Politics & Policy

Forty Days of Dating

Timothy Goodman and Jessica Walsh don’t do online dating, but they dated online.

There was a time when the idea of thousands of people reading your diary would have been mortifying. That time has passed. Now, it’s called blogging, and, as Timothy Goodman and Jessica Walsh have seen recently, it can be the fast pass to your 15 minutes of fame.

Timothy and Jessica are attractive, successful graphic designers living in New York City. They’re almost perfect stereotypes of urban millennials: They’re hip and career-focused, ostensibly liberal politically, and they seem to survive on some combination of take-out and alcohol. They’re eager for experiences, and they obsessively document those experiences (to invoke a useful Urban Dictionary phrase, “Pics or it didn’t happen”). In the past several weeks, Timothy and Jessica have become Internet celebrities, as their blog, Forty Days of Dating, went viral.

Back in the spring, Timothy and Jessica, friends for four years, found themselves single at the same time. Tired of the New York City dating scene, they decided to do an experiment, turning the classic When Harry Met Sally question — can men and women be just friends? — on its head. Instead, they would see if two friends could be something more — and blog about it. They would “go through the motions of a relationship” for 40 days in an attempt to learn about love and to work through the problems they have had in past relationships. 

The rules for the project were simple: They would see each other daily, go on at least three dates a week, see a couples therapist once a week, go on a weekend trip together, “not see, date, hook-up, or have sex with anyone else,” and document it all. Forty Days of Dating went live in mid-July, and on September 6, the duo published their final post, revealing that, at the end of the experiment, they broke up.

On the surface, the project doesn’t seem all that interesting. Tim and Jessie suffer from pretty typical relationship problems. Jessie is a self-described “hopeless romantic” who tends to jump into relationships, and Tim is commitment-averse. Each day they answer the same set of eight questions: Did you see (Timothy/Jessica) today? Did anything interesting happen? Did you learn anything new about yourself? How do you feel about this relationship/project right now? etc. Their blog posts read like journal entries, and often rather whiny, self-absorbed journal entries at that. And, let’s be honest, that’s not a description of particularly engaging reading material. 

But there are several reasons why Forty Days of Dating has garnered so much attention. One reason for its success is that it’s incredibly well designed, clean and visually interesting. Dozens of Tim and Jessie’s friends and colleagues contributed “type treatments” (graphically designed typography) that relate to each day’s content, such as the following:

The blog functions like a virtual scrapbook, featuring short videos and snapshots, receipts from dates, even the condom wrapper from the first time Tim and Jessie sleep together (“I knew having condoms as business cards would come in handy one day,” Jessie writes).

Another reason for the blog’s success is that, in a culture where old-fashioned dating seems to be dying out, and the hook-up culture and online dating seem to be taking over, Forty Days of Dating is surprisingly traditional. Tim and Jessie don’t even hold hands until Day 18. And while they are documenting their dating experience online, they aren’t online dating. “We no longer search for our romantic partners; we shop for them,” Jessie writes on Day 10. And she’s right. One-third of U.S. couples who married between 2005 and 2012 met online, according to a recent study in the Proceedings of the National Academy of Sciences. There’s nothing wrong with that — many happy relationships are formed through online dating — but it is indicative of a cultural shift. 

Of course, Tim and Jessie’s relationship isn’t strictly traditional either. Most couples don’t see a couples therapist during the first week of a relationship (theirs sagely tells them, “Emotions know no project boundaries”), or spend $160 on ginger mojitos for a weeknight date, or consider an afternoon spent illustrating their dating histories together to be a good time. But there’s something refreshing about Forty Days of Dating, and that is that Tim and Jessie are friends and that they go on fun dates, write each other sweet notes, and recognize how important the small things are in a relationship. Further, in a time when vulnerability is often considered a sign of weakness, they’re willing to be honest with themselves and with each other. 

Perhaps the most interesting part of the experiment, though, is the way Tim and Jessie analyze their own approaches to relationships in comparison with their parents’ experiences. Jessie’s parents got married in their early 20s and have had a stable marriage for 30 years. Because she wants to have a successful marriage like her parents, Jessie puts a lot of pressure on herself. “What is so wrong about seeking a healthy, committed relationship?” she writes. There’s nothing wrong with that, but Jessie is part of a generation that thinks committed relationships come at the expense of their careers and of “keeping their options open.”

Tim grew up in a chaotic family situation. When his mother was three months pregnant, his father (her boyfriend at the time) forced her to choose between continuing their relationship  and carrying her baby to term. She chose her baby. During one therapy session, the therapist tells Tim that his habit of abandoning women stems from his father’s abandoning him, a hard truth which Tim embraces. On Day 28, Tim writes: “My grandparents have been together for 56 years. If there’s ever been hope for me to make a relationship work, it’s the standard that those two have set.”

In the end, Forty Days of Dating is no Jane Austen novel. After a weekend trip to Disney World, Tim and Jessie break up. At that point, Jessie is very invested, even though Tim doesn’t actually treat her that well. Tim decides he’s afraid of the commitment and of hurting her. “I thought of that Bob Dylan song where he says, ‘I gave her my heart but she wanted my soul.’ And I know that what I could offer right now would never be enough for someone like Jessie,” he writes in his final post.

The conclusion of Forty Days of Dating isn’t quite as depressing as the existence of the “Bang With Friends” app, but it’s still pretty disappointing. It’s yet another testament to the fact that relationships and family-formation have been so deconstructed that there’s no longer much of a trajectory to follow. Still, Tim writes: “My whole life has been turned inside out from this crazy experiment. I do want to be in a relationship. I do want something meaningful.”

And so in a very postmodern, very millennial viral blog that will either soon evanesce or, more likely, be turned into a second-rate rom-com, there’s a nugget of truth: Even in the era of modern love, people want to be known and loved, and to be part of something meaningful. They just don’t know how to get there any more.

— Madison V. Peace is assistant to the editor of National Review.


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