Online Dating in Act Three

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online dating, the three tomatoesI have been inordinately fortunate on, with 800+ people “viewing me” and about 200 of them actually emailing me.  Most who write are completely inappropriate—too young, too far away, too needy, too crazy.   But there are gems to be found.   I know I will find mine.  But oh what a journey!

I thought I had won the prize right out of the box six months ago.  After only two weeks on,  I met a gorgeous man, tall handsome, but unfortunately, retired. I didn’t think this would be a problem, because I was naïve.   In our four and a half months together I was soundly wooed, wined and dined, taken to St. Lucia and to Fort Lauderdale, where we stayed at an oceanfront high rise, fished off his son’s yacht and just had an incredible time.  Returning to New York he dumped me on Valentine’s Day.  The reason:  he wanted to move to Florida posthaste, full time, no being snowbirds as he had originally described what our future life together could be.  My unwillingness to chuck my  business and my fantastic Manhattan life, sell everything, roll up the carpets and move to Florida to live on a golf course in an adult community stymied him and killed the dream.

It hurt for a few days, but as for the scenario he had in mind, just shoot me dead.

So….after that I changed my MO.  I would only date two types of men:  One, youthful, fully engaged (i.e. not retired) men in my appropriate age category, around  60 to 75;  or Two, very, very old men of around 85 to 95 who were near death but fascinating to spend time with.  I now have dates with two of the latter lined up, one age 88, a Harvard doctor, great raconteur and very funny too, and a 90 year old a friend wanted to fix me up with, also highly accomplished and eager to meet dynamic, attractive women.  Here’s my only question:  is  it possible for a man to die from an overdose of Viagra ?  And if so,  would the authorities blame the partner who encouraged it?

This weekend, besides my 88 year old on Friday night, who said he wants to take me to an amazing French bistro for dinner, I have a fourth date with a lovely man, age 74, who is an entrepreneur and world traveler.  The challenges there: he has a house in a lovely, leafy community on Long Island that he says he will never leave to live in the city, so living together is impossible, and I do want that, eventually.  Plus he has a cat who would not get along with my two little dogs.   Additionally, and here’s the biggie:  he needs knee surgery and so right now can’t walk more than one block, which, he explained, is just temporary.   He is willing to drive me anywhere but we wind up staying in.  I like him a lot but I think I will put our relationship on hold till he has his knee surgery  next month and recovers.  Which may end it, but I am not sure I want to keep staying in on Saturday night, even though he has us order in.  I do at least like to go to a movie, don’t you?  However, he too is a great talker and a funny guy.  Undecided,  We’ll see how Saturday goes.

Here’s my observation, based on about six months or so experience:  I believe there is no shortage of great men in our age group, ladies….actually no shortage of men in any age group.  When you filter out the idiots…like the 75 year old who said he wants women 30 to 47….how’s that working for you, Grandpa?….there are still a treasure trove of warm, attractive, loving men.  All you need is one, but of course you have to shop a lot to find the perfect “buy.”  I am in the shopping stage now, learning a lot, so that when I email the ones who interest me, a get increasingly clear and decisive and what I actually want and need, not just trying to be what they want and need.

If anyone cares, I will keep writing about my experiences in this brave new world of online dating, boomer style.

Love to hear from you about YOUR online dating experiences.  And if you want some tips on what kind of bait to put on the hook to catch the right fish, well, I am pretty good at it, so just ask.


  • Judy Katz

    Judy Katz is a book collaborator, ghostwriter, publisher, and marketer. Along with obtaining literary agents and publishers for her authors, she helps promote their books to serve them as the ultimate reputation-building tool. Her most recent project, published in late November 2022, A Question of Respect: Bringing Us Together in a Deeply Divided Nation, has garnered significant media attention and is a WSJ Bestseller! A Holocaust memoir, Angel of the Ghetto, was award-winning and inspired a documentary. To date, she has completed 50 books. Judy also writes a regular CelebrEighty column. These popular essays on changing the conversation about aging appear on SilverDisobedience.Rocks and the @SilverDisobedience Facebook pages. A graduate of UC Berkeley, Judy wrote a weekly column, "Meaning's Edge," in the Daily Californian for all four years. She later wrote for a medical ad agency and two McGraw-Hill Magazines before becoming PR Director for Madison Square Garden, the New York March of Dimes, and Director of Special Projects for the National MS Society. At age 65, Judy found her true calling when she began helping people become successful authors. A proud member of the Author's Guild, PEN America, and other professional and networking organizations, Judy is on LinkedIn and Facebook. You can contact her at 212-580-8833,, or

2 Responses

  1. Mary Beth Nadler says:

    How true, how true!! I get so discouraged that I have to laugh. I usually sign MB instead of my name as most men can’t comprehend an Irish Jewish lady, they either want to return me to the faith or run. Meeting someone for the first time is tricky. Their photos must be of their son. I have walked right pass quite a few and unfortunately didn’t keep walking. My photos are current and I got caught. I think my next post will be “looking for a rich handyman who loves to travel”. Good luck on your journey, love to hear from you. MB!!

  2. Susan E McKnight says:

    You are very lucky. In Buffalo there just isn’t many ‘eligible’ men as you describe, or at least they do not answer my posts. It seems men around here want 15-20 years younger, or Barbie aged dolls but not many of them! I am 68/everyone says I look fabulous and not my age, I take care of myself But I have not met a good man who matches me………with my energy, happiness, adventure, etc. So now I am worried its Buffalo.

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