Two Roads Diverged in a Wood…and I Took the Dating Road Less Traveled By

In high school, I remember reading Robert Frost’s infamous poem, “The Road Not Taken.”  Little did I know then, how that poem would become a reality for me as a dating adult.

Let me refresh your memory with its famous three lines of prose:

“Two roads diverged in a wood, and I—

I took the one less traveled by,

And that has made all the difference.”

In those pubescent, poodle perm days, my immature brain couldn’t relate to Frost’s vision of taking the road less traveled.  Heck, the only road I envisioned consisted of the driver’s ed course which ultimately led to my four-wheelin’ freedom.

But over the years, through my personal ups and down, I have found myself standing at a multitude of crossroads…recollecting on Frost’s sentiment that trekking the unfamiliar path – ultimately leads to a big positive difference.

Don’t worry…I’m not going to bore you with a bunch of stories centered around drama-filled life decisions like career moves, marriage, divorce, and which lipstick I buy at Sephora….blah blah blah.

Let’s simplify it or as I call it …“juice-ify” it.

In dating…we “chicks” often stumble upon “Two Roads Diverged in Wood.”  Women in their 30s find themselves staring down two different paths – when it comes to ONE guy.    Let me paint the picture.  When you meet a potential person of interest out on the town (a.k.a. some dude you think is somewhat hot who actually has a decent job)…you IMMEDIATELY make a choice.  A.  You put him in the friend zone….or B….You chase after the romantic relationship with the BIG chance of losing the friendship all together.  (NOTE:  B is most always the road less traveled.)

As a woman in this age bracket, this dilemma has smacked me in the face numerous times.  After sleeping on it (and drinking heavily while discussing this topic with gfs) I think I have an answer about why we struggle about which path to choose.  Mostly, it’s about the RISK. Do we go after something which ultimately MAY turn out wonderful, yet end quickly?  Or do we save face, take the safe route, and put the guy in the “you’ll never hurt me” zone.  After all, he’ll be around forever then.  Ugh.

The problem is…women in their 30s have built a wall around themselves that’s impermeable.  We’ve becomes “aces” at protecting ourselves.  Just like we’re pros at balancing our own checkbooks, buying our own houses, and organizing our own vacations.  Why open up a potential can of worms filled with tears and rejection when you can avoid all that crap all together?  Hmmmm….  In the long run, it’s simply the no-brainer to play it safe.

To those of you married, this conundrum may sound odd.  You probably think it’s easy when meeting a guy to immediately know “what to do”…what decision to make…and if the guy gets a “thumbs up or down.”   Welllllll………..its not.  It’s a vat of confusion mixed with self pride and peppered with teenage anxiety.

Recently…two roads DID divulge in my personal dating world.  It all started when I met a cute guy randomly at a wine tasting. He’s an optomestrist…so for the blog’s sake, I’ll call him “Eye Guy.”  Like me, Eye Guy is a “Denver transplant.”  I couldn’t quite determine whether he was interested in ME – or just interested in just networking with my friends – expanding his social circle.  But I decided to hang in the weeds, rather than choosing my path, biding myself some time.

A few weeks in…after many shared conversations with Eye Guy…I found myself at that fork in the road…

So…after following my gut…

I threw on my hiking boots and took the path less traveled by…

So far….it IS making ALL the difference…not just in my life…but I hope his.

To the rest of you…I say go for it.  You need the change of scenery.