One Widow’s Adventure in the World of Dating


While definitely a time of hope and anticipation, the prospect of dating post-widowhood can also be a scary moment in time. However, by even so much as considering reentry into the “World of Dating,” you are actually taking a huge step forward on your healing journey; a step that is both “cause for applause” and congratulations.

My own “step forward” occurred roughly two years after my late husband’s death.  How did I know that the time was right to begin dating again?  Easy…I just knew.  I did not compare my timeline to the timelines of anyone else.  Instead, I tuned into and listened closely to my heart.  More importantly, I knew myself well enough to know that I needed to wait until I was confident that I was inviting other people into my dynamic for the right reasons; rather than to simply fill an impossibly large void.

Is the navigation of the World of Dating always easy or fun?  No.  Is it worth it?  Most definitely.  Travel back with me to a time when I almost gave up dating altogether; yet in perseverance, I also found my “happy” again.

The year:  2006…springtime

The time:  10:00 p.m.

Dress code:  Trendy-chic. High heels.  Smoky-eyed makeup.  You get the picture.

The setting:  Returning home from “first date” number 1,582,648.

Or so it felt.

It is at this hour that I disconsolately pulled into my driveway. I walked through the front door, kicked off the high heels and threw them across the room. They bounced off the sliding glass door and landed perilously close to an extremely startled cat, who looked at me as if to say, “What did I do?”

I’d come to the end of yet another first date / last date and what a catch this prize was. Need an example? When I arrived at the restaurant, he tried to greet me in a completely inappropriate manner… with an open mouth.

He wound up gulping air.

The evening progressed painfully slowly.  He sat way too close. He touched way too much. As this torturous evening drew to a merciful close, he had apparently saved the best for last … he’d lied about his age by almost twenty years (which I’d already figured out when I saw him).  He was baffled when I told him that we would not be going out again.

Once home and snuggled into my sweats with my usual post-lousy-date consolation snack of Coke and Doritos, I looked upward and started screaming at my late husband, as clearly, my having to date at all was his fault. The diatribe was something to the effect of, “You did this to me Fleet!  You said to go find love again. Find love?  Seriously?  I can’t even find decent conversation!”

After berating Mike in absentia, I decided that I was done with dating. I was finished wasting time, energy and makeup on idiots like the one with whom I’d just squandered three hours.  I decided that my life was fine as it was.

About that time, my teenage daughter came into the room. The thud of the airborne heels, the dazed cat and the not-so-subtle tantrum directed at her dad told her everything she needed to know about the evening.  I shared my decision to retire from the dating arena and just be on my own – since “alone” couldn’t possibly be any worse than the previous three hours had been.

After listening to me seethe, she quietly observed:

“It’s stupid to quit dating because of this guy.  Why should you have to spend the rest of your life alone because of a few losers?”

Since it’s hard to argue with logic, I reluctantly continued to date. I would love to tell you that nary a loser crossed my path ever again and the heavens opened and the angels sang.

But life doesn’t work quite that way.

If someone had told me that a year-and-a-half after this ill-fated evening would pass before I had the heavens-opening, angels-singing experience, I would have thrown in the proverbial dating towel (or taken that towel and strangled something with it).  It was indeed another year-and-a-half of dating what I have coined the “Loser Brigade”, before life hit me with one great big “I Told You So”.

The year:  2007…autumn.

The time:  Approximately 8:00 p.m.

Dress code:  Trendy-chic.  High heels.  Smoky-eyed makeup.  I don’t vary things much.

The reason:  Girls Night Out

I was in the bar of a fabulously-reviewed restaurant waiting for my fabulously-late girlfriend to arrive. Hungry, impatient and in need of a martini, I tried in vain to get a bartender’s attention. While edgily tapping my credit card on the bar, a handsome gentleman looked over and politely smiled.

His smile lit up the entire room and made my tummy flip.  I know – men aren’t supposed to light up rooms, but this one did.  As for experiencing tummy flips, I thought I’d left that behind about the same time I quit using Clearasil.

Then the Man-With-The-Room-Lighting Smile opened his mouth…and a British accent came out.  I don’t even remember what he initially said to me.  He might have said, “How are you tonight?”  He might have said, “Get out of the way warthog”.  With that accent, who cares?

As our small talk progressed, he told me that he was in town on business and that he lived in England.  Masking my disappointment, I continued our light conversation until my girlfriend arrived.  Prince Charming and I politely exchanged business cards and my girlfriend and I went in to dinner, where I spent the following two hours complaining that I would certainly never see this man again.

To my surprise, Prince Charming began emailing shortly after our first meeting.  He then began calling. Hours previously spent on stilted, job-interview-like dates were now spent blissfully engaged in fascinating telephone conversations. Yet, I was resolute not to fall for him.  Where could this possibly lead?  He’s in Jolly Old England; land of the Beatles, Burberry and bangers-and-mash. I am happily ensconced in Sunny Southern California; land of eternal sunshine, palm trees in parking lots and frozen yogurt.  Since I had dated men who complained about driving from one county to another, I figured that I was about as geographically undesirable as one could get.  I wasn’t about to fall for him.

Except…I did.

Two years after that chance meeting and a total of nine years after becoming widowed and convinced that I would never know light or love again…Prince Charming became my husband.

The lesson: Making a decision to return to the World of Dating is not easy.  Dating is not always easy.  It is not always fun and unfortunately, it is all but certain that you are going to run into at least one idiot.  However, if you decide that your life ended with the death of your beloved and / or if you decide that everyone in Dating World is carrying an idiot license because of the actions of a few – you are letting fear decide your destiny.  You are letting idiots decide your destiny. Neither death nor human being has that right and nothing should be granted that level of power.

Don’t give up on the prospect of companionship if you want it.  Don’t give up on loving again if you choose it. No one said it would be easy…but I would gladly go through all of the dating fiascos again for that one gentleman who still makes my tummy flip. Don’t give up, don’t give in…and here’s looking forward to the day that someone lights up a room for you too.

Carole Brody Fleet is an author and motivational speaker. Her books include ‘Happily Even After’, ‘Widows Wear Stilettos’ and ‘When Bad Things Happen To Good Women’.

For more information about Carole Brody Fleet, visit her website.

Inspiring Stories: Carole Brody Fleet

Inspiring Stories is a regular series featuring interviews and discussions with well known authors, motivational speakers and entrepreneurs from within the widows and widowers community. In today’s edition we chat to author, media contributor and public speaker Carole Brody Fleet.


Tell us a little about yourself and how you became bereaved?

By education and degree, I am a paralegal / settlement negotiator and after fifteen years in the legal profession, I left for an upper management position in the beauty industry.  My husband Michael was a 28-year veteran of his police department and in 1998, was looking forward to retirement and his next chapter. Our daughter Kendall, was nine years old at that time. In September of 1998, Mike was diagnosed with ALS (Lou Gehrig’s Disease) and battled the disease for just over two years before passing away.

Ten days prior to Mike’s death, our uncle very premeditatedly committed suicide. Three weeks after Mike’s death, I collapsed and subsequently underwent the tenth of what has since become thirteen major abdominal surgeries. Shortly after I recovered from surgery, my father was diagnosed with terminal liver cancer and died nine weeks later. All of these events transpired within a period of four months.

 You are a multi-award winning author with the books, ‘When Bad Things Happen to Good Women’, ‘Happily Even After’ and ‘Widows Wear Stilettos’. What motivated you to start writing?

Five years after Mike passed away, I was thinking about how little there was in the way of guidance and support for the widowed and began making notes on a legal pad.  When I’d finished, I had written what eventually became the Table of Contents for my first book, “Widows Wear Stilettos…”.  “Happily Even After…” followed and is a question-and-answer book for the widowed, while “When Bad Things Happen to Good Women…” addresses all manner of loss and challenge”.  In short, there has been a “work in progress” on my desk since 2005!

You are a motivational speaker to a diverse range of audiences, sharing your message of ‘What Now?’ and ‘What Next?’. Are you inspired by any particular group, more so than others? 

Each group is unique and I am always humbled by the reception and the response of the audiences. The one common denominator is a willingness to learn how to move forward from a place of pain and challenge to a place of peace and it is an incredible privilege to play a small role in that journey.

You have become a go-to expert on life adversity and grief recovery? What are the challenges involved in fulfilling this role?

Anyone who works in the self-help arena wants to help as many in need as possible. The challenge is realizing that no one person can appeal to absolutely everyone. I always encourage people to seek out that which best speaks to them and moves them in a positive healing direction, as healing must remain the most important focus.  However, the reality of not appealing to everyone in need does not remove the desire to help as many as possible.

Do you think widows and widowers are sometimes overlooked in terms of grief recovery and life changes?

Absolutely.  We are a loss-denying society and from how a widowed “looks” (i.e., “You don’t look like a widow/er”) to belief systems regarding dating / falling in love post-loss, moving homes, changing careers, etc., the stereotypes and stigmas surrounding widowhood unfortunately remain constant. It is easier for the world at large to try and sweep the widowed aside as if widowhood is a contagious disease; rather than treat it as a life-altering event that deserves acknowledgement and compassionate support for those affected.

You have spoken a lot about the importance of gratitude. How have you made this a part of your life? 

Every night, I stop and review my day to find the blessing in it. I’ll be honest; there are days where I have to look really hard for the blessing – but the blessing is always there; even on challenging days.  My attitude is always one of gratitude, because I have lived and continue to live a very blessed life.

Can you share with us five things which have helped you through your bereavement?


– What one book?

 It’s a tie between “Living Judaism” by Rabbi Wayne Dosick and “Seven Prayers That Can Change Your Life” by Dr. Leonard Felder.  Both books were instrumental in helping me let go of the anger that I experienced going back to when Mike was initially diagnosed.

– What one activity?

My “quiet time” each evening, designed to help me cope with the grief that we all “set to one side” during the day in the interest of work, children’s activities, etc. Whatever “front” that I had to present during the day came off at my designated Quiet Time. Possibly the healthiest thing that did for myself during grief recovery. It is a tactic that I recently and tragically had to re-employ…and it still works.

– What one quote?

“While loss or challenge will shape you, it does not have to define you”.

  It is my own quote and one that I both teach and live by every single day.

– What one piece of advice?

I had been widowed for a year when my mother gave me very wise advice. She told me to stop and look back at how far I had progressed since Mike’s death. When I actually examined how far I’d progressed to that point, I began truly appreciating the healing that I had accomplished. To this day, I still pause and look back at how far I have traveled since that horrible season in time when I thought that I would never see light or know love again.

– What one song/piece of music?

A beautiful South African lullaby called, “Thula, Thula”  (“Hush, Hush”) that I grew up listening to  (we were a musically eclectic household).  After Mike died, Kendall and I would often cuddle and I would sing the song to her. We still turn to that song for solace and for peace.

More Info:

Carole Brody Fleet is an author and motivational speaker. Her books include ‘Happily Even After’, ‘Widows Wear Stilettos’ and ‘When Bad Things Happen To Good Women’.

For more information about Carole Brody Fleet, visit her website.

This article is part of the ‘Inspiring Stories’ series.