What The “40 Days Of Dating” Website Says About Relationships

I open my eyes, my body’s first stirring of the morning, shaking the faint heaviness beneath my eyes. I roll over. He’s there. I look beyond him, focusing on the window of his room. The curtains are drawn slightly, the silhouette of an evergreen tree just in view. The sun lingers just behind it, slowly creeping up, leaking light through its needles. I check my phone. It’s about that time. I squeeze his shoulder. His head turns. His eyes flutter, grasping to comprehend my words. “I’ve gotta go.” His eyes widen. They’re earnest. He’s still drunk. “Don’t.” He rolls toward me, wraps his arm around my waist. These are the moments I cling to. Five minutes later, we’re at the front door, disheveled, maybe still dreaming. He kisses my forehead, and I’m gone.

“It’s not going to hurt me,” I’m explaining to a friend on the phone five minutes later, driving toward the highway. “It’s simpler this way.” I don’t know the next time I’ll see him, and I don’t care. Knowing that he’s here whenever I return, that’s enough. I don’t want to text him. I don’t want to FaceTime every night. But when I’m around, and he’s around, he’ll hold my hand as we cross the street. I’ll fall asleep on his shoulder. He’ll kiss my forehead. He’ll tell me he wishes we could see each other more often, but we both know that’s not true. This is the best way.

A few weeks ago, I stumbled across a website called 40 Days of Dating. It follows two close friends in New York who decided to date each other for 40 days when they were both dissatisfied with their love lives. Jessica jumps into relationships too quickly, and Timothy can’t get serious with a girl. They set specific rules for the experiment, and each of them wrote about the experiences daily. Months after it ended, they published these journal entries, one per day, for 40 days. I stumbled across the site on day 38. By day 39, I was caught up and ready for the reveal of day 40 (did they end up together or not?) along with everyone else who had been following along. The site became a phenomenon of sorts. Just a few weeks after their last post, Jessica and Timothy have signed with CAA and inked a deal for a film adaptation of their experiment.

There’s something relatable here, addictive even. I found myself intrigued, scanning back and forth between Jessica and Timothy’s journal entries, seeing how they as individuals documented the same days from unique perspectives. Maybe it says a lot about men and women, or maybe their different personalities, or maybe just them, or maybe humanity in general.

On the Friday morning the 40th post went live, I refreshed the website multiple times, waiting for it to appear. Day 39 had not ended on the most positive note. I didn’t expect a last minute 180 degree turn, Hollywood style. I never even wished for it, but I did want to see how they wrapped it up. After 40 days of dates, conversations, misunderstandings, flirting, couples counseling, fights, and sex, how would these two friends come to terms with the fact that it was over? I felt like I’d been on an emotional roller coaster with them, picking their brains each step of the way, and I wanted closure.

In the last moments of day 40, Jessica and Timothy shared a cab home. Jessica wrote, “And as if we were in some sort of twisted fairytale, he left me at the stroke of midnight with the gift and a goodbye kiss.” This couldn’t have been what they expected, this strange in between, this endearing sort of pain, the kind that strings together entrancing, beautiful words even as they sting. Timothy’s final words: “I just can’t believe it’s over. I feel so close to her. I know now that I’m in love with her. I love her, yet I know there’s nothing else I can do. We kissed. I gave her a gift. We kissed one more time. I shut the cab door, and I walked away.” And there it was again, the gorgeous sadness. The truly bittersweet ending.

Their story has all the makings of a typical rom-com, the sensitive girl and the emotionally detached guy, the idyllic Manhattan backdrop, yet Timothy’s last words haunt me like no Meg Ryan movie ever could. The irony of it is poetic; he loved her, and it took ending things to realize that. And this is day 40. There’s no additional scene, running through pouring down rain to proclaim this newly realized love. He realized it not just when it was over, but because it was over, really over. This is modern love, I thought. The gray areas. The complexity of relationships. Nothing fits into a Matthew McConaughey and Kate Hudson shaped box anymore.

But something about these words lingered. They stuck with me for weeks. They’re new, but they’re familiar. I hang up the phone call with my friend, cruise control now set, mile markers flying by. There’s no use explaining this relationship, fling, friendship, arrangement, or whatever. It might not make sense. But that’s okay.

Or is it? Maybe this pain is inevitable, somewhere down the line. What we don’t know about Timothy and Jessica was how hard it was for them on day 41, or 42, or 59, or now. And as thrilling as it is for us to peek into the bits of their souls they put on the Internet, the pain was real for them. Is it worth it for the beauty, for the story? I take a deep breath. Before I know it, I’ll see the familiar palm trees, not evergreens, rolling by me on the highway. It’s back to the routine. I roll down the windows and crank up the volume on my car stereo. I press play. Books on tape. It’s what I always drive with. Just a little bit left of The Great Gatsby. Jake Gyllenhaal’s voice soothes me down the highway. It picks up as Nick says his final goodbye to Jordan. “Angry, and half in love with her, and tremendously sorry, I turned away.”

This isn’t modern love. It’s just love. We swear up and down that love is changing. Divorce rates are going up. Relationships are harder to define. Nothing is conventional anymore. But we don’t know what went on behind closed doors in the past. Perhaps the saddest love stories belong to men and women caught in marriages they were afraid to leave. Love’s not changing. Society is. Love has always been messy, and that’s not going away anytime soon.

My phone buzzes as Jake Gyllenhaal utters the final words of the ninth chapter of The Great Gatsby. I pick the phone up. It’s a text from him. That’s odd…but sweet. My mind races. Maybe he wants to tell me he had a good time. Maybe it would be nice to chat even when I’m not in town. Maybe there is something there. I open his message. “think u left ur lipstick here… def not mine, haha.” I put my phone back in my lap. A few hours later, I stop for gas and remember to reply. “Thanks. I’ll pick it up next time, sometime, whenever that may be.” I pause before sending. I add a “haha” at the end, you know, for good measure. TC mark

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