40 Days of Dating: First Comes Friendship, Then Comes…Dating? Katie Patton

This just in: dating is hard. Scratch that. Dating used to be hard; back when boy met girl and girl agreed to go steady. Yes, plain old going steady was still hard, without the help of technology, when it was still called going steady. Now we find ourselves immersed in 2013, a year in which dating is tougher than most Olympic sports and your ability to lock down plans with a sane prospect for Friday night should land you atop the medal podium; definite gold goes to those whose night doesn’t end resembling a scene from Girls. So, what are modern day guys and gals to do when the tweeting, texting, facebooking, online-dating world of present-day love has tired them out and let them down? Well, best friends Timothy Goodman and Jessica Walsh decided to date each other. Luckily for all of us, the duo documented the experiment every step of the way.

By now, you have probably heard of 40 Days of Dating. Envious observers have been posting their obsessions over the project via various forms of social media for weeks; friends wait anxiously for the previous day’s activity to form the present day’s post, leaving them to discuss the developments. The dating life of Tim and Jessica is consuming the happy hour conversations of both committed and single men and women all over the nation. If you have somehow escaped being sucked in to the latest internet craze, allow me bring you into the vortex with the rest of us.

Tim and Jessica, best friends living in New York City, found themselves single at the same time after seeing one another through years of crazy relationships and endless dating. Their single statuses wouldn’t last however, as they concocted a crazy, yet amazingly awesome, idea that would reveal if opposites really do attract. Walsh, a self-proclaimed hopeless romantic who is constantly searching for “the one” wondered if she was sabotaging her relationships by jumping in too quickly; or perhaps the guys she dated just sucked (sometimes, it is totally their fault, ladies.) Goodman’s situation was just the opposite; he was the one half of the friendship possessing a romantic history littered with often meaningless dating and, as stereotypes would have it, an evident fear of commitment. Owning up to their faults and realizing their vastly different outlooks on love, the long-time friends made the decision to pair up and explore their fears and inadequacies. Since it has been said it takes forty days to break a bad habit, Goodman and Walsh vowed to go through the motions of a real relationship for that exact amount of time in hopes of overcoming their dating downfalls. Thus, 40 Days of Dating was born and the millennial generation rejoiced.

The allotted forty days has come and gone for the friends turned couple and now the whole world gets to read about their trial period one day at a time. Currently over halfway through the unveiling, the website provides daily updates on the happenings and events of the couple’s dating life, as well as Tim and Jessica’s emotions and thoughts through graphic designs, original art, videos, photos and question and answer sessions. The rules their followers are eagerly observing them abide by seemed simple at the onset- see each other every day for forty days, go on at least three dates per week, see a couples therapist once a week, go on one weekend trip together, fill out the daily questionnaire and document everything and, lastly, not see, date, hookup or have sex with anyone else. On second thought, how simple would it actually prove to be? Would their dating ruin their friendship? What if they hooked up? Would it be awkward after? Would they end up together? All questions they asked themselves when they dove in head first; all things we are learning one day at a time.

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  1. I haven’t heard about this until I read it here. I myself have had the friendship move to dating and it always ended up badly. Plus, you can lose a good friend in the process. I would like to believe it is better to be friends first than to just find someone out of the blue, but for me, it hasn’t happened yet. I believe in love and friendship, so where is it?

  2. After this article I had to play catch up, as this was the first I heard of it. Now it is an enjoyment to wake up and refresh the website until the new post is there! It is nice to have a story to wake up to that has ups and downs, but ultimately an optimistic goal, rather than jumping to a news site spreading fear and pessimism. I haven’t found something as entertaining to read since a past blog called “Goldie the Goldfish”, which had a similar basis in finding love, but revolved around a girl’s adventures with online dating. Much in the same way, she set rules for herself which most of us would not follow in our own dating lives which made it interesting. Anyway, I will truly be sad when it ends! 40 days is just not enough!

  3. I came across this around day 5 of their posts. I’ve been obsessed as well! Checking for updates first thing in the morning so I can see what happened between the two of them that day. I relate a lot to how Jess is in her relationships so hearing Tim’s view on her tendencies really helps me to understand how I might come off in relationships. It also gives me an entirely ne perspective to one of my friends who is a lot like Tim. This opened me to a whole new way of viewing things, people and myself. Love this story! I’ll be bummed when we get to day 40 and it’s all over.

    • I am too, Nicole…completely obsessed! My best friend and I both read it every day. I think it is like you said, I am similar to Jessie as well so every time I read her recap and then Tim’s I learn a little something. Definitely interesting and entertaining…I don’t want the 40 days to end either!

  4. I have become obsessed with the project. I love how cute they are. I love how on opposite pages they can be. I love how I notice similarities in Tim within myself and how following his adventure is helping me discover new things within myself.

    • I love how opposite they are too, Justine! It is sort of what makes their relationship tick. I notice similarities in myself and Jessie, so reading Tim’s insights has definitely made me think about a few things!

  5. Yay! I’m rooting for them! I feel like friendship then dating is the best route. Love in relationships isn’t about striving to be completely compatible, have ooey-gooey feelings all the time and great sex. It’s about vulnerably loving one another, which leads to self-transformation in the other and especially yourself. In other words, helping the other become a better person while understanding we must be willing to change as well. I hope that if our culture would have a reality check on relationships we would see less broken families.

    • I am rooting for them too, Lily! I also think they are learning some of points that you touch on in your comment during this experiment, which is very interesting…maybe we all need to learn those things…

  6. I love this! I can’t wait to see how it turns out. It’s so great to get a little insight into what the “other half” is thinking in these dating situations I’m sure we can all relate to.

  7. I feel like dating someone you’ve had a solid friendship with sometimes turns into a disaster. That being said, my boyfriend and I have been friends for 5 years. And when my last relationship ended badly he gave me the time I needed to rebound and then chivalrously stepped up to the plate to tell me he has been interested in me for most of those years and he wanted to take me on a date. Without ties, I accepted and we’ve been dating ever since, 8 months now. I’ve never been happier. It makes me love him more, knowing him the way I did. I think they’re on to something!

    • He sounds like a catch, Stephanie! I am so happy it worked out for the two of you and wish you continued success with the relationship! Maybe it will be the same for Jessie and Tim!

  8. i am so psyched about this project, i cant wait to see how it ends :)

  9. I am surprised HelloGiggles is now just writing about this. It is truly fascinating. My friends and are saying it the romantic comedy you want to watch. Jessie and Tim are fascinating. It is worth the read. Whether or not they will together after the experiment is done is a different story. But they have ten days left so we will just have to see,

    • Hi Rachel! I have actually been following it and preparing the article for a couple weeks- I just got so caught up in seeing what would happen with them everyday! It really is like reality dating but, actually REAL! I sort of hope they end up together, but also am not sure if I think they are right for each other…I guess we will see very soon! Thanks for reading!

  10. I’m intrigued! Heading over now to play catch up.