Women Dating Stories by Age

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

ByJodi Klein

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

ByJodi Klein

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

ByJodi Klein

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

Erin and Sara

ByJodi Klein

The saying “timing is everything” definitely applies to dating. Comedian Erin Foley’s three year relationship had just ended when she and Sara went out on their first date. The evening went hilariously sideways. Hear what happened next and whether time was on their side.

Olivia and Robert

ByJodi Klein

Olivia returns to the podcast to talk about a dating app match that was made in the US and led to a first date in Europe. Olivia and Robert texted regularly for three weeks before they met. She was sensing strong chemistry and a deep connection with him as their conversation progressed. Was Olivia right? Discover what happened when they had their debut date in London.

Laurie and Gary

ByJodi Klein

After ending her marriage of 26 years, Laurie had lost faith that she’d meet someone who has the qualities she’s looking for in a loving partner. Then she met Gary. Did they come into each other’s lives at the right time? Find out.

Leelah and Jack

ByJodi Klein

“Why am I not married yet?” is a question Leelah asked herself. She’d expected to be married long before she reached her late 40s. Leelah knew what she wanted and needed from a healthy loving relationship, but hadn’t found it with any of her ex-boyfriends. One night, not long after a breakup, she showed up at a potluck dinner with a rotisserie chicken. So did Jack. Was that a sign that they had something, in addition to a fondness for poultry, in common? Find out.

Siobhan and Carl

ByJodi Klein

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

ByJodi Klein

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.

Isabel and Zane

ByJodi Klein

It’s said that you need to know yourself before you can know who the right partner is for you. Isabel returns to the podcast to talk about how the unexpected happened when she focused on her own personal growth and embraced her vulnerabilities.

Lexi and Jerome

ByJodi Klein

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.