In this episode of Sixty Plus Uncensored, I dive into a subject that so many listeners have been curious about: how to find love and companionship later in life. My guest is Cheryl Maida, a professional matchmaker with more than 15 years of experience helping clients build meaningful and lasting relationships. Her insight into dating after 60 is refreshingly honest, practical, and full of real-world wisdom.
Who Is Cheryl Maida?
Cheryl didn’t set out to become a matchmaker. She began her career as a corporate recruiter, connecting professionals with new jobs. It was her father who suggested that the skills she had honed in interviewing and recruiting could easily translate to matchmaking. At first, Cheryl resisted the idea, but within a week she had ordered business cards and started meeting clients in coffee shops across South Florida. What began as a one-woman effort quickly grew into a thriving business, and today Cheryl works nationally under the Matchmaking.com brand.
A Fresh Approach to Dating After 60
Unlike online apps that focus heavily on appearances and quick impressions, Cheryl builds her introductions around lifestyle, values, and relationship goals. She believes that successful matchmaking is about more than just who looks good on paper. It is about understanding whether someone is seeking marriage, long-term partnership, or companionship, and ensuring that their expectations are realistic. Cheryl is also not afraid to turn away potential clients if their goals don’t align with what she can deliver.
Companionship and Romance in Later Life
One of the most fascinating parts of the conversation was Cheryl’s perspective on the difference between companionship and romance. For some people in their 60s, 70s, or 80s, finding someone to share dinners, movies, and travel with is the priority, while others still place a high value on intimacy. Cheryl helps her clients identify what truly matters to them so that the people she introduces are aligned from the very beginning.
Coaching Clients Toward Success
Cheryl’s work goes far beyond arranging introductions. She actively coaches her clients, offering constructive feedback after each date. Sometimes that means reminding a man to walk his date to her car, suggesting a client tidy up before picking someone up, or advising a woman to dress appropriately for a certain venue. These small but meaningful adjustments often make the difference between a single meeting and the start of a lasting relationship.
Success Stories That Prove It’s Never Too Late
Cheryl shared stories of clients in their 60s, 70s, and even 80s who found love through her service. Her success rate is over ninety percent, and she has seen everyone from widowers rediscovering companionship to retirees embarking on new adventures with partners they met through her introductions. Her work underscores the simple truth that it is never too late to build a new chapter filled with love and connection.
Practical Advice for Those Seeking Love
Not everyone will choose to hire a matchmaker, and Cheryl was quick to share practical advice for those who want to take matters into their own hands. She encourages people to get out of the house, tell friends and acquaintances that they are open to meeting someone new, and spend more time in places where meaningful connections can happen naturally. Even something as simple as smiling and making eye contact, she says, can open doors.
Why This Episode Matters
This conversation with Cheryl Maida is full of real-life stories, straightforward advice, and a reminder that life after 60 is far from over. For those who are single and wondering if it is still possible to find companionship, this episode offers both inspiration and practical strategies. It is a testament to the idea that love has no expiration date, and that the courage to put yourself out there is often the first step toward a richer, more fulfilling life.