Hear horrific dating tales from the 40 Days of Dating bloggers

New Yorkers Jessica Walsh and Timothy Goodman of the experimental dating project–blog recall their worst tryst ever.

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Have you started reading 40 Days of Dating? We promise it's your next blog obsession (other than the TONY blog, of course). It chronicles the weirdly entertaining experiment of New York graphic designers Timothy Goodman and Jessica Walsh, two friends who found themselves simultaneously single and decided to start dating for the titular amount of time.


Goodman and Walsh update the beautifully rendered blog on a daily basis for a slow, addictive unfolding. During the experiment, which was actually conducted this spring, they committed to see each other every day, go to couples therapy once a week, and not date or hook up with anyone else. (For more on the rules, see the below video.)


Reading their daily accounts side by side is enlightening, captivating, slightly voyeuristic and sometimes amusing (there are some classic men-are-from-Mars-etc. miscommunications). Have you ever dated—or thought about dating—a friend? Are you rooting for Goodman and Walsh to work out as a couple? How do you think the whole shebang will end? Let us know in the comments.


  • Photograph: Santiago Carrasquilla

    We got an exclusive scoop: Seasoned daters Timothy Goodman, a self-declared commitment-phobe, and Jessica Walsh, a relationshipist prone to falling fast and hard, tell us about their worst rendezvous ever. Oddly enough, both responses—which were sent separately—happened at LES eatery Freemans... Make of that what you will.

  • Jessica Walsh

    The worst date I've ever had was at Freemans. The food is amazing, but there is always a one-to-two hour wait. By the time we sat down to eat, I had detailed accounts of every past relationship he's ever had. He spent dinner talking about how amazing and successful he was, how lucky I'd be to date him, and what an amazing boyfriend he'd be to me! He barely let me get one word in the whole dinner. He ordered an enormous amount of food, and I only had an appetizer as my stomach was in knots. When it came time to pay, he fumbled around in his pockets, he forgot his wallet! I had to pay the $250 bill.

    Jessica Walsh
  • Timothy Goodman

    One time I went out with a girl who was just an absolute bore. We were at Freemans in the Lower East Side. Either my breath smelled that night, or hers did, because she was not interested in speaking. I was searching for any topic to talk about: work, family, friends, movies, books, music, politics, food, clothes, technology, religion, horoscopes, zoo animals, aliens, melted plastic, you name it. I wanted to die. Later, my friend had an interesting proposition: I should have pulled out a gun and shot myself right at the dinner table, then maybe she'd have something to talk about at her next date.

    Timothy Goodman

Photograph: Santiago Carrasquilla

We got an exclusive scoop: Seasoned daters Timothy Goodman, a self-declared commitment-phobe, and Jessica Walsh, a relationshipist prone to falling fast and hard, tell us about their worst rendezvous ever. Oddly enough, both responses—which were sent separately—happened at LES eatery Freemans... Make of that what you will.


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Editor: Marley Lynch (@marleyasinbob)

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