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Village Voice Article: 10 Brutally Honest Reasons You’re Still Single in Your 40s, 50s, and 60s—and How to Change That


Village voice



10 Brutally Honest Reasons You’re Still Single in Your 40s, 50s, and 60s—and How to Change That




September 10, 2024


By Top Dating Coach with 30 Years of Experience, Andrea McGinty of 33,000 dates and It’s Just Lunch


Let’s be real—being single in your 40s, 50s, or even 60s is a whole new ball game. In your 20s, relationships were often a no-brainer. You met people through school, work, or friends, and romance seemed to blossom without much effort. Fast forward a few decades, and dating can feel like trying to find a needle in a haystack.


But here’s the kicker: if you’re single now and don’t want to be, there are some brutally honest reasons why—and plenty you can do to fix that! So buckle up, because I’m about to spill some hard truths mixed with a lot of humor and encouragement. Ready?


  1. Inertia is Not Your Friend

You say you want a relationship, but are you really doing anything about it? Just like you didn’t become successful at work by sitting on your hands, you’re not going to find love binge-watching Netflix. You’ve got to get moving!


Photo of netflix

Netflix Courtesy of WBUR


Solution: Join an online dating site (no, not for pen pals), try new meetups, or volunteer—especially in places where you’re likely to meet new people.


  1. You’re a Bit of a Negative Nancy

Be honest: do you believe there are no good men or women left? If you think all men are taken, want someone younger, or that women are misrepresenting themselves online, you’re setting yourself up for failure.


Solution: Ditch the negativity. Adopt a “can-do” attitude for the next three months. Avoid that one perpetually single friend who complains about dating—it’s time for a positivity boost!


  1. Your Checklist is Longer Than the Constitution

If you’ve got a list of impossible criteria, you’re setting yourself up for disappointment. Chemistry, core values, and communication are the trifecta of what really matters. Want a bald guy? Hey, I was married to one for 24 years!


Solution: Be open to possibilities. You don’t need a carbon copy of your ex, or even someone with all the same interests. Differences are what keep things exciting!


  1. You’re Scaring People Off

Are you conducting job interviews on first dates? Relax, this isn’t a boardroom meeting—it’s supposed to be fun!


Solution: Keep the conversation light and easy. Save the heavy “what are you looking for in life” talk for later dates. Your goal on the first date? Get a second one!


  1. You Gave Up Too Soon

So you threw up a profile, slapped on a couple of pics, and then got discouraged when Mr. or Ms. Perfect didn’t immediately show up. Look, algorithms are your friend, but you’ve got to put in the work.


Solution: Commit to at least three months of strategic dating. Choose your platforms wisely, spruce up your profile, and stay patient!


  1. Let’s Talk Self-Care

You don’t need to look like a supermodel, but taking care of yourself makes a huge difference. A healthy glow and a great smile are way more attractive than you think.


Solution: Stay active, eat right, whiten those teeth, and for goodness’ sake, get a wardrobe update for your photos. Authenticity over AI, please.


  1. You’re Letting Low Confidence Sabotage You

Confidence is attractive—period. But if you’re struggling with self-esteem, that lack of confidence can be a massive turn-off.


Solution: Get out there! Say yes to dates you might be on the fence about. After a few good conversations, you’ll see your confidence soar.


  1. You’re in a Rut

Same old routines? They’re comfortable, but they’re keeping you single. Break free from the hamster wheel.


Solution: Shake things up. Try something new—whether it’s a cooking class, a walking tour, or a solo adventure. You’d be amazed at what you’ll discover about yourself and others.


  1. You Keep Dating the Wrong People

It’s easy to be attracted to what’s familiar, even if it’s not good for you. But dating a clone of your last ex is a surefire way to stay single.


Solution: Identify the patterns in your past relationships that haven’t worked, and consciously try dating someone who’s different. You might surprise yourself!


  1. You’re Forgetting to Have Fun

Let’s be honest: dating can be nerve-wracking. But if you’re not at least a little excited before a date, you’re probably doing it wrong.


Solution: Relax and enjoy the process. Whether it’s a good date or a bad one, it’s all part of the journey. With the right mindset, even awkward encounters can be entertaining.


So, What’s Next?


If you’re serious about finding love—or even just about having some fun on the dating scene—remember this: it’s not about luck, it’s about strategy. A positive mindset, the right dating site, and the willingness to try new things can make all the difference. I’ve seen love bloom for thousands of people over the years. Trust me, it can happen for you too.



About the Author

Andrea McGinty, a business entrepreneur and dating expert for over 30 years, founded the wildly successful dating service It’s Just Lunch in the ‘90s and has set up over 30,000 first dates. After selling the company to private equity, she knew what people needed in the 2010s and 2020s—a road map and dating coach to navigate all aspects of online dating. 33000dates.com is a strategic means to meeting people that is both effective and not time-consuming. She has a 65% success rate and over 7,000 marriages. Known for her no-nonsense advice, Andrea has helped thousands find love—whether it’s for a lifetime or just for a fun adventure. When she’s not coaching, she enjoys eating any and every cuisine and dessert, her new husband and three children, yoga, rollercoasters and sharing brutally honest (but helpful!) dating tips with her clients.




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