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  • Writer's pictureKim Carillo

Sixty And The City

New Yorker, Ellen,  shares her hilarious dating stories in her fabulous blog “Sixty And The City.” I am so excited to welcome her here.  Ladies…as Bette Davis once said: “Fasten your seatbelts, it’s going to be a bumpy night!”

Still dating at 60? How can that possibly be? 

When was the last time you read anything about women dating over 60? How about NEVER?

I’m here to open up that conversation as we’re here and we need a voice. 

BTW, when I say over 60, I’m talking of women who are still vital, successful, fabulous. 

We take care of ourselves, dress well… age appropriate but never matronly. We are active, informed, educated etc. 

Some of us may get a little injection here or there but fundamentally, on some level 60 is the new 40. Now, if only someone would tell that to my knees! 

The truth is that this Ellen is much more fabulous in every way than my younger self.  I’m more self-assured, I know what I want and I’m not afraid to ask. I’m also comfortable in my body which was something I never was as a young woman. I’ve been single for fifteen years and have two amazing grown up daughters.  They were the ones who encouraged me to write about my dating experiences!

So what does a woman over 60 want? We want a nice guy who is fun and youthful and wants to be loved by a great woman. 

Key ingredients are common interests, sense of humour and the desire to have the connection. Great or warm and loving sex wouldn’t be bad either. Yes, we still like to do that! 

At this point, we all have baggage but as long as it’s not all consuming, it is what it is. 

Why is it so hard to find? 

Dating at any age is never the easiest. I remember suffering through many hideously boring dates when I was a much younger woman too. 

At this age, it’s like nothing one could possibly imagine. When I tell my “adventures” to my friends who haven’t had a date since Reagan was president, they stare at me in disbelief and then break out in paroxysms of laughter. Trust me, these stories are not tales that one could possibly make up! 

These days, in order to meet that special someone, one has to go online. Holy hell, who invented these sites? Someone very smart and also a bit sadistic, that’s who. 

Match, OkCupid, Jdate, and my favourite, not really, It’s Our Time which should be known as It’s Our Time For Married Men and Scammers! 

In addition to the sites, there are the apps: Tinder, Bumble, Jswipe, Coffee Meets Bagel.  

My first date, post divorce, came a year after my marriage breakup and had nothing to do with an online site. It nearly wrecked me but I am so glad I did it.

It was with my boyfriend from senior year in college. Over the years, we had kept in touch intermittently.  Turns out he too was separated although he hadn’t gone through the whole process yet.  Now, hold that thought, I will get to it.

We arranged to meet for dinner.  But what the hell was I going to wear?  After discarding nearly every article of clothing I owned, I finally settled on understated and FABULOUS for the big reunion.  Now all I needed to do was figure out how to iron my face before I got to the restaurant! I prayed for ambient lighting. 

Luckily, he didn't see the current me but rather the young girl whom he had fallen in love with in college. Ditto for me. He was crazy about me a gazillion years ago and apparently, it hadn't worn off. Could I pass out now just writing this? 

Sitting over dinner, we chatted about the usual things: kids, life, work. No discussion of my ex and his "almost" ex. 

We sat and talked for hours and when he kissed me goodbye, I almost collapsed. He was a world class, awesome kisser plus I hadn’t been kissed in years and certainly not like this. 

Right now, I cannot remember where we went for the second date other than it was a very romantic place in SoHo. Quite frankly, it could have been McDonald’s with great wine and soft lighting. Who cared about food? 

That part of the evening went by in a blur. Yes, I was acting like a besotted 20 year old and damn, did it feel great! 

Next thing we are at the Gansevoort Hotel which, BTW, is blissfully dark. OK, so we brought up the median age by at least 20 years but who cared? 

As we got into the elevator I started to feel like I was going to pass out. Was I really going to get undressed in front of someone who knew me when I was 22? 

While I was hyperventilating and sorting through “outfit” choices in the bathroom (shower curtain, towels, robe) he ordered up a bottle of excellent champagne. After my initial hysteria and two glasses of Dom, I got over myself. 

Kids, it was like time had stood still. Always fabulous, he had gotten better with age. Is that even possible? I NEVER wanted to go home but kids, job etc. beckoned me. 

What followed can only be described as a true love affair.  We were crazy about each other all over again except this time, it was even better. We acted like kids and it was pure unadulterated bliss. 

This man wrote me love letters or should I say love emails? OMG, just thinking about them now, I get weak at the knees. It’s hard for many men to just say those three little words; “I love you”. Well, blissfully, not this guy. 

For over a year, we both walked around with a perpetual smile on our faces. With his kids and my kids and jobs, we didn’t get to see each other as often as we would have liked but that made our time together even more precious. 

Well, my friends, be still my heart, around the bend was a big fat problem of which I was totally unaware. In retrospect, there were some hints but I chose to ignore them. Of course, I did. Reality was not going to spoil my buzz. 

By this time, of course, we knew all about each other’s kids and much of the details about our unsatisfactory marriages and my nightmare of a divorce. He never mentioned any details about his separation, which I should have taken as a warning sign but no, as above, reality is highly overrated. 

One of the things that I most adored about him was his unabashed love for his daughters. His apartment was a few blocks away from his girls and he saw them several times a week. A man who is devoted to his kids is a man we all want to love. 

We were sitting at lunch one day and next thing I know, he was crying saying how much he missed being a part of his kids’ everyday lives and was moving back home to be with them. 

Did he love me as I loved him? Without question but he needed to be with his girls. I tried to talk to him about it but clearly, this was not a decision that could be changed. 

We hurriedly settled the cheque and came out into the blaring sunlight of Broadway/38th Street. For once, I wasn't obsessed with lighting. 

I couldn’t allow myself to freak out because in those days, I was bound to run into several people I knew from my industry on the street.  Sobbing hysterically and holding onto his leg (figuratively) while trying not to throw up was not an acceptable plan! 

He hugged and kissed me goodbye and literally I felt like I was going to drop dead on the spot. 

We did see one another a few times after this as neither of us could let go. The last time this man kissed me goodbye is a moment I will never forget. 

Clearly, I was devastated. Fortunately, I had two kids for whom I was totally responsible so going to pieces was not an option.

Thankfully, I am resilient so I pushed myself through the heartbreak and spent a lot of time in the bathroom with the shower on sobbing into a towel.  But, I got through it. 

Was I happy that I had taken the leap with this man as my first foray into the world of being a middle-aged single woman? NOT EVEN A QUESTION. As a matter of fact, I would do it again, even knowing the outcome. I was lucky to have found him when I did.

Also, it reminded me that not only could I love someone but could be loved back. 

Next stop after this was online dating. Of course, it took me over a year to jump in. Talking about reality testing. Ugh!

One of my first dates from the sites sounded fabulous “on paper”. Now, I will admit to significant naivete as I had no clue that so much that is written on these sites is about as real as unicorns. I was trying to tamp down my inner cynic and just go with the flow. 

He was attractive, tall, had tons of similar interests, a devoted dad or so he said, was financially secure and lived in the city.

Dick and I made a date to meet at his beach house in Westhampton the following Saturday and  go to dinner from there.

It was one of those beachy upside down houses with all the living quarters on the first floor and the bedrooms downstairs. Wrap around decks and a gorgeous sunset. I was psyched to meet him and to sit drinking a glass of wine while enjoying the view. And conversation, wonderful conversation as this guy, “on paper”, was very smart and well read. 

He was waiting for me at the door and yes, he looked like his profile and he really was tall. Again, not being internet dating savvy, I could have been greeted by an 80 year old. But he was not yet 50, a few years south of my real age. 

His greeting to me was "cute, very cute". We went out on one of the many decks and had a glass of wine. After a second glass I suggested that we should leave for dinner as I needed food. 

He excused himself and dumb me, thought he was confirming a reservation but out he comes with some desiccated chicken cutlets wrapped in crinkled up aluminium foil and asked if I would like one. I wasn't expecting a 4 star restaurant but leftovers on a first date?

Very diplomatically and oh so sweetly, I said that I would much prefer to go out for a casual dinner. Cue to him: casual connotes beachy, not crazy expensive. 

After a quick trip to the powder room, I sashayed into the kitchen to find Dick doing the full monty. YUP, NAKED!! Apparently, the menu consisted of gross chicken cutlets and him with a side order of me. No, my friends, I did not run out the door. I actually started laughing. 

My laughter had nothing to do with how he looked as he actually looked damn good but who cared? My laughter was at the ridiculousness of the situation!

I told him, sorry he had the wrong girl and walked out. He followed me out the door still naked arguing with me about what a good time we were going to have. Was he kidding?  No!!  Apparently, he also didn’t seem to care that he was giving his neighbours quite the view. 

One cannot make this stuff up. Moral of the story: beware of what appears to be "good on paper". Also, some people are very aptly named. His name was Dick and he proved to be just that: "A DICK"! 

But, as crazy as this sounds…there was worse to come with my next foray into the online dating game!  

Check in next Friday to hear the whole horrifying story and get Ellen’s five top tips for dating in your fifties and sixties.

To follow Ellen on instagram: @sixtyandthecity

To read her Blog go to:

Do you have a story to share?  If so, fill in the form on the 'It's All About You' page or email me on:


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