Stories of Women Dating in their 50’s and 60’s

Janine and Kevin

Janine and Kevin

Do you wonder whether you’ll ever meet a man who is the right partner for the woman you’ve become? Janine did. She’d left her quarter-of-a-century marriage. When the pandemic began eight years later, she had a successful career and the wisdom that comes from decades of self-development. On our Season 4 finale, Janine shares how she approached dating as an adventure, came close to giving up on her search, and took a series of remarkable risks that has led her to the love she was seeking.

Sandy and the Liverpool Dude

Sandy and the Liverpool Dude

How do you handle things when a date you’re excited to go on leads to the ultimate dating disappointment? Sandy knows the answer. She and the Liverpool Dude had matched on Bumble. They talked for hours on the phone and texted multiple times. There was a palpable connection. She said “yes” to a first date. Listen to discover what happened next.

Carolyn and Her Fifty First Dates

Carolyn and Her Fifty First Dates

It’s not unusual to date the same kind of person again and again, but Carolyn didn’t want to do that. Following a breakup, she decided to date a wide variety of types of men so that she could identify the qualities she wanted in a long-term partner. She named her adventure the “Fifty First Dates Project.” Find out what happened, what she learned during her two and a half year dating odyssey, and whether it led her to her Mr. Yes.

Cindy and Bob

Cindy and Bob

Bob had the background and accomplishments that Cindy thought she wanted in her next partner. He was well educated. He owned a ranch. He was financially successful. He also had a lot of drama going on in his life. Cindy, who was on the podcast in Season 2, has come back to delve into her first date with Bob and all that transpired afterwards. Season 4, Episode 8

Siobhan and Carl

Siobhan and Carl

Do you have a long-standing rule that you’ll never break? Siobhan’s was to only go on first dates in public places. When Carl asked her to his house for dinner for their debut date, the invite came after they’d talked almost nightly for over a month. She’d done her online sleuthing. She felt she knew a lot about him. She said “YES.” On our Season 4 premiere, we find out whether Siobhan was right to break her rule and all that took place after she did.

Chloe and David

Chloe and David

After her 24-year marriage ended, Chloe was unsure of her identity and purpose. With her kids now adults, she found the courage to move across the country and start her life anew. In our Season 3 finale, Chloe shares how she reinvented herself in her early 50s. She met David soon after the pandemic began, learned about herself as she got to know him, and ultimately recognized that she’s a badass.

Lexi and Jerome

Lexi and Jerome

Are you able to sense true chemistry and connection from texts, calls, and virtual dates? Or can you only sense true chemistry in person? Lexi returns to talk about her date with Jerome. After lots of phone conversations, she had already imagined a future with him. And then they met. Was she right? Find out.

Juliana and Dan

Juliana and Dan

When there’s not a pandemic going on, New Year’s Eve is all about celebrating with others. Juliana had a New Year’s Eve date with a man who talked a good game, but did he follow through? Listen to find out how she handled what happened.

Jamie and Barb

Jamie and Barb

Dating has slowed down because of the coronavirus. People are spending weeks or months connecting remotely before saying “hello” face-to-face. Jamie, who’s in her late 50s and hadn’t dated in years, chose to start again as Covid-19 was spreading. Barb and she chatted regularly for six weeks before making plans to meet. Jamie reveals what it’s like to return to dating during the pandemic and the silver lining she discovered.

Anne and Mike

Anne and Mike

Should you give a guy a second chance? That’s a question Anne asked herself when she and Mike reconnected five years after their work romance ended. Tune in to find out what happened when she decided to give their long-distance relationship a try again.

Lexi and Sam

Lexi and Sam

Some women know exactly what they want in a life partner. Lexi spent years running her successful company. With the little free time she had to date, she never wavered from the list of qualities she wanted in a soulmate. Was Sam the man she was seeking? Find out.