My Flirtatious Fifties: Recent Episodes

Gay Stephenson

I had never really dated. I met my husband when I was 16. When we divorced, I jumped into a new relationship as soon as my heart healed. Becoming single again in my 50’s, I wondered if I’d ever love or be loved again. Was sex something I wanted? Would men find me attractive? Could I fall in love? Honestly I wasn’t sure. But I knew that I had to find out. Join me on this journey of discovery... starting with a holiday and the man I met by chance on the beach. Being flirtatious is something I embrace now although dating in Covid times is a toughie.

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He was playing to a packed room filled with dancing and joy. When the set was over, his friend introduced us. I was sweaty and glowing from dancing. He was barely off the stage. As the bass player’s eyes met mine, there was such a playful, deep, and magnetic intensity. I was overcome by the wild and powerful connection. Everything that happened after that was inevitable.


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We met in a bar in Vancouver. He was jet lagged, just off a flight from Germany. But fatigue didn’t stop him from making a move. “I’d like to take your photo” he said. And then he asked me out for dinner. This is the story of the photographer’s kiss... and more. Meeting people doesn’t always come easily. I’ve struggled to feel at ease. Have you? Would you like to date? Dating Expert Shanny Tebb of Shannyinthecity.com joins us! Despite COVID, “Dating and romance is not canceled!” she assures us, sharing tips and strategies that you can use right now to safely date and meet people, during a pandemic. Shanny is a boutique matchmaker and lifestyle coach based in Toronto. Follow her for daily tips on Instagram and Tiktok @shannyinthecity


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He offered me a taste of his pecan pie, then a bike ride through the countryside... our day ended with a romantic dinner by the river. But his tattooed body and his sensual touch would keep me awake deep into the night.


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A tall Frenchman catches my eye at a dance party and leads me down the cliffs, wine bottle and blanket in hand. The Arabian Sea is as dark as the sky and I feel I’m being swept away by the magnificent views, the wind, and the rhythmic crashing of the waves. But this evening goes awry and I end up in a scary situation.


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I met Yoga Man on Kundli Beach. He was perhaps the most talented and devoted yogi practising on the beach. He introduced himself to me offering me advice with my postures. Each day his greetings became more and more intimate but I already had a lover in Kundli... I also answer a listener’s question: Why did I move from Toronto to Vancouver?


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The day after we first met, the Man with the Plaid Hat took me on the back of his bike, to a secluded beach. He built us a sun shelter. Tucked inside and lying on sarongs in the sand, he spends hours caressing me and kissing me very slowly. My body is vibrating with desire and I long for the beach to empty so that I can be completely alone with him.


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Wild and Gentle Man found me in a restaurant, our eyes playfully inviting one another to make contact. He showed me hidden things about myself and touched me with his sweet texts. —— This episode meet my friend Tina! We were both new at solo travel when we met in Honduras. Listen as she reveals her motivation and inspiration for travelling alone for the first time in her forties. I’m so grateful to Tina for joining me on this episode and sharing her personal experiences and perspectives. We’d both love your feedback on this or on any episode.


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Riding the beach roads in Goa, India on the back of a motorbike, holding on to Midnight Rider, snuggled into him for warm, while whispering to each other about life and love was one of the most exciting and romantic moments of my life.


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The thrill of meeting Tall Dark and Handsome twice, totally by chance and the after midnight rendezvous that followed. I never imagined doing this, living these moments. It wasn’t love but damn it was exciting.


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I met my first lover after the breakup unexpectedly, walking on a beach. It was cold, I was wearing weird layers of yoga clothes. But somehow none of that mattered. This is the first episode of My Flirtatious Fifties, my journey of opening my heart to new adventures and living life!


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