, was virtually unknown until around the 1920s, the Jazz Age, when traditional mores began to loosen. Things opened up even more in the 1940s (post-WWII) and the 1950s. Ever since, dating protocol has continued to evolve dramatically. In the early days of dating, we met through family, friends, and our local communities. The digital age in general, but especially the Internet, has had profound effects on how we get together and communicate our feelings. We’re convinced that 40 Days of Dating could never have happened without our cell phones, computers, and social media. But let’s go all the way back to the beginning, starting with the very first couple, Adam and Eve.

  WAY BACK

  God creates Adam from dust and places him in the Garden of Eden. God places a tree in the Garden of Eden that he prohibits Adam from eating. Then Eve comes along, and the rest, as they say, is history.

  ANCIENT TIMES

  In ancient times, many of the first marriages were by capture, not choice. When there was a scarcity of nubile women, men raided other villages for wives.

  1491 BC

  The first recorded marriage is in ancient Egypt in around 1491 BC between Thutmose II and Hatshepsut. They were between the ages of twelve and fifteen.

  270 AD

  On February 14, 270 AD, Valentinus, later to become St. Valentine, is beheaded. Legend has it that before his execution he wrote a note to the daughter of a jailer and signed it “from your Valentine” as a farewell.

  496 AD

  In 496 AD, St. Pope Gelasius I declares February 14 “Valentine’s Day.”

  EARLY 500s

  King Arthur, Lancelot, and Guinivere make the love triangle stylish. Arthur and his Round Table of knights create the template for courtly love and chivalrous behavior.

  7th CENTURY

  Christian churches begin to take a more active role in the marriage process. In the centuries prior to 1000 AD, marriage is a good way to ensure your family’s safety.

  12th CENTURY

  The union between a man and a woman is described in the sacred texts of most religions. The Catholic Church in Europe becomes more involved, performing ceremonies and dictating who can get married.

  1228 AD

  Women first gain the right to propose marriage in Scotland, a legal right that then slowly spreads through Europe.

  18th CENTURY

  The first personal ads, like this one, appear in papers. “To the ladies: Any young Lady, between the Age of Eighteen and Twenty-three, of a middling Stature; brown Hair; regular Features, and with a lively brisk Eye; of good Morals, and not tinctur’d with any Thing that may sully so distinguishable a Form; possessed of 3 or 400l., entirel
y at her own Disposal, and where there will be no necessity of going thro’ the tiresome Talk of addressing Parents or Guardians for their Consent...”

  1837–1901

  During the Victorian Era, romantic love is viewed as the primary requirement for marriage, and courtship becomes even more formal, almost an art form, among the upper classes.

  1882

  In 1882, England passes the Married Women’s Property Acts, which allows women to keep money they earn during marriage and to inherit property under certain circumstances.

  MAY 28, 1927

  Rotary dial service begins and men start calling women on the phone.

  SEPT. 12, 1944

  Barry White is born. He goes on to make hit songs like “Can’t Get Enough of Your Love, Babe.” More babies are conceived.

  1950s

  With the rise of the automobile, dating becomes enormously popular.

  1960

  The Pill is released in the U.S.