Stories of Divorced Women Dating in Midlife

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.

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.

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.

Juliana and Dan

ByJodi Klein

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.

Ruth and Mark

ByJodi Klein

Blind dates can be a good way to meet men. Sometimes people make presumptions about who they’re going out with based on what they know about the person who made the introduction. When a friend set Ruth up with Mark, she made a lot of assumptions about him that turned out to be very wrong.

Jamie and Barb

ByJodi Klein

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.

Monica and Rich

ByJodi Klein

What’s it like to date after a bitter divorce? In our Season 2 finale, Monica returns to talk about the atypical way she got started with online dating, how she got her groove back, and her first date with a man who she asked out.

Tara and Lee

ByJodi Klein

Tara’s husband was an alcoholic. Their marriage fell apart. She started dating online to help her heal from the devastating divorce. Tara wanted to find a fun companion, not another husband. Hear how she met Lee and about their spontaneous first date.

Tabatha and Richard

ByJodi Klein

Sometimes people turn out to be very different than they seemed on a first date. That’s what Tabatha discovered after a well-intentioned friend set her up with Richard. The date went great. What happened afterwards wasn’t.

Monica and Scott

ByJodi Klein

Monica was devastated when her physician husband of 21 years left her for his nurse. A bitter divorce followed. A friend eventually convinced her to start dating again. Monica shares how she found bravery within and went on a memorable first post-divorce date with Scott.