Why I Stopped Waiting for Love to Happen to Me

I am not a rash woman. I make careful, thoughtful decisions. I’m a “why?” person; I won’t really do something unless there’s a specific purpose for it. My friend Jordan used to describe me as “calculated” to random people — which was only mildly insulting because, despite the negative connotations surrounding the word, she was kind of right.

In the giant chess board that is my life, I move pieces with deep consideration and forethought. So when I blew off my family Thanksgiving and hopped in a car to Chicago to crash the birthday party of my crush — a friend of my friends — people were confused.

I had no game plan. It was a last-minute call. He had no idea I was coming, or that I even liked him beyond our mutual friend’s passing mention that he should make a move over the summer while he visited. (He did not.) I knew my friend’s nudge had probably been long-forgotten, and I knew it was possible he wouldn’t return my interest, but I decided to ignore my doubts, fears and shyness, and go to Chicago anyway.

But sometimes all you need is a few stars to align, a bit of intrigue, and a dash of confidence.

His lack of knowledge about my interest wasn’t the only barrier to starting a relationship either; he lives in San Francisco, I live in Ann Arbor, Michigan. But sometimes all you need is a few stars to align, a bit of intrigue, and a dash of confidence. When he heard about my whirlwind attempt to catch up with him on his birthday, he asked me out on an official date the next night. My adrenaline was still pumping the next morning during our first real moments alone together, on the couch of our friends’ large Chicago Airbnb, just hours before I had to head back home on a train.

“Why?” he asked me, with a sort of confused laugh, partly pleased and partly skeptical. In a culture where we hide behind screens and romantic intentionality is somewhat of a fading relic, I said the only thing I could think to say: “I just had a gut feeling about you.”

The decision to go to Chicago may have seemed rash on the surface, or out of character to everyone who knows me, but it felt perfectly purposeful to me. That’s because when it comes to love, maybe love or potential love, I’d already decided no risk is too big.

Despite living thousands of miles apart, we’ve talked and texted every day since. We’ve endured three cross-country trips between the two of us, despite chaotic job schedules. The odds are stacked against us, but I haven’t been more excited or hopeful about someone in a long time.

If you want to call this interpersonal commingling we now do “dating” — you have to get comfortable with improbability.

If you take each individual connection in a vacuum, the chances you’ll fall together and not apart are low. But after talking to many modern couples over the past several years, I’ve discovered a few foundational principles that increase your odds. There’s one in particular I want to share with you today, the very one that caused me to climb into that car back in November: To date today — if you want to call this interpersonal commingling we now do “dating” — you have to get comfortable with improbability. All love is improbable, and the strongest relationships are built on the strongest connections, no matter the variables involved.

In researching my book on relationships, I listened to a lot of great love stories. On the surface, I can’t think of many I’d call “probable.” Some of my favorites, off the top of my head? One, a couple who was broken up for five years before they both mutually realized they were absolutely right for each other. Two, a husband who told his now-wife he’d help find her a great boyfriend when she was finally ready to date again after a horrible split from her ex. Three, a long-term couple who began dating just two days after he filed for divorce. Four, partners who met in kindergarten and married in their thirties. Five, a pair who talked for nine months cross-country before taking a big ol’ leap to live together in the same city; they have two kids now.

Maybe that last one inspired my current situation, although I suspect the whole concept of “improbable” did one better; after many diligent months of research, I internalized that modern love is just that. Even when I think about youngish committed couples in my own social circle, few have a straightforward romantic trajectory — despite how, growing up, my mom used to repeat refrains like, “when you know you know,” “or, “when it’s right, it’ll be easy.” Oh, how the world and relationships have changed.

I think about love’s improbability a lot. We are wired to sample the field and delay commitment until we’re “ready,” or feel certain we know what we want, testing different types of connection in a vast sea of potential matches via Tinder, friends, bars, work, hobbies, and on and on. It’s the millennial dating version of optimal stopping theory, where you need to figure out when and for whom to take yourself off the market, except that the sample of suitors is virtually unlimited. Only you decide when you want to stop, or what’s worth investing in, as you determine what you want, need and are looking for in a partner.

Purely rational relationships with great-on-paper types don’t leave room for the highly irrational process of chemistry and connection.

But unless you are in a wonderful headspace to build a healthy relationship and meet a someone else who is in an equally commitment-ready state of mind, you might end up with a missed connection. The odds are stacked against us because, in addition to testing the field, we are a generation constantly in motion; we travel, we prioritize friends, we change jobs, we pursue degrees, we want to chase dreams and find fulfillment. Connections can seem fleeting; we’re not always looking, we’re coming off heartbreak, we’re still working through family baggage, we’re living a country apart from our love interest, work is crazy, etc, etc.

Where does love fit in? Again, only you decide when, with whom and how to invest an improbable landscape. Welcome to millennial adulthood.

The variables are such a mess, the romantic era we’ve inherited can feel hopeless. I’ve certainly cried about the apps, vented to my girlfriends about the ghosting, toasted all the bad days and broken hearts. But all the while, the improbability makes me sure of at least one thing: I’ll be braver when I encounter a potential connection.

Bravery, in the midst of improbability, is yet another hallmark of many modern-day loves. I had this conversation over the course of months with a good friend of mine, who waited a full year for her guy to finally commit again after his divorce. She was bold in her feelings, strong in her conviction that he was worthwhile, and steadfast in her patience with his timeline. “Everyone told me to let him go,” she said of her friends, who were playing the odds without knowing the connection. She didn’t let him go; she’s so glad.

If you’re like the vast majority of people looking for a single long-term love someday, connections that may lead to lasting relationships don’t come around often. The way I’ve decided to increase my odds is simple: Be brave in my feelings, bold in my risks, and cognizant of those strong connections. If I’m open and sure of what I feel, I can rest assured that I’ve given a connection a fair shot.

My goal is to ultimately end up with one person. As such, I’m not getting tangled in the logistics of this guy in San Francisco, wondering how it can all work out right now. Purely rational relationships with great-on-paper types don’t leave room for the highly irrational process of chemistry and connection. That is the glue in between, the reaction that forges a bond, the little spark of (necessary) madness.

Such inexplicable elements of modern love give this calculated woman hope, allowing me to make crazy decisions that just feel right. Is my current long-distance connection improbable? Sure. More improbable than my next online date? I’ll let you decide; I already know what I believe.

Collage by Louisiana Mei Gelpi.

Jenna Birch

Journalist, dating coach and author of The Love Gap.

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