A version of this blog post originally appeared on RoleReboot.org, May 4, 2017. Read it on the website here.

DC woman taking risks while dating

I’ve never been a risk taker.

Jumping out of airplanes and popping pills never seemed thrilling or fun. It just seemed senseless and scary.

While this outlook has probably kept me alive and un-addicted to drugs, it has been less of a positive for my love life.

I wait for men to approach me. I laugh off offers from family friends to set me up. I avoid dating apps because I just assume whoever I’m meant to be with isn’t on one.

I’m careful, cautious, shamefully passive.

But this kind of close-minded, reserved approach has done little to help me achieve my longterm goals of finding a partner and starting a family. So, a few months ago, as I neared my thirties, I decided to throw caution to the wind, accept an out-of-the-blue invitation to (s)explore Detroit for a weekend with a chiseled watersports instructor, and just not think about the consequences.

To say this spontaneity nearly gave my mother a heart attack would be an understatement.

“You’re where?” she screeched when I called her from the DTW runway to tell her my whereabouts.

“Ummmm, did you know the flight from DC to Detroit is less than 50 minutes?” I offered.

There was a lot of sighing and words of concern from her end. I sat silently, waiting for the tirade to taper off.

“Make good choices,” she chided me before hanging up.

Seemed a little late for that.

But, no matter. I was excited! This was wild! No one could accuse me of playing it safe anymore!

I figured the odds of me being murdered were on the low end.

The guy I’d randomly decided to visit was working for the Hillary campaign (I mean, how many ax murderers were on THAT side of the election, really?) and had an active Instagram account overflowing with groups of friends engaged in healthy outdoor activities. Come on, do serial killers rock climb?

Even so, I was on the lookout for red flags.

“If you see ANY taxidermied animals in his room,” my best friend Julia warned me as I booked my flight, “turn around and walk out the door.”

I laughed.

“I’m NOT kidding,” she replied bossily. “You get the hell out.”

Suffice to say, he was not an ax murderer and I survived a weekend in motor city with life and limb intact.

I returned to DC gushing.

“He’s amazzzzzing,” I told my friends.

“I’m in love!” I sang to my sister.

“He’s different,” I swore to my mother.

I was convinced that by taking a leap so out of character — so spontaneous and unexpected — I had changed the very trajectory of my love life.

This was IT.

It had to be. Because the OLD me would never have done such a thing and that version of me was unlucky in love. This new behavior must signal something else. My luck would turn. Things were about to change. He was The One.


Of course not.

While my approach to dating has been considerably more broad-minded over the last few months, surprise surprise, Mr. Watersports turned out not to be the love of my life.

After the election, his grand return from Detroit was a reminder that he was, in fact, just a typical DC dude. Within a week, his true self became depressingly apparent: self absorbed, politically ambitious, constantly networking.  The muscled kayaker with a zest for life was suffocated under the suit and tie and Warby Parker lenses.

But it’s all for the best.

It might not have worked out between us, but I’m grateful that he taught me to take that leap in love. It seems like finding a healthy balance is key when it comes to putting yourself out there, and without someone urging me on, I’m not sure I ever would have found it.

So now, I’m finally ready to approach that cute guy at run club after work, or the young pastry chef at my favorite neighborhood bakery. After all, if I can book a flight to Michigan on a whim, I can certainly handle exchanging phone numbers with an attractive stranger and seeing where it takes us…


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