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).