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This Date Taught Me to Embrace Spontaneity

“I want to take you on a penny date,” he told me, already confident that I would say yes. I responded with a curious but confused facial expression, wondering if I should offer to help pay.

“On a penny date,” he continued, “you have no idea where you will end up, you just get in the car and flip a coin to guide you.” I let my eyebrows dart up toward my hairline in what I hoped was a pleasantly surprised expression. Well this keeps getting better and better, I thought to myself, a man without a plan… every woman’s dream.

In a world starved of spontaneity, the prospect of wandering around without a known destination—let alone dinner reservations—can be rather irksome. Like so many other women, I desire the unexpected but balk at the prospect of things unplanned.

But my date did have a plan of sorts. That is, his plan was to have no plan. You see, the allure of the penny date is the unexpected. You call a number between 1 and 30 and then set out in any direction with a penny and your date. When you come to a red light, stop sign, or fork in the road, you flip the coin—heads means go right, tails go left. You stop when you have flipped your penny the predetermined amount of times (in my case, 30). You stop wherever you are and have your date.

At first I was thrilled at the prospect of the proposed adventure. I immediately began imagining the perfect spontaneous date. A vision involving the discovery of a scenic overlook and a bottle of wine began to take shape, and then anxiety began to creep in. What if we drive around in circles? What if we end up in someone’s front yard? What if there are no scenic overlooks? What if things don’t turn out the way I had envisioned?

Like many women in their 20s and 30s, I’m accustomed to living life according to plan. Most of us have the freedom to arrange our lives just so and there isn’t much we let get in our way—even our natural fertility cycle must become subject to our dictation. But when it comes to love, I have noticed that our precious plan almost always gets thrown in the chipper.

So it should come as no surprise that our penny date did not lead us to the scenic overlook I had dreamt up. It led us in circles mostly, then around a strip mall parking lot, down neighborhoods of condos, and then back in the other direction again. At 7 p.m. it was dark outside and every flip of the coin ended in a frantic search for the lost penny on the ground of the passenger seat. With every left turn and right turn, we both got hungrier and then hangrier.

This was not the adventure I had in mind. The timing, the backtracking and circling around, and the likely destination (7-Eleven, anyone?) was not my ideal romantic adventure. Still, at some point in between our comically loud stomach growls and my twentieth attempt to recover the penny in the dark from somewhere between my legs, I managed to let go of my plans and have a wonderful time. The date was a comedy of errors to be sure, but instead of rejecting the reality of the situation before me—that this was not what I had envisioned and yet still pretty wonderful—I found that I was perfectly satisfied. We laughed at the situation we found ourselves in and we even cheated a little bit—yes, I know the rules say turn when you flip the coin, but we were not about to get trapped in another parking lot.

On this date I got a glimpse at how incredibly liberating it is to realize that your plan might not actually be the only road to happiness, especially when it comes to dating. A plan offers a course of action, a sense of security in a world of so many variables—it’s a form of positive juju. “If I will it to be true, then it will be” and, dangnabbit, we like having a plan! But as my mother always reminds me, “You can plan yourself out of a lot of happiness.”

Whether it’s the fear of meeting someone online or falling in love with someone who doesn’t fit our profile, we sometimes hold on to our ideals too tightly. I think where our plan leads us astray is when it begins to more closely resemble a script than a course of action. Too often we begin to memorize this script so thoroughly that we rule out any chance for improvisation. It seems to me, that the more entrenched we are in our own plan, the more the fear of any alterations consumes our desire for authentic happiness.

As we set out on our dates or scroll through yet another online dating profile, try taking a breath and imagining a story other than the one that has been crafted in your head. So what if the timing is off or the man of your dreams does not look anything like the man you always dreamt of? This is what the really good love stories are made of.

Who knows, you just might find yourself, perched on a bar stool 30 flips of a penny away from your house, with his coat wrapped around your shoulders thinking, well, this isn’t so bad.