Here’s What Happens When Two Friends Agree To Date Each Other For 40 Days

Many, many relationships begin as friendships. A suggestive look or touch or — we're all adults here — one alcohol-fueled evening can trigger that tidal shift from "just friends" to "together." Few friendships-turned-relationships begin as deliberately as Jessica and Timothy's, though. Frustrated with the New York City dating scene and tired of complaining to one another about their failed relationships, the platonic pair wondered: What would happen if they dated each other for 40 days — and strove to break their worst relationship habits in the process?

A self-described "hopeless romantic," Jessica would hurl herself into every new fling, only to be crushed when it didn't work out. Tim, meanwhile, preferred juggling women to looking for "the one," and admitted he was worried about his inability to commit. "I think this project is crazy and wonderful and risky," he stated, "and Jessie is the only person I know who’s as crazy and risky." "Tim and I have been friends for years, and we always make fun of each other about our relationship problems," Jessica explained at the beginning of the experiment. "I wonder if putting two people together with opposite issues could help."

The rules of engagement: Jessica and Timothy had to see each other every day, see a couples' therapist once a week, complete a daily questionnaire about their progress, go on at least three dates a week, and go on a weekend trip together. Oh, and they couldn't "see, date, hook up, or have sex with" anyone else. When two friends decide to create romance from scratch and document the details, you expect a fascinating sociological roller-coaster ride; when those friends are both designers, illustrators, and art directors, what you get is also a stunning viral blog and then a graphic, full-color book chronicling their experience. 40 Days of Dating: An Experiment is out today. Read on for excerpts and a sampling of the book's art.

Day 1: March 20, 2013
Jessica
"We had our first date at the Fat Radish on the Lower East Side. They have the best roasted carrots... Truthfully, I am quite nervous. However, I know that when an opportunity scares me, I must go for it. I don't like having fears. No matter what the outcome, it will certainly be an interesting experience."

Timothy
"The new Justin Timberlake album came out yesterday and it's totally got me in the mood...but really, Jessica and I should share a 'JT' logo with him. Anyway, I feel like there was definitely a moment last night when we both said to ourselves, 'Damn, are we actually doing this?!'"

Day 21: April 9, 2013
Jessica
"Tim thinks I fall within the 'good girl' role and that I should channel my masculine energy a little more... He thinks I am too forgiving and empathetic, and that I've let friends or past lovers take advantage of this. I like to make people that I'm close to comfortable and happy."

Timothy
"It's easy for me to compartmentalize the things in my life, and not let my 'worlds collide' like that old Seinfeld episode... I can already see how I'm putting Jessie in a little box, not letting her touch the rest of my life. I know this isn't healthy. I'd like to change it, but I'm not sure how to really do that right now."

Day 39: April 27, 2013
Jessica
"I already loved him as a friend. After I allowed myself to open up to him and let my guard down, I've started to fall for him romantically. It seems I've repeated the same pattern again. I opened up too quickly, empathized too deeply, and I have another failed relationship to add to the list. I don't know what to do or think at all anymore."

Timothy
"We got back and sat in bed together. As we sat there, we started rubbing each other and kissing. I can honestly say I've never been more aroused in my life than I was at that moment. I wanted every single part of her, but there was so much guilt. She whispered, 'Should we have breakup sex?'"

Snag a copy of the book to get the full story of Jessica and Timothy's experiment — and find out how it ends.