Jessica Walsh and Timothy Goodman face up to issues in a relationship experiment.
© Osvaldo Ponton

Come Face-to-Face and Gain Perspective

Jessica Walsh and Timothy Goodman had a creative idea. Date for 40 days (long enough to break bad habits) and work on issues that had gotten in the way of prior relationships.

Friends for four years, Jessica and Tim are designers in NYC, people who take creative risks and enjoy collaborative projects. They have a lot in common, but—

Jessica loves the thrill of healthy, romantic relationships, falls into them perhaps too quickly, and is looking for “the one.”

Tim loves the thrill of the chase (often dating several girls at once), has trouble committing, and sometimes leaves relationships for trivial reasons.

With these opposite perspectives, Forty Days of Dating is a relationship experiment with potential for explosive results. Will the friends damage their friendship? Will they fall madly in love? Will they gain perspective?

“Embrace uncertainty,” good watchwords for a relationship experiment
© Anisa Suthayalai

Getting Starting

For the experiment, Jessica and Tim set rules, such as seeing each other every day, visiting a couple’s therapist weekly, and filling out a daily questionnaire privately and with candor.

The 40 days occurred last spring, and now from July 10–August 16, 2013, daily posts chronicle the developments. Typographic art from friends captures the essence of each day, staring with Day 1:

Day 1 for Tim after a date the night before 
© Roanne Adams / Roandco

Day 1 for Jessica: When an opportunity seems scary, I must take it.
© Keetra Dean Dixon

Insights Galore

Now, more than half-way through the project, the couple’s daily reflections offer a treasure trove of “Oh, I see” moments. Here are but a few:

1.  On the Role of Exes— 

On Day 5, Jessica and Tim engaged in “art therapy,” making word pictures about past relationships while they shared ginger cookies and egg pastries. When Jessica moved her exes out of her head, she found it “surprisingly therapeutic.”

Jessica gets an ex out of her head and onto paper.
© Jessica Walsh

Tim drew his dating history of 65 girlfriends and observed, “There’s something liberating about airing my dirty laundry.”

With 65 on his dating list, it must have taken time for Tim to air his dirty laundry!
© Kate Moross

2.  On Why People Fall Too Fast— 

A visit to a couple’s therapist on Day 8 gives insight on Jessica’s issue. Looking at the portraits of her exes, it’s easy to see that she jumps into relationships. The therapist explains and Tim, at least, has an aha moment:  Jessica gets serious so fast because she dislikes the discomfort or awkwardness in the beginning of a relationship.

3.  On Avoiding Attachment—

On Day 11, Tim gets crabby and starts pointing out Jessica’s quirks and weaknesses. She recognizes Tim’s behavior as a way to protect himself from getting too attached.

Jessica Walsh
© Forty Days of Dating

On Day 13, Jessica explains:

“As soon as he starts seeing a girl, especially a girl he really likes, he’ll focus on bizarre things about her that bother him.

“These things are meaningless in terms of a relationship, but he claims they are deal breakers.

“A few months ago he dated a great girl who seemed to have it all, but he decided he should end things because he didn’t like her shoes. Seriously.

“The next girl he said he liked hooked up with him too soon. The next girl he dated was amazing but she didn’t like her career as much as he likes his.”

The attachment issues led to the first fight, and soon the couple had to—

Not even two weeks into the relationship, things began to change.
© Sabine Dowek

4.  On the Fear of Commitment— 

Jessica reports mixed signals from Tim: “He’s both interested and scared to become intimate, yet he’s still being flirtatious and showing signs of wanting more.”

She starts asking more from the relationship. What does that feel like to Tim? He speaks honestly:

Timothy Goodman
© Forty Days of Dating

“I feel like I’m walking on eggshells a bit.” (Day 12)

“Yes, I am interested in more, but it just feels too risky.” (Day 13)

“I feel a lot of pressure from Jessie. I like a bit of uncertainty, and I like living in the questions. I don’t like having to live up to some idea, or to fulfill some expectation, though. I don’t think she even realizes she’s doing it. The whole situation is making me feel very unsettled, and she wonders why I’m being so wishy-washy.” (Day 14)

The pressure Tim feels leads to the wishy-washiness that confuses Jessica, and that confusion prompts the questions that feel like pressure to Tim. Ah, it’s a circle all about commitment. What’s missing?

What do the missing letters spell?
© Leland Maschmeyer

5.  On Not Giving Up—

As in all relationships, things get really tense. On Day 15, Jessica decides to quit the project, but returns.  On Day 23, Tim has had it:

“I’ve never felt more like a mouse in a cage being tested on against my will. I feel grimy. I feel very uncomfortable. I feel emotional.”

And Jessica is deflated.

What gets them through it? Intense communication and this realization:

Full hearts and broken hearts happen as relationships go ’round.
© Sharon Hwang

What’s Next?

By Day 24, Tim has decided to give the relationship a go. Jessica has decided to let go of her expectations. They have sex. It’s 15 days from today to the end of the relationship experiment. Find more of their candid “Oh, I see” moments at 40 Days of Dating, and gain perspective for yourself, too.

Jessica is a partner at Sagmeister & Walsh, and Timothy runs his own design studio.

Comment on this post below, or inspire insight with your own OIC Moment here.