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'40 Days of Dating' teaches nothing about relationships and everything about hipster New York

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Are you ready to be hurt? What happens if you screw up your friendship? And on and on and on!

Jessica Walsh - Like Knows Like

I almost had a panic attack. However, neither Jessie or I would have talked about this stuff so soon without having the therapist as a soundboard. I think it was helpful. But I do save money, while I think she spends. I get uncomfortable talking about what could happen in the next 40 days. I was sort of freaking out after therapy. I was texting with one of my best friends, Greg in Chicago, and he told me to just have fun with it. So, I want to make sure I just have fun with it.

Jessica Walsh

Are we afraid to go after what we really deserve? The play is about a bunch of college students going to parties, getting drunk, having sex, and their complicated interpersonal relationships. The characters are either opportunistic, self-serving, entitled, indulgent, or power-seeking. I found the complicated dynamic of these different personalities to be an interesting twist on the usual character development. After the play, we wandered over to a bar nearby in the West Village for a drink.

Tim told me about his last serious relationship with a girl he dated in San Francisco when he worked for Apple. I feel like he broke her heart.

40 Days of Dating: what happened next? | Creative Bloq

Things were getting serious between them when she had to leave for business for a few months. The long distance scared him, and he broke off the relationship when she got back. He seemed to feel bad about it. One part of the play stirred up emotions from something that happened in my past.


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  • I was slightly shaken up after the play so I told Tim about it to explain why I was acting strangely. I try not to look back too much and get caught up in the past, but sometimes it does unexpectedly creep back up on me. It was cute that Tim insisted on being a gentleman and walking me home after the play.

    I am a sucker for the common dating courtesies. Tim seemed slightly annoyed that I missed his text messages before the play. I hate text messaging.


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    My fingers get tired. The misunderstanding and the AutoCorrect drive me nuts. When I have a crazy day at work, I often forget to check my cell phone. I know this drives certain people a little crazy.

    Timothy Goodman

    I guess I should look into an app that downloads texts to the computer. I just wanted to stay in and watch the Knicks game. However, Jessie and I have something planned on Sunday, so it was probably best to do a date tonight instead of Saturday night. Anyway, we went to the Off-Broadway play, Really, Really. We went out for a drink after the play.

    When someone does that, your natural inclination is to tell them something extremely private back. The duo, who have been friends for four years, decided to embark on a relationship "experiment" after finding themselves single at the same time. They settled on a day timeline, and agreed on six rules: In an attempt to explore and hopefully overcome their fears and inadequacies, Tim and Jessica will go through the motions of a relationship for the next 40 days: Can they help each other, or will they fall into their same habits?

    Will they damage their friendship?