Dating Again, After a Long Marriage: Awkward. Thrilling?

When my husband of 20 years asked for a separation, I had the sensation that my world was crumbling. I left the couples counseling session, numb—shocked that my car was right where I’d left it, with a ticket on it, confirming that good things, weird things, horrible things still happened, and time ticked on, regardless.  Our relationship had been deteriorating for a while, but I was like the violinist on the Titanic, playing my heart out ’til the very end, choosing to ignore the water gushing in all around me.

The months that followed were a blur.  It was an era of Netflix, drinks with friends (anyone left who would still listen), Rodney Strong cabernet and Trader Joe’s sea salt and turbinado-dusted dark chocolate almonds.  I did the things you are supposed to do to cheer yourself up: bubble baths, Deepak and Oprah meditations, retail therapy and Stuart Smalley-like, “You got this, girl!” daily affirmations.

Dating was a foreign concept.  I remember being out with my friend David, a survivor of divorce, during a particularly brutal chapter of dealing with my ex and learning the details of his affair that preceded our split.  David assured me I would feel better some day, date, and have sex again.  This sounded crazy to me­­.  He may as well have said I was going to get my aviator’s license and become a fighter pilot. 

My bedmate was a scrappy 22-pound mutt whose breath smelled like a canning factory.   I told myself he was all I needed.  I could not imagine wanting to date.

But then, walking the dog one night, I spotted a handsome man exiting the liquor store on Ocean Park Boulevard. He strolled past me with a bouquet of flowers in one hand, and a bottle of wine in the other.  I winced so sharply it was almost audible.  It was a “click moment” for me, one of those instances that click everything into focus.  I wanted that man with the flowers and wine.  Well, not him, per se, but a man.  I wanted a man who would think of me, buy me flowers, pick up wine to bring home to me.  I was lonely.  I wanted, and it was sort of nice to want.

The questions that followed were these: Who did I want? What did I want? What is dating like today?

As I navigated the post-marital dating waters, I learned first-hand that dating has changed drastically since the ’90’s.  For one thing, it’s electronic, mediated by technology.

I remember toward the end of my marriage, a commercial for eHarmony came on the television.  The man said there was a questionnaire assessing 29 levels of compatibility.  Looking over at my husband, passed out in front of Sports Center, I felt a moment of panic.  We both loved our two children and hated Jethro Tull, but did we have 27 other levels of compatibility? Probably not.  

Have the signs of exclusive commitment also changed in today’s dating world, I wondered?  In the past, they were physical.  Cameron Crowe put it so perfectly in the movie Singles.  In grunge-rock-era Seattle, giving your significant other your garage door opener meant you were taking the next step, you are in a serious, committed relationship.  What’s the garage door clicker equivalent today?

 I always said I would never go online and make myself vulnerable to strangers on the Internet, but on the night of wanting the man with the flowers and wine, I spent two hours researching how to create the perfect OK Cupid profile, complete with clever handle.  I created a profile, with a clever handle.  I was terrified.

I started dating, playing in traffic.  I had my first few Tinder and OK Cupid dates.  I had a short-lived fling with a man-child in Venice beach—an old friend whom I had known for many years.  I  reconnected with an old crush from my hometown on Facebook.  Then we met in person when I visited my family back in New York.  We ended up having a short, amazing fling.  It was exhilarating, unencumbered and hot.  My therapist practically jumped up and down when I told her about my romp in the East Village.  “You had baggage-free sex!  Isn’t that great?!”

It was great, actually. 

As I took stock of my new life, I realized that not only has dating changed, but I’ve changed, too.  What I want is different.  

The last time I dated, I was in my late twenties.  My clock was ticking.  I was looking for The One.  He had to be my Everything.  And, as if that weren’t enough, he also had to have kickass genes to carry on my family line.

Now, I’m approaching fifty.  I am the mother of two incredible boys.  I’m not looking for someone to father my children and meet all my emotional needs.  I just want to feel alive.  I want to have fun.  I want to date someone who is not in a godforsaken “open relationship” (truly a phenomenon on OK Cupid).  I want someone who will respect my space, my family time and not look to me to be his Everything either.


And then, along came Michael.  He wasn’t chiseled with perfect genes.  He gesticulated like Woody Allen.  He was a professor at the local community college, crazy, sweet and with a very interesting mind.  On our first date, when most guys are busy trying to impress you, Michael told me a long, shaggy-dog story about Facebook, the older girl-next-door he knew when he was nine (she was 10) and how, many moons later they had a two-year relationship.  It had just ended, he said.  We agreed that we were both post-traumatic train wrecks.  I said yes to a second date.

On our second date, after drinks on Main Street for St. Patty’s Day, we took a romantic walk on the beach that quickly turned very slutty, and kind of awesome.  The next day, as I smiled remembering it all, I thought: Since I’m not looking for The One to marry and father my children, maybe I’m more on a more day-to-day plan? 

Maybe I want the “one for right now,” with a little “o”? The one I want to hang out with at the airport flea market, run away with for a weekend, order takeout Cha-Cha-Chicken with, and rent movies? 

We kept dating, and after a few months, I found myself wondering how I would know when (and if) we’d entered a committed relationship.  Then Michael told me about a teachable moment with his students at the college where he works.  He was talking about symbolism, and he equated the garage door clicker scene in Singles to the traditional giving of the engagement ring.  I couldn’t believe  it!  He referenced my favorite scene in a movie by one of my favorite directors?!  Was this one of the 27 levels of compatibility on EHarmony?  We both got tested for STD’s and I quit off OK Cupid.  Was this the next “wearing his ring on your chain” level in a relationship?

This month, the kids and I moved out of our family home and into an apartment.  It was a very difficult and challenging move for them, but ultimately, liberating one for me.  I hadn’t realized how much I needed to take the next step in my divorce, to have a home of my own, one that is not part of my marital past.  When the landlord handed me the garage door clicker to my own place, I felt a surge of love—for my newfound freedom.  It was a “clicker moment.”  I don’t know if I’m ready to give Michael my garage door clicker just yet, but I do know that I am in love with having one all to myself.  


Rebecca Cullen is a television writer and mother of two in Los Angeles who recently separated from her husband, after 20 years of marriage. She's now writing about her new single life.