What do you do when you’re tired of the prospect of dating? Two good friends with opposite relationship problems found themselves single at the same time. As an experiment, they dated for 40 days.

Love is a central theme in humanity across time and cultures. It’s one of the main topics in music, film, novels, poetry, and art. But what exactly is it, and why do we all approach it so differently? How does it affect us so deeply that sane people have gone mad over it?

The dating life in New York City can grow tiresome and wearing. Tim is afraid of commitment, often dating many girls at once, and he’s losing sight of what a healthy relationship means. Jessica is a hopeless romantic, jumping into relationships too quickly, always looking to find “the one.”

It’s been said that it takes 40 days to change a bad habit. In an attempt to explore and hopefully overcome their fears and inadequacies, Tim and Jessica will go through the motions of a relationship for the next 40 days: the commitment, time, companionship, joys and frustrations. Can they help each other, or will they fall into their same habits? Will they damage their friendship? What if they fall in love?

Questions for Jessica

Why did you participate in this experiment?
All my relationships keep failing. Am I fucking them up, or have I not met the right guy? Tim and I have been friends for years, and we always make fun of each other about our relationship problems. I wonder if putting two people together with opposite issues could help. Plus, these problems seem to be common with many other girls and guys we know, so I want to learn more about love and relationships in an attempt to figure out why.

Do you like dating?
I prefer being single or being in a relationship. Dating can be fun, but it can also just be painfully awkward.

What is difficult about dating in NYC?
Everyone 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. For a long while the only interest I was getting was from a construction worker who would catcall near 15th street. Eventually I tried online dating, and I did meet some great guys, but it didn’t work out with any of them.

When was your last serious relationship?
It ended a year and a half ago. It was painful since we were very much in love. We had many wonderful years together, we lived together, and we had a dog together. However, after discovering he was lying to me for months, the relationship deteriorated.

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 unintentionally. It would be nice if he developed a healthier perspective towards relationships, so if he does meet a great girl, he doesn’t fuck it up.

Do you really need companionship or do you just hate being alone?
I do enjoy being single. I just enjoy being in a loving healthy relationship even more.

What do you love most about being in a relationship?
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.

Are your parents together? What is their relationship like?
They married young at age 23 and have been together for 30 years. They have a very loving and supportive relationship. They are each other’s best friend.

Do you think your parents’ situation directly influences your relationships?
My mom said that I am getting older and I should be less picky or I might wind up as a lonely cat lady. But I know what I like and what I am looking for, and I don’t want to compromise. I just hope I can find a “partner in crime” like my parents did. I am not so interested in marriage or kids yet, just someone wonderful to share life with.

Are you nervous about this experiment?
Of course I am nervous, as I have no idea what the outcome will be. But I am always up for strange experiences and crazy experiments!

Questions for Timothy

Why did you participate in this experiment?
On one hand, I’m having the time of my life. On the other hand, my inability to commit concerns 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. Furthermore, we’ve been the single individuals in our group of friends for awhile, which has allowed us to bond over our shortcomings.

Do you like dating?
Usually, yes. I’m very comfortable around all types of women, and I love the thrill and parody of it all. The other day I saw a guy walk up to a woman and start a conversation. He did not know her. He didn’t meet her on the internet, this was the middle of the day in a public place. Yet, he built up the courage to talk to her. That’s a lost medium that 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.

When was your last serious relationship?
About two years ago. Since then I’ve been on cruise control. I think everybody reaches a peak in their life when things line up: confidence, age, success, and an ease about the opposite sex. I am not anti-relationship, I just don’t think I’ve met the right person. I might as well have fun in the meantime.

What do you think about Jessica’s current dating life?
Jessie broke up with a long-time boyfriend a year and a half ago. 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.

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.”

What do you love most about being single?
Freedom. Why are the majority of single women I know disappointed, and the majority of the single men I know are having a blast?

Are your parents together? What is their relationship like?
When my mother was 3 months pregnant, my father (her then boyfriend) told her that it was him or me. Thankfully, she chose me. I am certainly not devoid of issues.

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 the wonderful mentors and male influences in my life—and for that, I wouldn’t trade anything.

Are you nervous about this experiment?
A bit nervous, a bit excited, a good splash of curiosity. We’re playing with fire. We’re playing with a good friendship.