Dating Over 50

Dating Over 50


Singles advice guru Marnie Macauley has humorous and savvy solutions for singles over 50 who are looking for love in all the wrong places.

Dating Over 50

My Dear Singularians,

Those of you who are in your 20-40’s are lucky. You know the games, the words, and how to use all the apps on your iPhone. For those of us who are older, we can feel like cave people as our grown children reinforce how we’re totally out of it.

Many so-called boomers — people born between the years of 1946 and 1964 — are entering singlehood later in life, holding onto the rules and values from the 1960s and 1970s. Yes, I know. The “new” 90 is 50, and the “new” 50 is 35 but we’ve earned those wrinkles. To quote Shirley Valentine, starring my good friend Pauline Collins … it shows we have experience.

Still, a society run by tweenies with tats does its best to cast aside anyone over the age of 40. PSHAW. I’m here to tell you it’s not over yet! We’re thriving, often with gelt, a history of love and commitment … which makes for an entertaining evening, if not a romance. Let’s look. (And for those who value experience, enjoy!)


Dear Marnie: I’m 53 and a single mom after a divorce. I’m very attractive, educated, a professional and look about 45. I’ve dated what I’ll call “spottily” in the seven years since divorcing — sometimes with passion, sometimes with malaise — and it just doesn’t do much for me. I’m beginning to feel that based on our society’s values, I have little to offer a man. I’m in that “invisible” group. I’m not in child-bearing years; I’m not in a help-him-get-ahead age; I don’t need him to support me; I’m not seeking a father for my child; I am often more worldly and traveled than the men I meet.

I have been asked out recently, but find that most men I meet are immature, self-centered, have unhealthy habits, lack awareness of why their marriage went wrong, or desire those things I can’t offer. I’m interested in connecting with someone, but have been feeling that the love I had (and I did experience real love) was my one experience with it and it’s over for me on that score. Any advice? — Dating at 53

MARNIE SAYS: Hey you adorable pessimist, if you don’t get that brilliant head of yours out of that supine position, I’ll have to personally whoop you into shape. On second thought … I will!

Getting It! Your Personal Strategy:

* You’re age-duped, angel. And worse, you’re letting the hype-meisters get to you. Trash any magazine featuring pencil-size tweenie people on the cover.

* Listen carefully and repeat. (UPBEAT) “I look terrific! I’m educated, professional and financially independent! I’m not wiggy about reproducing or looking for a daddy for my child — or myself! I’m worldly, sophisticated, not into it for the money!”

* Hear it with a different tone? Angel, you’re a better catch than Moby Dick! Need proof? How many men over 50 with an IQ higher than an eggplant would prefer an undereducated, money grubbing desperate damsel who has registered her biological clock with Timex — or a trophy? (OK, some, but not all.)

* You’re lying to yourself. You said you’re invisible. Invisible people don’t get noticed. You do. And you’d get more noticed if you’d repeat the above sentences like a mantra. Believe, honey, believe.

* Dating Rules for the Sophisticated: Clearly the boors you’ve been breaking bread with have gotten all tangled up with your self-image. So …

ONE: Take a man break. Don’t look at them, think about them, or man hunt for one month. Get in touch with you, you glorious thing, without worrying about “invisibility” or a dirty rotten scoundrel of a culture.

TWO: Do museums, trips, books, films that celebrate our gender. Rent “Shadowlands.” Honey, I have it on good personal authority that Joy Davidman was so ugly she could put Cruella deVille out of business, yet she captured the heart of the curmudgeonly old misogynist, C.S. Lewis. Then there’s Wallis Simpson who, at 51, almost took down England by wedding Edward. When you’ve finished this exercise, you’ll not only be (rightly) nuts about you, but cheered and emboldened by some glorious reality.

THREE: After the month, do NOT accept a date with a man until you’ve had at least three phone calls that don’t involve: a) his ex, b) his therapist, c) his 12-step program, d) massive boredom. This simple rule will spare your dreams (and your ear) not to mention the wear-and-tear of a night out with a waste of your time. Before you agree to share a latte, make sure he’s sweetness itself — and that he knows Philadelphia doesn’t start with an “F.”

FOUR: Keep the love affair with you going. Go where you want, do what you want. You’re attractive, free, and independent. Find your passion on your own terms. Once you get in passion with you, you’ll attract like-minded pursuers.

I promise that once you flip your “sorry” credentials into truth-mode, quit buying into idiot cultural notions or wasting time with idiots you’ll not only feel visible, but the halo of bright light surrounding you will grab the attention of the proper potentials.

P.S. Check your hormone levels, if you already haven’t. Sometimes a professionally prescribed medication boost can be a helpful mood-switcher.


Dear Readers: Getting back into the dating world when you’re 50 plus has always been daunting. But when our new “American idols” are barely pubescent with thighs the size of Q-tips, (or pecs the size of melons) who wouldn’t feel they’ve been banished to the Isle of Botox?

Of course, the absolutely terrific news is that our guys are there. Yup. That isle is filled with like-minded, marvelous singles over 50 who are desperately seeking a mature, compatible human who knows that the Chicago Seven isn’t a rap group.

Feh! You say? I can prove it. I received a ton of mail from seemingly amiable gentleman who, sputtering how they “normally wouldn’t do this,” were eager to meet our Ms. Invisible. While I don’t run a dating service, it confirmed that men of substance do exist for Baby Boomers plus. As with all else, the journey starts with us.

Getting Someone! You’re Personal Over-50 Strategies.

* First, forget about “finding someone – else.” Seventy-five per cent of the issue is about finding you. True, you’re bound to meet bounders and nit witches at any age in the dating jungle. But after 50, we’ve taken a few bumps and lumps. We’re sore, we’re raw. Go one step beyond the “Where are they?!” and the truth about ourselves will surface. Listen …

ONE: “I don’t really go out because I can’t stand the thought of another lousy date — or rejection! I’ve had enough.”

TWO: “I was so hurt and betrayed by my ex! I just don’t trust men.”

THREE: “If only I lost 50 pounds, that thigh waffle, had Botox…” And we sneak back into the sofa of safety, instead of facing down our demons.

* Finding you first is one of life’s golden experiences. Let’s get started.

First: Listen to your inner voice. What messages are you sending to yourself? Write: “I feel I am … ” and finish it ten times quickly. Is the concept of “loser” a theme?

Second: Challenge the myths and rotten assumptions about yourself. They’re lies told to you by other people — even parents — who were passing along their own craziness. Counter each self-defeating thought with evidence and re-framing. For example: I frequently get e-mail signed “Loser” from women, divorced after many years, when hubby turned into Brad Pitt with a bad toupee, and found a JLo clone. We can choose to see our rotten choices as a major life flop and drown our egos in self-recrimination, or … we can choose to see those years as a series of major successes thanks to our superb intentions.

Third: Tell yourself, for once, it isn’t about anyone else. I finally have the opportunity not to fix, bandage, or Neosporin a relationship. For once … this can be about me. What I want? What I need? Define it. Expect it. You know more about what works for you and what doesn’t. Make YOU the priority in your search.

* Quit expecting it to be easy. It takes patience. Guts. Chutzpah — and a plan. Get off the silly sofa! Unless you’ve connected with your mailman, or you’re expecting your love to bungee jump through your chimney, you’re not going to find him or her if you’re picking lint off your loveseat.

Now that I’ve got you interested … check out my proof that “they’re” out there.

Dennis writes: “Hi Marnie. I have trouble finding women of her caliber. I’m a 52-year-old man who has embarked on a second career in law school. I am well-read, traveled, and educated. It is too bad people like us cannot seem to get acquainted.”

Tom adds: “Well, this is a first for me. I am 58, can still feed myself, do not drool, and have a deep passion for living. I have not been looking for women because I really don’t go wherever it is that men look for them. I am well-educated, have been a teacher of literature for over 35 years, love good films, good books, politics, interesting conversation, and laughter. Yet, I feel invisible. An intelligent, witty and independent woman is exactly the kind of woman I would want to date. I wonder what your advice would be to a man who wants companionship, wants to share the beauty and absurdities of life with someone, but who doesn’t go ‘out there’ looking?”

And then there’s Craig: “This might sound very silly to you, but I have been single for 9 years and would love a competent, mature, woman. HELP! MARNIE THE MATCHMAKER … Hmmmm?”


Marnie: I’m 54, educated and am vice-president at my company. I’m told I’m witty with a great sense of humor. I love gatherings where I can meet new people. I’m average looking, loving and will open up with a woman when we get close, yet, I’m invisible.

The last two women decided after several dates, that I wasn’t right for them. The first is a college graduate with a well-paying job. But her last two lovers were losers. The first cheated and the next was a jobless drunk. She found them exciting and liked the drama. She finds me boring because I don’t have any major “problems.” What?

I should be glad it didn’t work out. OK, you’re probably right! Enter the next. Her friends said she was looking for a nice guy. So what happened? She decided she could not handle someone who treated her with respect, gave her compliments, was interested in what she thinks and says. She wanted a guy that was a hard to get, a macho type. So what’s going on here? I’m choosing the wrong ones?

OK, you tell me where the good ones are. And don’t even think about saying: get involved in volunteer organizations, quit trying so hard, go get therapy. I’ve tried all that. Oh yeah, the shrink says I would be a great catch for some lucky lady. I don’t go into a dating situation with a chip on my shoulder or baggage. I’ve been married before, so someone found me lovable, at least for 12 years. I pray every night it’s not over for me on that score, but it doesn’t look good out there in relationship land. What’s going on? Please give me words of encouragement. All I want is to love and be loved. Is that impossible? — John

MARNIE SAYS: Geez John! Where’s that “great sense of humor” when you need it? Two dates with women whose romance A-list includes Moonshine Man and Mystery Man and you’re already doom-glooming it? Listen up, my VP, you didn’t get there by moaning. No. You looked at a problem. Update your approach and take action. Don’t lose those qualities when you need them most.

Getting It! Your Personal Strategy:

* Update. You’re not 18. You’re 54! All the media hype is a fraud. Get it. Indeed, the so-called “perfect” 20-ish female is often a divorce statistic.

* Hope vs. Hype: I’m sure you’ve discussed this sorrowful state of affairs with your friends. I assure you, 90 percent of single women over 35 talk about it with theirs. Hear the echoes wafting? There’s a lotta great ladies out there, my man, who are gorgeous, un-needy, and ripe for a real relationship.

* If this were a project for your firm, what would you do? Dating is much like a business. Just as you would evaluate a job candidate, evaluate the truth about how you feel about the women you meet. I can tell you, trust is a huge issue among us oldies. So, are you trustworthy? Is she? Attend to the early signs. List them. If your instinct says “RUN” – run! If she’s a doll, hold her close and learn more.

* OK … the biggie. Where to find them. The answer? Everywhere. (Sometimes I think singles are on parallel universes, calling to each other in the night like Chloe and Daphnis). For heaven’s sake, casting directors do more work looking for the right extra! Remember, this is a work project, where would you look? Well, around you is a start. If you see a prospect that intrigues you, stop, talk. (Don’t scare her. Notice her.) One of my best friends, a widow in this 80’s found his love when he went to get a heart exam. She’s a doctor. They’re in wild, passionate love. It’s there, guys. Go where you enjoy. If you love opera, chances are if a lady’s there alone, she does too. Ask everyone you know (who likes you).

So, go, go, go. You’re just beginning the fascinating, sometimes frustrating journey. But, my witty, outgoing nice friend … I promise you. Keep heart, and you’ll find an open one.

And by the way, my number is … ask my darling editor!

Copyright © Marnie Macauley / 2014 Singular Communications, LLC

Marnie MacauleyAdvice guru Marnie Winston-Macauley — therapist, author, speaker — has been a radio, TV, and syndicated advice columnist and counselor for over 20 years. Witty, wise and totally irreverent with a self-professed loathing for psychobabble, she’s written over 20 books and calendars, along with  hundreds of relationship columns and features for prominent publications.  She has her MS degree from the Columbia University School of Social Work.  In media, her work has garnered her Emmy and Writer’s Guild Best Writing nominations. She is widowed and now living single. For personal advice, you can also find Marnie Macauley on or on Presto Experts. She invites you to join her on Facebook, Twitter, and LinkedIn. 
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5 thoughts on “Dating Over 50

  1. What was the cause for the divorce for 53 year old’s gift to humanity? She talks, or should I say brags, about herself like there is nothing wrong with her. The people in it aren’t perfect enough for her. Sounds like she has a real problem.

    1. Hi, and thanks for writing! The thing about writing columns is you try to pull some general principles, as you never know exactly what went wrong. For example, she may have sounded as if she were bragging, but perhaps she was just explaining that she’s got a lot to give someone.

      So, (ORGAN SWELLS) we don’t get the details — or the ending:)

      Singularly yours, love, Marnie

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