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Dating Over 50 | CrunchyTales

4 Mindset Shifts To Date Successfully When Over 50

4 min read

Dating over 50 can be terrifying, especially if you have been in a long-term marriage or relationship and then out of the game for a while. Many things have changed since you were last in the dating pool: social norms have shifted (women dating women, women dating men who used to be women, etc.). Social media, which essentially didn’t exist 20 years ago, is now almost a required filter for ensuring a prospect isn’t a serial killer. And dating sites, which back then were more taboo than “must do” and frequented only by the perceived “desperate” people, are now an integral part of the dating mix.

So, here it is 2022, and you find yourself suddenly single again (or still single). Dating now feels like you are a cat inside a fishbowl watching in amazement as all of the fishes swirl outside the bowl and you are trying to figure out where and how to fit in.

Thank goodness there are a few age-old mindsets that can help you successfully navigate the terrifying dating waters.

Mindset #1 Confidence is still a turn-on

When we were in our 20s and 30s and faced what seemed like an unlimited pool of eligible bachelors, confidence was much easier to come by. We flaunted our self-assurance like when one has multiple options – with abandon. Back then, the motto to live by was “Men are like buses. A new one comes along every 20 minutes.”

Now, suddenly in our 50s, the “buses” don’t run as often, and those that are running seem to be moving so much slower than they used to. Then there’s the fact that because many buses have been taken out of commission (death, marriage, prefer other men), there are now more interested passengers than there are buses. Dating is now more of a limited numbers game.

The best way to win is to stride into your closet and shake the mothballs off of your old friend “Confidence“. Slip her on again because guys find confidence sexy!

Think how much you stand out when you own the room confidently versus other women who shy away from being their authentic bold and beautiful selves. A woman of 50 knows what she wants far better than her younger self ever did. We’ve had the starter husbands. We’ve raised kids and excelled professionally. What isn’t there to be confident about?

So don’t keep your renaissance woman hidden. As author, Marianne Williamson says, “Your playing small doesn’t serve the world.” Let your light shine when you are around someone you feel worthy of it, and more importantly, someone you deem worthy of you. Own who you are with a smile. Confidence attracts attention, which is the first step to making a love connection, isn’t it?

Mindset #2. Neediness is still a turn-off

Neediness didn’t look good on you when you were younger, so it certainly doesn’t look good on a “woman of a certain age. A need for constant reassurance – “Did you miss me?” “Do I look fat in these jeans?” “Who was that you were talking to?” “Where is this relationship going?” – reeks of insecurity and self-doubt. Men can smell it a mile away. Those that are drawn to it tend to be experts at manipulating situations to their benefit because they know they have all of the power. Guys who are not attracted to neediness disappear without a backward glance. They’ve probably discovered by now that a woman who doesn’t love herself can’t possibly make a solid equal. If an emotionally-balanced, long-term relationship or marriage is what you are aiming for, identify areas that might make you feel insecure and work on those before launching your search for Mr. Right.

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Mindset #3. Always trust your gut

Trusting your instincts is still the best way to see beyond the pretenders, cheaters, deadbeats, and potential catfishers. By now, we have hopefully learned NOT to ignore that little voice inside our head which sends up warning flares when “something about that guy doesn’t feel right.” Lean into your spidey senses. It really is as simple as that.

Mindset #4. Be willing to be vulnerable

Being vulnerable is scary at any age. But it’s a necessity if you truly want to be in a healthy, monogamous, and committed relationship, especially after 50. Our bodies don’t look the same. Our sexual appetites and desires have been savaged by menopause. And our hearts have been mauled (or at least slightly battered) maybe more than once. Men we’ve dated have stood us up, lied about their marital status, or didn’t reveal their STDs or their six-month-old child and a wife who isn’t claiming the “ex” status! If we come searching for love while hauling all of our past negative experiences … whew! That’s a lot of baggage we’re carrying.

We travelled much lighter in our younger years. So the thought of sharing our experiences – the good, the bad, and yes, even the ugly – with a potential soul mate could shake us to our core. But if we tap into Mindset #1, we can handle sensitive topics and big reveals with more ease. We cannot make assumptions that all men are alike and therefore cannot be trusted. To love as if you’ve never been hurt before is the greatest mindset of all to reconcile on this journey. Leaning into your vulnerability may be just what the doctor ordered if it’s true love you are seeking.

Before going on your next date or embarking on your quest to find true love, begin with the end in mind – Love yourself first and foremost. It’s all an inside job that begins with mindset. Enjoy!

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About The Author

Cheryl Grace | Lifestyle Expert

Cheryl Grace | Lifestyle Expert

Cheryl Grace is the CEO and founder of Powerful Penny LLC, an executive coaching, consulting and lifestyle firm that provides empowerment resources, online courses, workshops, and executive coaching services. A former SVP at a global corporation, Cheryl has refocused her work from successfully transforming corporate reputations to transforming individuals striving for next-level advancement. She has been seen on Daytime Chicago and CBS This Morning. Additionally, Cheryl is a 2022 Women of Color Innovator Awards recipient, has been profiled in Essence and Forbes, and has been named one of Black Enterprise Magazine’s “50 Most Powerful Business Women,” a “Remarkable Person” by the Chicago Tribune, and a “Distinguished Alum” by Purdue University. Signup to receive Cheryl’s Level Up with Grace Newsletter.

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