The Scoop: Many adult women are actively dating and hoping to meet a long-term partner. Their first date experiences are a mixed bag of good, bad, ugly, awkward, and everything in between. Inspired by her own dating experiences, author Jody Klein decided to investigate the nuances of first dates by talking to singles on the ground. She began interviewing women for her podcast and blog First Date Stories, and the idea took on a life of its own. Now Jodi is about to publish a book that will give readers a good laugh and make them feel a little more hopeful about their next first date.

Jodi Klein talks a lot about first dates and chance encounters in her soon-to-be published book, “First Date Stories: Women’s Romantic and Ridiculous Midlife Adventures.” She has collected many stories from friends and colleagues, but her favorite first date story comes from her own love life.

At the time, Jodi wasn’t even certain her first date with the man she would later marry was a first date. She and her future husband had met at a networking event, and he had contacted her the next day on LinkedIn, so it could very well have been a business meeting rather than a coffee date.

“Given that he’d messaged me on a business platform, I wasn’t sure if we’d scheduled a networking or personal rendezvous,” Jodi said with a laugh. 

Photo of Jodi Klein
Jodi Klein created a podcast to share fun first date stories from real women.

The couple had agreed to meet at a coffee shop on a Friday afternoon, but Jodi had gotten stuck in a heinously bad traffic jam on the narrow streets of San Francisco.

“Only then did I discover that downtown streets had been unexpectedly shut because the president of the United States was at a meeting! Multiple times I considered canceling and turning around,” she told us. 

Fortunately, Jodi decided to press on and arrived at the café 45 minutes late. She now says that it was well worth the wait. She and her date clicked instantly, and they didn’t talk about business at all.

“I was attracted to him and comfortable in his company. It all felt easy. Natural. When we said our goodbyes, he commented that we should get together again,” she said. 

Jodi got engaged 10 months later. Not long after, she happily said “I do” and tied the knot for the first time at the age of 49.

After many unsuccessful first dates, Jodi met her perfect match, and now she wants to give hope to other single women in their 30s, 40s, and older. She wrote “First Date Stories” to talk about the important first building block to a relationship and show that it only has to work once to be a happily-ever-after story.

Showing Women They Don’t Have to Settle as They Age 

Jodi went on over 400 first dates in her search for love, and she was determined not to settle for a man who didn’t live up to her expectations. Over the course of 26 years, she accumulated many good, bad, and middling date stories before she met her Mr. Right.

"First Date Stories" cover
Now the “First Date Stories” book has new tales to tell about love and romance.

While dating in her 30s and 40s, Jodi realized how easy it is to feel isolated as her friends settled into married life and had children.

“By the time I reached midlife, dating had gone from being a supportive, shared adventure to what often felt like a solo journey,” Jodi said.

Jodi connected with single women over 35 and decided to give her all to this community by telling her story — and then telling her friends’ stories, and then telling more stories that put dating in perspective. That’s how “First Date Stories” came to be.

The ultimate goal of sharing these experiences is to let older single women know they’re not the only ones going through difficulties or feeling frustrated.

“Many of the women I met were giving up on finding the love that they desired,” she told us. 

Jodi hit her stride when she began writing her real-life experiences with first dates in a short story writing group. Group members always asked what happened after the dates, so she created a section called “The Rest of the Story.” This section helped Jodi put what she had learned into words and recognize the value in each first date. 

“What started out as a side project evolved into this book. While the publishing process takes a long time, creating a podcast doesn’t. My heightened desire to elevate women’s stories led me to launch the podcast and the blog in tandem while I continued to work on the book,” Jodi said. 

The Book Offers Supportive and Eye-Opening Date Stories 

Jodi has focused on the idea of first dates in her podcast, blog, and book because she sees a lot to learn from these experiences. She tells singles that all first dates can be opportunities to learn and grow. Her book includes plenty of dating advice as well as quotes from real single women who have shared their stories.

“First Date Stories” includes a mix of good and bad experiences, but its overall message is a positive one. Jodi emphasizes that every first date holds the possibility of a significant connection, and it’s important to never give up hope.

A story called “The Day Trip” focuses on Mark and Jennifer, who had been friends since childhood. They knew each other well and had never been romantically interested. Until one day that changed everything. Standing at the top of a ski slope, Mark said he was looking at a “gorgeous view.” 

“She thought he meant the vistas surrounding them. He meant her. At that moment, she began to see him in a whole new light,” said Jodi. 

Women can gain perspective by hearing about other people’s experiences.

Of course, not all first dates end happily. Some end with a grimace. “The Cringe” tells the story of the first date between Adam and Maria. During their encounter, Adam insisted he was not an insensitive man, exclaiming, “I’m not some guy who is all jacked up on testosterone. I have a soft side. For goodness sake, I like cats!”

Jodi weaves together stories that make readers laugh and make them think. It’s a fun jaunt into the modern dating scene as told by a woman who has been in her readers’ shoes.

The early reviews for “First Date Stories” have been overwhelmingly positive. One reader wrote that she “loved reading all the stories and advice given” and that the book “makes you realize again that not everyone is for you, but you have to keep putting yourself out there.”  

Another said, “This book is sure to be of benefit to anyone who is hesitant to put themselves out there in the search for human connection and love.” 

In addition to reading the book, single women can check out the fourth season of the podcast or the dating insights blog for advice and encouragement from experts who are intimately acquainted with the first date and beyond. 

First Date Stories Help Single Women Understand Themselves

Many single women have found comfort and connection within the pages of “First Date Stories.” Some readers relate to the newly divorced or widowed singles who haven’t been on a date in years or decades. They learn to overcome their fears by hearing positive stories and knowing what to expect.

“First Date Stories” is at its heart an optimistic book about everything that could go right on a first date. While some stories can be awkward or cringy, the takeaway is that singles need to be resilient and keep accepting opportunities to meet people. After all, the more first dates a woman has, the more likely she is to find a compatible partner.

“The tone of the book is hopeful. I want all daters to believe that they can find love, no matter how unlikely it may seem at times. To do that, they must keep going on first dates,” Jodi said. “Dating is a numbers game. The more people you meet, the greater chance you have to encounter your ‘Mr. Yes’ or ‘Ms. Yes.'” 

Instead of being discouraged by a bad first date, the women in Jodi’s book show character by getting back out there and recommitting themselves to the idea of love. Jodi highlights these stories to show single women that they aren’t alone. The First Date Stories blog, podcast, and book have created a community around authentic, love-driven people.

“Millions of women in midlife are riding the first date-rollercoaster. ‘First Date Stories’ will help them take the ride together,” Jodi said. 

Advertiser Disclosure is a free online resource that offers valuable content and comparison services to users. To keep this resource 100% free, we receive compensation from many of the offers listed on the site. Along with key review factors, this compensation may impact how and where products appear on the page (including, for example, the order in which they appear). does not include the entire universe of available offers. Editorial opinions expressed on the site are strictly our own and are not provided, endorsed, or approved by advertisers. Our Editorial Review Policy Our site is committed to publishing independent, accurate content guided by strict editorial guidelines. Before articles and reviews are published on our site, they undergo a thorough review process performed by a team of independent editors and subject-matter experts to ensure the content’s accuracy, timeliness, and impartiality. Our editorial team is separate and independent of our site’s advertisers, and the opinions they express on our site are their own. To read more about our team members and their editorial backgrounds, please visit our site’s About page.