Dating After 40 with Grace and Grit

by | Jun 3, 2024 | 0 comments

Love Is Possible Over 40, 50, 60 and Beyond

Real talk… dating can be nerve wracking at any age. And, navigating the dating scene after 40 feels like sailing into uncharted waters. It comes with its own set of insecurities, especially when you’re flaunting a new crown of silver strands. In a world that often equates beauty with youth, it takes a big dose of confidence and a sprinkle of humor to flip the script, showing that gray hair isn’t just a sign of aging—it’s a badge of honor. It tells tales of wisdom, experience, and unabashed self-love. 

The Silver Lining: Embracing Gray Hair

Society is finally catching up with the idea that beauty isn’t “one size fits all,” and the range of colors our hair can turn is as natural and as stunning as a sunset. Icons like Andy McDowell and Tia Mowry are not just rocking their grays; they’re leading a movement that redefines attractiveness, showing that silver is sexy!

The Dating Game: First Impressions and Confidence

First impressions in the dating game are crucial, but they should never come at the expense of your authenticity. Dressing for a date when you’re proudly wearing your natural hair color is about balance—highlighting your best features with a touch of personal style that says, “Yes, this is me, and I’m fabulous.”

Fashion and grooming tips? Go for what makes you feel confident and comfortable, be it a classic little black dress or something that speaks to your bohemian spirit. The key is to wear your gray hair like the crown it is—unapologetically and with grace.

Online Dating and Gray Hair: Navigating the Digital Realm

Your online dating profile is your digital introduction to potential matches, and yes, it should absolutely reflect the real you—including your gorgeous gray locks. Choose photos that showcase your natural beauty and the joy that comes with it. When writing your bio, be honest and upfront about who you are. Remember authenticity attracts authenticity.

Engaging in conversations online can be daunting, but truthfully, the person on the other end is looking for connection just as much as you are. Be genuine, be curious, and don’t shy away from sharing your journey to silver—the challenges, the triumphs, and everything in between.

Real-Life : Successes and Challenges

If I am being honest, my transition to gray was a decision that took me a long time to come to terms with.  But, I decided that I could always change my mind and go back to coloring if I didn’t like it.  In the beginning, I got gray braids and it gave me an idea of what to expect. Once I saw the potential, I was all in! 

At the time I began transitioning, I was dating my now husband. I know that deep in my soul, there was some level of nervousness that I grappled with because I didn’t know myself as gray, and I was asking someone to follow along with me on the journey.  It was intimidating, but he was a huge support. 

Recently, we were talking about his thoughts on walking this journey with me, and he got real candid about his feelings. You can watch our discussion about it HERE!

Conclusion

Ladies, if there’s one thing to take away from this, it’s that your silver strands are not something to feel self conscious about; they represent the most authentic version of you. They tell the world that you’ve lived, loved, and learned, and you’re not afraid to show it. In the dating scene, this confidence and self-acceptance can be your greatest ally. Walk tall and proud because girl,  you are gorgeous!

Remember, whether you’re stepping out for a first date or curating your online dating profile, do it with the confidence of someone who knows their worth and isn’t afraid to show it. Your silver hair isn’t just a sign of aging; it’s a symbol of your unique story, and the right person will love you all the more for it.

Ready to join the movement and celebrate every silver strand? Follow me on Instagram @FlyGrannyBk and don’t forget to subscribe to my newsletter at www.flygrannybk.com for more stories, tips, and a community that celebrates authenticity and the beauty of aging gracefully.

Here’s to finding love, laughter, and a whole lot of adventure after 40. 

The best is yet to come!

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This is the last weekend of 2025! Wow that went fast!
Posting this to say I’m grateful for everything that 2025 brought, including you, my dear followers and friends- although I don’t see many of you like I did in the old IG days around 2020-so if you’re seeing me for the first time in a long time drop a Hello below!
I’m wishing you everything you wish for yourself in 2026, and above all, I wish you good health and blessings now and always!
Cheers!
#styleover60#over60andfabulous#silversister #endoftheyear
Merry Christmas from our house to yours! Thank you for stopping by.
Just a reminder that Christ Jesus is the reason for the Season, and gave us the greatest gift of all-eternal life.

“For unto us a Child is born,
Unto us a Son is given;
And the government will be upon His shoulder.
And His name will be called
Wonderful, Counselor, Mighty God,
Everlasting Father, Prince of Peace.”Isaiah 9:6

“And this is the testimony: God has given us eternal life, and this life is in his Son.”
1 John 5:11

#christmas2025#ᴊᴇsᴜsɪsʟᴏʀᴅ#christmasfamilyportrait
Brooklyn, early 1960s.
Four years old. Wide-eyed. Holding court on Santa’s lap like I had a list and opinions.

This was likely downtown on Fulton Street, at the old A&S — back when department stores felt magical, Santa felt real, and Brooklyn at Christmas had a hum you could feel in your bones. The giant Christmas tree near the elevators, and there were so many people shopping you could barely move! The kind of place where moms dressed you up, dads waited patiently, and the city felt smaller, safer, and full of promise.

I can almost smell the waffles in McCrory’s, hear the street noise outside, feel the excitement of being seen and remembered. A little girl in a big city, already soaking it all in. These are the moments that shape us — before life layers us up, before time speeds ahead.

Proof that nostalgia isn’t just memory… it’s feeling. And some of it never leaves you.

Brooklyn raised me. Christmas held me. And that little girl is still right here.
#childhoodmemories #throwbacktuesday#VintageNYC #BrooklynHistory #ThenAndNow

Brooklyn childhood, 1960s Brooklyn, vintage Christmas, old New York, Fulton Street Brooklyn, A&S department store, Brooklyn nostalgia, retro NYC, classic New York Christmas, Santa memories, growing up Brooklyn, New York childhood, vintage holiday memories, timeless moments, then and now, Christmas in the city, mid century Brooklyn, family memories, Brooklyn history, little girl in New York
Took my best Bud Rocky downtown for a stroll…
Stay tuned for more pics of Rocky.

#schnauzersofinstagram #mansbestfriend #holidayvibes #whitedogs#whitehair

Mini schnauzer, white dog, dog walking, Christmas downtown, style over 60
Welcome to my Mini Amazon Holiday Haul…
I am owning the fact that my figure is a little Rubenesque these days as I have packed on a few pounds, but I’m owning my sexy curves, and I’ll work on my weight again…ahem…after the holidays!
Erybody outchere gettin’ skinny… but not me!!! Don’t worry, I’ll be back!
Amen to Body Positivity for the season, in my newly redesigned kitchen I might add!

Meanwhile, check these out:
1. Sparkle dress
2. Sparkle top
3. Sequin dress

Do you have a fave on me? Let me know in the comments below.

You still have time to ring in the New Year!!! Affordable and Chic!

Comment HOLIDAY below to get a DM with the link to these items in my Amazon Faves Shop!

(***Franco Sarto Teal booties are 2 years old and might be hard to find)

#holidaystyle#styleover60#over60andfabulous#sexycurves

Holiday style ideas, amazon haul, affordable luxury, outfit ideas, winter weight gain, body positivity, fashion finds, sequins, sequin dress, women over 60 style, holiday inspo, curvy woman, mature woman, sparkly style, rubenesque body, sexy mature, stylish woman
5-step routines? Couldn’t be me 🙅‍♀️ @fieracosmetics MoistureWiser™ keeps it simple, hydrated, smooth, primed, and ready in one step 💧✨  😉 Click the link in my bio for a special discount and goodies

#Fiera #Sponsored
Filipino food in my neck of the woods!
Who woulda thunk it? Luiza’s just opened out here in Prescott Valley, AZ just yesterday, so I had to try it.
Dave liked it, it was good, but my mother’s from  Pampanga, so I’m a bit spoiled. IYKYK 
We welcome the food diversity! What’s next-Soul Food? Jamaican Food? Dominican Food? Hope so!!!

#blackandfilipino #filipinofood #pinoy #blasian#foodies

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