Lifestyle & Culture

Late Dates #1: In the Beginning


A gray DWF of a certain age, who’s a former nurse anesthetist, financially secure, securely attached, an intuitive empath and recovering perfectionist, desires LTR with a mature, emotionally stable, open-minded man. Grace Cooper (a nom de plume) shares her advice on how to navigate the 21st-century’s The Dating Game.

By Grace Cooper

ENTERING the dating rodeo at this stage of life is inadvertently inane, frequently insane, but always an opportunity for transformative self-inquiry, fresh perspectives on life…and a few belly laughs, too!

Thirty-eight years ago, I married a man with whom I had nothing in common. Initially, I admired his intellect and ambition. He, on the other hand, never admitted to liking much about me, was cold, remote and critical. He reminded me of my self-absorbed and competitive mother. Predictably, she adored him and advised me to make the match official. So, I obliged by marrying a male version of my mother.

Despite raising two great kids and forging successful careers in medicine, we were unhappily mismatched from the very start in every way imaginable. Eventually, I begged him to attend marriage counseling with me. After six months he dropped out. The therapist advised me to divorce him ASAP.

“In all my 30 years, I’ve never seen a more dysfunctional marriage, “ she confided in me.

“He gives you absolutely no credit for what you bring to this relationship” she continued. “You need to build a life of your own…discover your own interests…make your own friends.”

And with that, she handed me a copy of Codependent No More by Melody Beatty.

She was right, but still, it was seven more years before I could bring myself to put asunder the promise I’d made decades before, and another few years before I considered the role codependency played in my life.

My not-yet-ex met his third wife a week after he moved out. I embarked on a different quest—to discover who I was then, am now and may still become.

Initially giddy to have the freedom to reinvent my life, I soon found myself increasingly disoriented and depressed. After all, I’d been attached to one man or another since my teens, as were most women I knew. Yet after I divorced my husband, one by one, most of my married friends stopped calling. The new friends I was making now were mostly divorced or widowed women, many of whom were bitter man-haters or undeniably depressed. Ugh! I was 57 years old and felt as if I’d taken a swan dive off a cliff without considering how much the landing would hurt.

I joined Meetup groups. I adopted a dog and walked him around my neighborhood, smiling at every interesting man who wasn’t sporting a wedding band. I went to concerts, restaurants and adventure traveled with female companions. I volunteered widely. Yet, always in the back of my mind was the most elusive of reinvention goals— I wanted to be part of a happy couple—for once!

Finally, at the insistence of my sympathetic millennial daughter, with great trepidation, I launched my first foray into the world of internet dating. My daughter insisted it was a safe and common way for her generation to meet men. However, I didn’t know anyone my age who would even admit to engaging in the internet version of The Dating Game–modern meat market—accessible to millions via the Web. Facebook aside, I could not imagine feeling so publicly exposed, but what alternatives were there? I rationalized that online shopping was an efficient way to survey a wide variety of wares in the least amount of time. Would shopping for a new potential partner be equally efficient? The longer I thought about it, my chances of meeting a future mate reaching for the same cantaloupe at Whole Foods seemed more romantic, yet highly unlikely.

Ultimately, I held my nose and signed up for a three-month trial period on The site makes it easy to upload a recent photo or two and a self-descriptive essay, including activities you like to do. There are screening parameters you set as to geographic distance you’d travel to meet, as well as religious and racial preferences, and even body type. So far, so good.

Any worries that no one would want to date me were quickly erased, when, as a new member of the community, I found myself overwhelmed with prospective suitors. However, rather than the romantic and witty introductions I anticipated from mature men, many of them came on to me as sharks might circle fresh blood in the water.

Some demanded I post a photo that revealed my full torso, complaining that most women post photos from 20 years and 30 pounds ago.

“Yeah, right, nothing like walking into a blind date only to see disappointment register on a man’s face,” I joked—but they weren’t joking at all.

Online dating starts out with the shallowest of attractions. Physical attributes are the “bait,” but if that’s not sufficient, many list photos of fancy cars, boats, foreign destinations, skiing shots, piloting a boat, all to suggest wealth, health or success. Others posted smiling photos of themselves walking daughters down the aisle, cuddling puppies and adorable grandchildren, presumably their own. Many other men—for reasons I cannot fathom—are pictured straddling huge Harley motorcycles or a freshly slaughtered deer. More commonly, it’s a fish—a big freshly caught fish. I can’t even . . .

But then there were the emails from those men who started out appropriately friendly but quickly devolved into their sad tales of how long they’d looked for the women of their dreams, how many women ignored their inquiries and how nice I seemed that I replied to them at all.

Quickly, I learned that men of a certain age are, for the most part, no longer feeling like captains of industry or king of the tennis court.

Health issues, waning careers and financial assets halved—even hair loss. These guys were often humbled, if not brought to their knees by various iterations of an existential crisis.

I was now sufficiently intrigued to learn more about men my age. So, when the first interesting man suggested we meet for a real date, I pulled on a pair of Spanx, stuffed my feet into uncomfortable shoes, applied some makeup and even combed the back of my hair. Little did I know this was to be the first of my 150-plus first-and-last-dates.

Next up: Repetition compulsion or why we do the insane things we do—like date the wrong type of man over and over again.


—Grace Cooper (a nom de plume) left her long marriage a decade ago, and with it went all sense of her identity—but not for long. Now 67, she has begun chronicling her tales of looking for love in all the wrong places, and unexpectedly finding herself.

10 thoughts on “Late Dates #1: In the Beginning

  1. Ernie says:

    Yes, more please!

    1. Janet Kelly says:

      Next week!

  2. Nancy G says:

    You are going to continue this as a series, right?

    1. Janet Kelly says:


  3. Marion Lewis says:

    Great article! Authentic and funny. I can’t wait to hear more!

  4. Alex says:

    This is one of the best Little Bird columns I’ve read in a long time. What happens next? Please post a follow-up.

  5. Jean Anne Hattler says:

    Wow! What a beautiful, touching and authentic piece you have written. You show great strength and vulnerability. I look forward to your next post. Brava!

  6. CB says:

    Fantastic article spot on and very well written!!

  7. janet kelly says:

    I got divorced when I was 30. I knew I had made a mistake in marrying this guy when I heard him on the phone yelling at his ex-girlfriend.

  8. Maureen Young says:

    Loved this column! I had similar marriage experience but wasnt brave enough to go online. More please!!! Can’t wait to read another chapter!!!

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