The Story of Jessie and Tim: Trials (and Some Triumphs) for Two Dating Friends

Jessie and Tim were best buds who tried an experiment: date for 40 days to see if they could hack it as a couple. Here's what happened...

Jessica claimed she fell in love too easily. Tim feared commitment. When the two friends found themselves single at the same time, they decided to start dating so they could work their relationships out…on each other. Kind of like being each other’s starter wives?

They dubbed the experiment, “The 40 Days of Dating” and they documented every step and every day on their blog. They had six rules: that they would see each other every day, go on at least three dates a week, see a couples therapist once a week, go on at least one weekend trip together, document everything, and swear not to date, hookup or have sex with anyone else.

Easy enough, right? Not so much. During the length of the forty days, both of them actually quit the experiment once, but were talked back into it by the other. And on the 40th day, they broke it off for good.

It was a noble experiment. You could tell they actually tried. Well, at least Jessica really did (totally siding with the girl here). There were a few times when you thought that they might actually make it -- there was no doubt that they had fallen for each other. But the pretense of an experiment -- and even a therapist -- did nothing to prevent them from falling into the same problematic patterns they fell into in past relationships. Every day, they answered questionnaires about how they felt about themselves, each other and their relationship, and that led to some serious discoveries. But at the end, neither of them were really sure if their problems were fixed.

“This was like boot camp, and we learned stuff about each other that one wouldn’t normally know for a long time. Maybe we should have seen this coming the whole time. While I feel exhausted from it all right now, I also feel a real sense of hope for myself. This has completely challenged my personal life, the way I conduct myself, the way I approach relationships, how I consider the consequences of my actions, and my ability to let a woman into my life emotionally,” wrote Tim on the last day.

Timothy and Jessica call the experiment a success because they feel like their problems are the same as a lot of other people’s and hopefully this gave them something to relate, too. We, on the other hand, don’t know if you can call something a success when you feel like this:

“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,” wrote Jessica on Day 39.

Whatever you might think, there are already rumors that Hollywood’s come a knocking. Perhaps that story will have a happy ending.

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