40 Days of Dating

I know I promised lots of life updates coming up here, but in between the last two nights of "Bachelor in Paradise" (#TeamKristina) and a few hectic days at work, I haven't felt like taking the time to do justice to my life lately. Instead, I revisited an old favorite, and wanted to share it. 

Have you guys heard of 40 Days of Dating? It's a social experiment-slash-blog written in 2013 by two graphic designers, Jessica Walsh and Timothy Goodman, about how they dated for 40 days to try to overcome their respective relationship issues. Jessica falls too hard, too fast, and always for the wrong men. Tim, on the other hand, is a classic serial dater and commitment-phobe. Their daily dates, including couples therapy, a weekend trip to Disneyworld, and plenty of ups and downs along the way, charmed me the minute I discovered it in 2013, around day 18's publication.

I read breathlessly along the first time through, convinced they were going to end up together. (Spoiler alert: they don't. Jessica is happily married to someone else now - see their wedding here. BOOOO.) That said, they are both incredibly candid and vulnerable throughout the series, and being able to read their respective thoughts and intentions, along with how the other perceived them, was a fascinating dive into human experience. 


I remember re-reading the series probably two years ago, and stumbled back on it yesterday to marathon through it again. Some of the things that stuck out most to me now are that I'm officially older than they were when they did the experiment in the first place...a weird and kind of unsettling feeling, given their respective focus and obsession with dating. I'm just kind of...not, and that makes me feel like I'm doing things wrong. 

Second, this section on online dating, from a portion of Jessica's Day Nine entry: 

"We no longer search for romantic partners, we shop for them. Just like when looking online for a new pair of shoes, one can sort men by highest rated, size, popularity, even by color. While I admit it’s all very practical, I have to wonder if it’s caused me to miss out on spontaneous interactions or chance encounters."


You guys, it seriously messed with my head a little bit. I HATE online dating. As I've chronicled numerous times, I'm utterly terrible at it, and it always comes to feel a little dirty and cheap to me. This, I think is why - I am a consummate consumer, but the act of searching for a partner the way I search for a deal at J.Crew is repellent to me. 

Third, I really love and identify with their Day Five activity of illustrating their past relationships. See art (and ones I especially identify with) below: 

It all made me wonder if certain tropes and kinds of hindsight have a certain universality to them - if everyone has a person who was too good to them, or, conversely, has someone to whom they regret being too good. If there's always "that guy from New Years" or something. 

Finally, I love the stark, bold, graphic nature of the site. Tim and Jessie visually curated their way through their 40 days, with hand-drawn art, snippets of iPhone messages and chats, and photos of souvenirs, tickets, and ephemera. The way the art came together created a powerful third character in their relationship - how they both distilled and perceived their relationship, and expressed it together. 

Tim and Jessica released an "extended cut," of sorts, in the form of a book in 2015. I'm tempted to pick it up and read it, and to see how much extra info they popped in there - who knows? That said, if you've got a spare few hours and a desire to play fly-on-the-wall in another pair's relationship, it's super interesting. The added element of self-awareness, knowing this was an experiment with a fixed end date, just added to the tension and self-examination present throughout. 

They've done another project, 12 Kinds of Kindness, and I think you can all probably guess what I'll be reading later on tonight!