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Heart's Encore

Powerful Penny LLC founder, Cheryl Grace, has become the go-to source destination for real talk, real strategies, and real results when it comes to love and dating over 45, with her Heart's Encore blog.

Whether you're diving back into the dating pool, looking to reignite the spark, or just want to navigate relationships with more confidence, Heart's Encore has you covered. Get ready for honest conversations, expert insights, and a little fun along the way!

Heart’s Encore is your go-to destination for fresh insights, expert advice, and a little bit of fun. All designed to help you find, keep, and enjoy love at this stage of life.

📅 Check us out every Friday (date night) for engaging insights and even conversations and strategies that break dating myths, unlock new relationship possibilities, and give you the tools to navigate love with confidence.

✨ Stay in the know!

Here, you can:

âś… Get a sneak peek at upcoming topics
✅ Take fun & insightful quizzes—like your Dating Mindset or Flirting Style
âś… Access exclusive tips and resources to elevate your love life


💡 Check back every week for updates, because love doesn’t come with an expiration date, but relationships that don’t align with your values and needs absolutely should.


      Meet Heart's Encore 

Relationship Coach

I help high-achieving women stop wasting time on relationships that are never going anywhere by teaching them how to recognize alignment, own their standards, still have fun, and embrace their inner girly girl.

Why Love? Why Now?

 Love doesn’t come with an expiration date! Life expectancy has increased over the decades, with many Boomers expected to live well into their 80s. Whether you're diving back into the dating pool, rekindling the spark, or figuring out what you truly want in a partner, Love Encore is here to guide the way.

If you're 45 and over, you know relationships hit different in this stage of life—more wisdom, less drama, and a whole lot more intentionality. So why now? Because there’s no better time to get the love you actually deserve.

Take our fun quiz to find out your mindset when it comes to love and get ready for real talk, real laughs, and real love— on WVON with Matt McGill and Powerful Penny Founding CEO, Cheryl Grace!

TAKE THE QUIZ

Meet Heart's Encore Hosts

✨ Charismatic, adventurous, and the definition of a confirmed bachelor, Matt McGill has established himself as one of the country’s premier radio personalities.

✨ A literal Prince Charming—minus the wedding bells—Matt brings his sharp wit, authentic male perspective, and unapologetic honesty to Love Encore.

✨ His engaging take on love, dating, and relationships keeps both men and women tuned in, offering the perfect counterbalance to Cheryl Grace’s relationship wisdom.

✨ With Matt on the mic, every episode is guaranteed to be a lively, insightful, and sometimes hilariously real conversation about love after 45!

✨ Powerful Penny Founding CEO Cheryl Grace knows firsthand that finding love after 45 is not just possible—it’s downright fabulous.

✨ She was over 50, and her fiancée over 60, when they married in a wedding that Chicago is still buzzing about. Since then Cheryl has made it her mission as a coach to help others find their own “happily ever after.”

✨ She’s more than a love coach; she’s a relationship game-changer. Through her vibrant personality, real-world advice, and proven strategies from her relationship boot camps and 1:1 coaching, Cheryl empowers her clients to go from "forlorn" to "fiancée." Offering practical tips, inspiring stories, and actionable insights that help clients of all ages reignite their love lives, navigate dating, and build lasting connections.

 💕Is Your Mindset Helping or

Hurting Your Love Life? 💕

Dating over 45 can be exciting, but your mindset shapes your experience more than you realize!
TAKE THE QUIZ
TAKE THE QUIZ

Are you open to new possibilities, or are you unknowingly holding yourself back?

Take this fun, eye-opening quiz to discover if you’re:

an Open-Minded Optimist

Hopeful but Hesitant, or

a Closed-Minded Cynic

when it comes to

TAKE THE QUIZ

Finding love is NOT just for the lucky—it’s for those who DECIDE to make it happen. 

Every Friday, we'll keep you connected to everything you need to know about love, dating and relationship trends.
THIS WEEK:

✨ Starting Over: Ghosting, Benching, and Breadcrumbing - Modern Dating Challenges

Modern dating comes with new challenges—ghosting, benching, and breadcrumbing can leave you feeling lost and frustrated. Cheryl breaks down these dating trends, helps you recognize the red flags, and offer strategies for setting boundaries and protecting your heart in today’s dating world.

Finding love is NOT just for the lucky—it’s for those who DECIDE to make it happen. 

Heart's Encore will keep you tuned in to everything you need to know!
EPISODE 2:
MARCH 14TH, 2025
2:00 PM CENTRAL


✨ Starting Over: Ghosting, Benching, and Breadcrumbing - Modern Dating Challenges

Modern dating comes with new challenges—ghosting, benching, and breadcrumbing can leave you feeling lost and frustrated. Matt and Cheryl break down these dating trends, help you recognize the red flags, and offer strategies for setting boundaries and protecting your heart in today’s dating world.

PAST BLOGS

Love, Leadership, and Life—It’s All Connected

 
Powerful Penny LLC is a leadership development and executive coaching company that believes success isn’t just about what you do for a living—it’s about how you show up in every part of life. That’s why we take a holistic approach to coaching, helping people find balance at work, in love, and at home.

The same qualities that make someone a great leader—confidence, communication, emotional intelligence, and clarity, are just as important in love. That’s why Heart's Encore is a natural extension of our work. Success in any area of life isn’t about luck, it’s about intentionality. And when you’re intentional, you create energy that carries into everything you do, bringing balance and making life work better.

Through executive coaching, change management, and conflict resolution, we help our clients navigate challenges with confidence, build stronger relationships, and create a life that feels as good as it looks on paper. And when people are happy and balanced, the companies they work for win too, with higher engagement, stronger teams, and better retention.

Whether you’re an employer investing in top talent or an individual ready for your next level in leadership—and life— we have programs and services designed to support your growth.
TAKE THE QUIZ