New Book Contains Hilarious Stories Of Women Trying to Navigate First Dates in Midlife

The following is an excerpt from Jodi Klein’s upcoming book ‘First Date Stories’ (She Writes Press, September 14), where readers experience the ups and downs of love with the powerful reminder that being single is something to be celebrated. It is a collection of true tales, combined with takeaway tips and meaningful quotes. Before a promising first date, or after an awful one, ‘First Date Stories’ helps build dating confidence and reminds readers that others have been where they are, and that every initial encounter could turn into something long-lasting and wonderful.

“How about we get something to eat?” Brad asked as we left the independent bookstore where he’d suggested we meet.  

“Sounds good to me,” I responded, smiling. I was pleased that he looked like his photos and that his personal specs—height and eye color—were as advertised. I’d been on too many dates where the man who showed up wasn’t true to the guy I previewed online. Brad didn’t disappoint.  

We strolled down Santa Cruz Avenue, chatting under the early afternoon sun. The conversation flowed nicely. We hit many of the first date standards: hometowns, jobs, weather, sports. I easily kept up with his gait and sensed a slight bounce in my step. It didn’t matter that I had no idea where we’d be eating. I’d let my handsome six-foot companion surprise me. 

As we approached the local grocery store, Brad veered off the sidewalk. I followed him across the parking lot and into the store, all the while wondering what he could possibly need to pick up. Was he running an errand on our date?  

Brad headed directly to the deli counter. I watched him as he leaned down and surveyed the cornucopia of salads and other prepared food on display in the glass cooling case. He stood up and waved over one of the deli assistants. When she approached, he rested his pointer finger against the glass to direct her attention to the mound of premade food in front of him. I stood speechless, my eyes transfixed on Brad’s every move. 

“Can I taste the corn and chicken salad?” he asked. The clerk handed him a small fork and one bite of salad in a plastic ramekin. He turned to me. “What are you going to taste?” 

“Uhhh . . .” I glanced into the case. “I’ll try the lentil salad,” I replied cautiously.   

“She’ll have the lentil salad,” Brad repeated to the grocery employee, in the familiar manner a man uses when he’s ordering for his companion at a restaurant.  

The plastic cup with its spoonful of salad remained untouched in my hand as I watched Brad taste his way through most of the items in the display case. I was baffled. Then it hit me: He’s taken me to the grocery store’s deli counter to sample food for free for our first date! 


Oh, Brad! This “romantic” deli counter outing was one of the more memorable first dates I’ve been on. I’m a seasoned dater— an alumna of nearly four hundred dates. Dating for decades isn’t something that people usually tout. But why not? Isn’t it better to wait to meet the right partner than to divorce the wrong one? Many women who reach their thirty-fifth birthday single, or rejoin the dating scene later in life, know that finding enduring love can be tough. The hardest part isn’t finding men to go out with. Thanks to that multitalented phone that’s probably within arm’s reach of you right now, you’re likely just one dating app and a series of swipes or thumb taps away from getting a flirtatious conversation going with some guy, somewhere.  

But it is incredibly hard to find a man with whom you want to develop a fulfilling relationship—and it’s even more difficult to find a man with whom you want to build a life. I should know. I became a master at going on first dates. 

The first date is where every relationship begins. The first date is all about detecting a spark, even just a hint of a connection. You may think you’ve sensed that spark from texts, e-mails, or calls between you and the man who’s caught your eye, or from a virtual date that the two of you have had. But you can’t be sure. It’s only when you’re with him in person that you can accurately detect whether or not there’s chemistry. All your senses are activated, taking in his presence, level of energy, appearance, body language, and even his personal scent. Your mind is consciously, and subconsciously, in assessment mode.  

Do I feel safe with him?  

Does he seem nice?  

How well does our conversation flow?  

Do we have things in common?  

Am I attracted to him—his personality, his looks?  

Does he make me laugh? 

Could I see myself kissing him?  

Do I want to spend more time with him? 

You get the idea. There are a series of questions that people answer for themselves during and after each date. And there are plenty of additional questions that we have to find the answers to for that first “hello” to evolve into a committed relationship. 

I was—and remain—a big believer in the power and necessity of hope. The hope that my next first date would trigger that sought-after spark was one of two things that kept me in the dating world for twenty-six years after college. The other is my deep-seated belief that every woman who wants to be coupled is worthy and deserving of enjoying a lifelong, loving relationship with her ideal match.

Jodi Klein is the author of First Date Stories: Women’s Romantic and Ridiculous Midlife Adventures, which will be published in September 2021 by She Writes Press. A demanding career and desire to find the right “Mr. Yes” for her led to Jodi becoming an alumna of nearly 400 dates over the course of 26 years. She founded First Date Stories—the podcast and the blog—as a platform for women to share their tales and wisdom so that others can overcome the trials of dating in midlife and find the long-term love they seek. Jodi is a graduate of UC Davis and holds an MBA from the Ross School of Business at the University of Michigan. She lives with her husband in San Francisco, where she spends time working with non-profits on social causes and rooting for her favorite sports teams.