I’m Totally Obsessed With This “40 Days Of Dating” Project

How can we be lovers if we can't be friends?

Jessica Walsh is a mega-respected NYC creative who considers herself a hopeless romantic who really wants a boyfriend. Timothy Goodman is a self-employed designer and a self-professed commitment-phobe, who likes dating a lot of women at the same time. The two are friends who happened to find themselves single at the same time, so they embarked on a pretty crazy experiment: Date. For 40 days. And see what happens. The pair wanted to explore their own emotional issues and test the boundaries of their relationship. Could they grow and develop by dating one another? What sort of emotional changes might the relationship yield? And would this crash and burn in their faces big time?

As any woman in her 20s or 30s in NYC can tell you, dating sucks here. Dudes are always on the come up for someone better looking or more interesting — a head-swiveling habit Tim readily admits to. Jessica, on the other hand, cops to a familiar lady trope: Willing to overlook the untenable in someone in order to make a relationship work. The pair embarked on the 40 days of dating armed with couples therapy sessions and a healthy dose of nerves. They’re currently only about half way through the project and just hit a major milestone — a major makeout sesh, but no sex.

Reading back through their daily journal entries about the experiment, a pattern emerges: Jessica wants their situation clarified, discussed, solidified. Tim can’t handle the pressure. The push-pull is making them both unhappy because Jessica’s already developed expectations, which makes commitment-phobe Tim really nervous and uncomfortable. Witness Tim’s entry from day 14:

We talked about our “relationship,” but everything about our conversation felt so heavy. It was full of innuendos and cryptic bullshit. I felt like we just needed to be more honest with each other. I took out my notebook, ripped out a couple sheets of paper, and I suggested that we write “pros” and “cons” about this project/relationship. It’s always easier to be honest on paper, but I don’t think this really changed anything.

And here’s Jessica’s M.O., from day two of the experiment:

I am extremely picky about who I date. However, when I do decide I really like someone, I am quick to jump into a relationship in order to test it out and see how it goes. I become extremely invested in people and things that I care about, which can cause me to fall for someone quickly. Tim thinks I should be more cautious…

Will this work out? Will it blow up in their faces? We’re 18 days in (though they actually completed the entire 40 days of dating a couple months ago, they’re only now revealing the documentation from that time), and only time will tell. [40 Days Of Dating]

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