We recently connected with Susan Winter and have shared our conversation below.
Susan, thanks for taking the time to share your stories with us today Can you open up about a risk you’ve taken – what it was like taking that risk, why you took the risk and how it turned out?
Taking a Risk:
Risk comes in many forms—stepping into a competitive field, investing savings into a startup, or the unexpected risk of falling in love. The last one became my story.
Falling in love is a risk. It’s a straight up gamble with no guarantees. But what happens when your love is so unconventional it threatens your career and reputation? Most would walk away. I didn’t.
I arrived in New York City as an Opera singer and stage actress. The work thrilled me. The lifestyle didn’t. Over seven years, I transitioned to becoming a Corporate Spokesperson for over half of the Fortune 500 companies. That career led to becoming the host and moderator of ‘Corporate Profiles’ on Financial News Network (FNN), now called CNBC. The work was exciting and the respect fulfilling.
With my career came societal expectations about my romantic choices. People assumed I’d choose someone polished, cosmopolitan, and age appropriate. But when I built my dream home in a rural location an hour from Manhattan, my life quickly changed.
Suddenly living outside of the cosmopolitan New York City environment, I was exposed to a limited dating pool. Yet, it was there that I met a wonderful younger man in the local gym with whom I had great conversations. He was bright, ambitious, and a deep thinker. I had no idea that he would become my partner a year later and would mark the great love in my life.
In 1995, in a remote town, a relationship with someone 20 years younger was unthinkable—even to me. But when something feels true and right, you know it.
This wasn’t Manhattan, and I had no allies. As a newcomer from the big city, I sparked a storm of gossip and controversy. Invitations to community events dried up, and friends—both new and old—distanced themselves. Some women openly admitted their husbands forbade them from seeing me.
As rumors snowballed, so did the consequences. I was branded a “witch” and a “spellcaster.” Simple errands like getting gas or groceries became battles, with attendants sometimes refusing to serve me. My TV show on spirituality and higher consciousness, ‘Higher Ground,’ was pulled from the local network after over 100 residents signed a petition labeling me a “detriment to the community.”
That’s a long fall from being a highly respected business professional. But in that time and place— it was my reality. I could have capitulated. I could have given up. I could have dumped my boyfriend and been gradually accepted back into the group. But this was not a group from whom I wanted acceptance. And moreover, there was a greater conversation to be had.
I believe that Life is beautiful and purposeful in its events. Nothing comes here to torture us, only to advance us. And in the midst of all this drama and trauma, I held steadfast to that knowledge. It was a casual comment by a friend that enabled me to activate the greater gift within all of this pain. She suggested writing a book about older women and younger men.
That book became an international bestseller. ‘Older Women/Younger Men; New Options for Love and Romance’ (New Horizon Press, 2000) is still considered the ‘bible’ for older women and the younger men who love them. I interviewed over 200 couples who had similar stories to mine. Formerly ostracized, they now had a voice. Formerly misunderstood, they now brought forth a greater understanding of inclusion and opportunities for love.
The media attention I gained allowed me to uncover a new and unexpected career; that of Relationship Expert— a title given to me by ‘The Today Show.’
I didn’t anticipate being in this field as it didn’t exist at that time. And though I was one of the first, hundreds of others have since entered the dating and relationship realm. To date, I’ve counseled over 6000 individuals. I have over 41 million views on YouTube, and 1200 interviews by top-tier newspapers, magazines, TV, Radio, and Podcasts.
I had no idea that I would discover my true calling by taking the risk of falling in love. This type of risk isn’t associated with career success. And I had no idea that in the midst of all the tears and pain, I was actually on the correct path to discovering my greatest contribution and deepest happiness.
Here’s the twist. We rarely understand the process as it’s happening—its purpose is obscured by uncertainty.
To be sure, some risks aren’t worth taking. They’re a known dead end. But some risks “pull” at us, compelling us forward despite every outward sign to stop. It’s in those moments, when we’re driven by something we can’t yet name, that we’re honoring an inner truth—still forming, not yet born, but quietly coming into fruition.
As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
What I do:
As a Relationship Expert, I help people build healthy, happy partnerships. My main focus areas include Dating Games/Red Flags, New Relationships, Breakup Recovery, Self-Love, Relationship Advice for Couples, Communication Skills, Older Women/Younger Men, and How to Be Single and Happy. I also offer a collection of books, audiobooks, and digital products along with counseling services online and in person.
I’m fortunate to have a large international audience, built over 10 years of writing before becoming a coach and through more than 1,000 YouTube videos. Extensive media coverage has amplified my reach, allowing me to be seen and heard worldwide. I’m a regular contributor to international outlets, including BBC News, ITV News, TalkTV London, El Mundo, The London Times, Mumbai Mirror, The Irish Times, Bahrain Woman, Irish Examiner, and The Times of India.
What I’m proud of:
I’m most proud of my clients’ success, the majority of whom are now in loving, stable partnerships—married, engaged, or happily living together. I’m equally grateful for a devoted audience whose support and thoughtful commentary inspires me daily. It’s fulfilling to know that my videos and writing are helping so many, even those who aren’t clients.
I’m also proud of significant career milestones: my center stage interview on The Oprah Show and keynote addresses at the World Economic Forum (‘The Intersection of Digital and Emotional Intelligence’) and the International Mental Health Festival (‘How to Create Love À La Carte’).
Let’s talk about resilience next – do you have a story you can share with us?
Starting a new career later in life demands a unique kind of resilience. It’s not just about forging ahead, staying disciplined, or maintaining momentum—it’s about being willing to start at the bottom and climb back up. For those who’ve reached the peak of their former careers, it’s a daunting task to be a beginner again.
What’s a lesson you had to unlearn and what’s the backstory?
I had to unlearn the desire for social approval. Being at the center of controversy isn’t easy, but it’s far better endured when you’re fighting for a greater cause. The cause was beyond older women and younger men. It was about a woman’s worth—beyond youth and beauty. And the ability to be seen in totality, with inherent value that’s undiminished by time.
I prefer to be liked, as we all do. I prefer to be respected. What I never expected was the admiration and respect that came from being true to myself and my beliefs. But by playing the wildcard and trusting my gut, I found the ultimate form of guidance, and acceptance.
Contact Info:
- Website: https://www.susanwinter.net/
- Instagram: https://www.instagram.com/susanewinter
- Facebook: https://www.facebook.com/susanwinterrelationshipexpert/
- Linkedin: https://www.linkedin.com/in/susan-winter-033a433
- Twitter: https://twitter.com/susan_e_winter
- Youtube: https://www.youtube.com@SusanWinter
- Other: IMDb filmography page: https://www.imdb.com/name/nm12557601/?ref_=rvi_nm
IMDb bio: https://www.imdb.com/name/nm12557601/publicity?ref_=nm_pdt_pub_sm
https://podcasts.apple.com/us/podcast/the-susan-winter-show/id1041520404
https://music.amazon.com/podcasts/07dc0bd1-534f-4e0d-9c0f-e2f0a8452ba9/The-Susan-Winter-Show
Image Credits
Contact Page Headshot: Dasha Dare, NYC I certify that I have the rights to this headshot.