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Dating In Your 50s- Open Marriages, Man-children and Men with Big Fish

Dating In Your 50s- Open Marriages, Man-children and Men with Big Fish

If you’ve been out there on the dating scene for many years, you’ve had a chance to navigate the fraught waters of online dating. But if you’re 50 and you find yourself suddenly “out there,” single after a long-ass relationship, online dating may feel more like playing in traffic than having fun. You’ve changed over the years and dating–well dating has really changed. 

On the upside, many people find their true soulmates who are also newly single online. The internet can be a great connector for anyone who doesn’t have the time or patience to wait for Mr. Right to appear in front of them at the prescription line at Walgreens or a “meet cute” in the Trader Joe’s parking lot where you exchange numbers after a minor fender-bender. 

And technology is not the only disruptor at this point. Dating at this age is completely unlike dating in your 20’s because your biological clock has officially stopped ticking. Chances are, if you have just gotten out of a long marriage, you may not necessarily even know what you’re looking for. Your heart may be temporarily closed for repairs. 

For me, I had been there and done that when it came to finding The One who would be my best friend/turn me on/be a great husband and father some genetically-stacked children. 

As I navigated mediations, and later, court appearances, staggering lawyer’s bills, selling my home, and downsizing, I was looking for none of those things. I was living in the moment. I desperately wanted to have some fun. I wanted to wear sexy shoes and leave the house. I wanted to have a reason to get waxed within an inch of my life. I simply wanted to find someone I enjoyed who enjoyed me. 

I approached the whole idea of putting myself out there in traffic as a project–a nerve-wracking next step in my singles’ journey. 

A thorough research nerd, I figured that before creating an OK Cupid profile, I would learn what worked, and I researched how people chose a handle. I picked an awesome name and decided to have fun with my profile. Then I dove in, head first. 

And there they were, a parade of single men, also “out there,” like me. I pored over their profiles as part of my research. Judging someone’s character simply by a few poorly-lit bathroom pics and car selfies (let’s hope that they are stopped at a red light when they pose for these) can be challenging. 

And then there were the fish. No matter which dating app I checked out, there they were, a sea of rugged men outdoors, either holding fish, fishing rods, or proudly displaying a fish on the boat that they had lured/dangled/caught/clubbed. 

Was this supposed to turn me on? I was having flashbacks to our cat Pearldrops in Brooklyn, proudly dropping a dead mouse in our kitchen. She was so confident that we would be as excited as she was to see his lifeless body and skillfully broken neck. I’m sure our horrified reaction was not the reception she was hoping for.

Attraction is a highly subjective thing. There are sociologists who have studied what people find attractive in a potential mate, and it’s interesting how norms and culture have affected what people consider desirable in a potential significant other. I read some articles as part of my research. 

Reading this stuff gave me some perspective. Were these big fish guys displaying some Neanderthal hunting/gathering prowess? Did they simply not get the memo that this is no longer a thing with us modern gals? I felt like writing to a few of them and suggesting, hey, could you pose reading a New Yorker leaning on a Prius, or enjoying a lobster roll at a food truck–something, anything that did not involve dead fish?

The good news is that if there is a segment of ladies out there who absolutely love fly fishing and get lured by a flashy lure and some chaps/gators, worms, and flannel, there are thousands of men out there just dying to meet you!

My first OK Cupid date was with a sweet, attractive guy, probably a few years younger than I am who lived in the suburbs with his wife and kids. Since I had read his profile, gotten a glimpse of his photo and had a nice exchange with him, my curiosity was peaked. 

We met up at Ceviche in Venice for margaritas (and ceviche) and he explained how his wife had surprised him out of nowhere with this idea of opening up their marriage. I listened politely and wondered if this was a new model of marriage that really worked, or was she simply not into him any-more but she really liked the house and the co-parenting help? 

We had a perfectly nice dinner and a lovely stroll down to the beach. I suppose if I had any chemistry with Married Guy from the Suburbs this situation could have some potential for a no-strings-attached companionship/sex thing for me, but when we kissed on the beach I felt nothing. He was adorable, but I really just wanted to go home and binge on a few episodes of House Hunters International, have some sorbet and go to sleep. 

Apart from the married guys, I discovered another subset, which worked for me for a while: the man-child. He never got married, settled down, had kids, or any real responsibility. He looks great, (no dad bod there), works out obsessively, dresses stylishly and is always up for anything–beach day, road-trip, lost weekend in bed. 

On the downside, if you start to develop feelings for a man-child, you come to realize that his track record of not lasting in relationships is due to being a self-involved Peter Pan who either cannot recognize the needs of others, or simply isn’t too interested in them. If you can fit into his schedule and his lifestyle, you’re awesome, and if you’re not into exclusivity, this could totally work. But if you’re a grown up looking for a deep soul connection, you should be aware that you may have a shot at being fourth or fifth on his list of priorities, but you will never be bumped up to number one or number two. 

John Hamm so perfectly embodied the man-child in Bridesmaids. I love when Kristen Wiig finally wises up and dumps him and he screeches off in his Porche, yelling out, “You used me! No big deal. You are no longer my number three!

Five years later, I can safely say that I got over those initial fears. I dove in not knowing what to expect and I ultimately ended up meeting two amazing men who I did not toss back in–one who would become an awesome friend and one who turned out to be the rarest of fish–a soulmate. 

From my time in the trenches, these are 6 crucial tips to master online dating at 50.

Stating your age

If you fudge your age, that’s OK because guess what, so do they! My advice–shaving off a few years so you fit into some algorithm is fine. Shaving off a decade-no. Posting old photos–double no. You want your date to be pleasantly surprised when you are exactly as (or better than!) billed, and you can always explain on your first date that in order to outsmart the app’s algorithms you fudged your age by a few years. At which point, you may find out that he or she did as well. It’s something you can laugh about over vegan nachos and jalapeno margaritas. 

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Show all sides of yourself

If you’re looking to attract a three-dimensional man who has layers and interests, show him yours too. If you love skiing, show a pic of you on the slopes. If you’re obsessed with books, load a photo of yourself in a book store. Think about who you’re wanting to attract and put your interests out there, because no one wants to wind up with someone they have nothing in common with. 

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Gamify your love life

This is a “if you can’t beat ‘em join ‘em” piece of advice. If you try to take your life less seriously and treat this like a game of sorts, you might just have a little fun with it. Search women one day so you can see what other people’s profiles look like. 

If you’re not sure what you’re into or who you’re into, join a few different sites. Scroll through the possibilities. This is kind of like shopping at a sample sale. You may stumble across something off-the-beaten-path that tickles your fancy for whatever reason. 

Maybe someone makes you laugh, or writes something witty as a “hello.” Awesome! 50 is wholly experimental. Who are you outside of your work and your family? Internet dating is a great place to just try some different things out and surprise yourself with what you might be interested in at this stage of the game. Send a wink, give a virtual nod. Flirt a little. 

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See Also

Your profile is not a questionnaire you are filling out at the dermatologist’s office

So many people say they are “spontaneous” and “fun,” but then reading their profiles is about as exciting as watching paint dry. Mine was a spoof on the Californians of SNL, so I figured if people thought I was weird they would stay away, and if someone got me, then hooray for him! This seemed like a good way to avoid dates where we politely swirled the ice in our glasses struggling to make conversation and kicking ourselves for not setting the DVR to record “This is Us.

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Be safe out there

Don’t meet for a bloody hike in the middle of the woods! Don’t have this stranger pick you up for a date either. Do your due diligence. Google is your new best friend. If you’re on a first date and something feels off, it probably is. Listening to your instincts is a muscle you must flex. The more you lean into your intuition and learn to trust it, the better the odds you will be making smart decisions. 

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Marketing research

On your first dates ask what they liked about your profile. You can start to put together research for what is/is not working for you and tweak accordingly! 

Remember that dating, whether you meet online or through common friends or at a bar, is supposed to be fun. This is your journey. You make the rules and decide who gets to be part of your story. Some dates will become footnotes, others will be good for a laugh at happy hour with your friends, and some might be epic adventures that make your heart want things again.

What About Joining a Professional Matchmaking Agency?

“As we get older, we still have a need for companionship and intimacy – something that has been reinforced with the isolation of lockdown – and although the dating landscape may have changed since you last dated, dating in your 50s can be just as fun as it was in your 20s,” said Michelle Begy, Managing Director and Founder of Ignite Dating. Whether you are divorced, widowed or been single for a long time, finding yourself single in your 50s can be quite a daunting prospect – but it doesn’t have to be.”


The first step in any dating journey, regardless of your age, is to make sure that you are ready. Past experiences can massively influence your feelings around dating and relationships. You may find that after months of isolation, alongside the common worries of fear of rejection and feelings of guilt, that you now have the added anxiety about meeting new people in person. However, with the right support this new dating world can bring new ways to safely meet people.


“Understanding the difficulties that come with over 50s dating, a matchmaker can help you to navigate your dating journey and make sure that you feel confident, energised and safe at all times,” explained Michelle. “With on-hand support and guidance throughout the process, matchmakers can help you discover what you are really looking for in a partner and hand-select the right people to give you the best chance of achieving that ultimate goal of a long-term relationship.”


“It is important to be open-minded and realistic as to what you are looking for these days,” emphasised Michelle. “Those that are open-minded about what they are looking for, trust in the process and are honest with themselves and their matchmaker, will find that the dating journey is just as fun as it was back when they were in their 20s – only this time they are more confident in themselves, smarter, and understand exactly what they want from life and their relationships.”

This article was written by Rebecca Cullen for Kiiona Magazine

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