top of page
  • Writer's pictureGuest

Hilarious Midlife Dating Stories | Author Interview

Q+A with Jodi Klein, Author & Podcast Host of First Date Stories

1) What's your book about?

First dates can be triumphant, disastrous and the source of unforgettable tales. The book First Date Stories: Women’s Romantic and Ridiculous Midlife Adventures is a collection of entertaining, heartwarming and horrific debut encounters that also provide a roadmap to navigating the modern dating scene later-in-life.

I know very well what it’s like to date in midlife and how different it is from dating in your 20s. It can be wonderful, frustrating, exciting, baffling, isolating and so many other things. I wrote this book to help never married, divorced and widowed women feel like they’re part of a midlife posse and to encourage readers to keep going on first dates if they want to find enduring love.

2) When you first launched your podcast, was it hard to find guests who were open to sharing their dating tales?

After I came up with the idea for the podcast “First Date Stories,” I started to discuss it with uncoupled women in their 30s – 60s to get their thoughts and opinions about the concept. They told me that they were eager to hear what other women in midlife were experiencing in the dating scene since they often didn’t know many, or even any, other women who were dating.

When I asked them whether they’d feel comfortable coming on the show to share one of their incredible dating stories the answer was often “yes,” but only if I didn’t use their real name. So that’s why the majority of the guests who I interview are using a different name of their choosing.

Implementing the “anonymous policy” made it a lot easier to attract guests. And it’s also made the women who I’ve interviewed feel comfortable speaking candidly and sharing openly.

3) Do you have a funny or memorable first date story?

I sure do! How can I not after dating for 26 years? One of the most bizarre and

memorable first dates I went on is told in the tale that opens the book.

Brad and I had met on Match and made plans to rendezvous at a local bookstore. 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.

He suggested we get something to eat. As we strolled down the avenue, chatting under the early afternoon sun, 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?

Photo Credit: Flickr @chotda

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 pre-made food in front of him. I stood speechless, my eyes transfixed on Brad’s every move.

He asked to taste the corn salad and the chicken salad. Then he turned to me and asked me what I wanted. It was only after I cautiously replied that I’d try the lentil salad that I realized… he’d taken me to the grocery store’s deli counter to sample food for free for our first date!

“...he’d taken me to the grocery store’s deli counter to sample food for free for our first date!”

4)  What sort of level of expectations do you think people should have on a first date? For example: If you set your expectations low, everything is a wonderful surprise. Do you agree?

Yes, I completely agree. I strongly recommend that when you go on a date, you show up thinking that your time will be well spent if you’re able to have an enjoyable conversation with the person and learn one new thing you didn’t know before. Just one thing. That’s it. Look at every first date as a chance to enhance your life. Maybe you learn about a new movie, a new restaurant or a new place to travel to. After I adopted this approach, my first date stress evaporated.

“It’s natural to be nervous when you’re with a stranger...”

No one should show up to a first date with the expectation that they’re going to meet their life partner. If you do that, you’ve set the bar so incredibly high that you’re likely to be disappointed.

People often are not at their best the first time they meet someone new. It’s natural to be nervous when you’re with a stranger, especially someone who you’re intrigued by or excited about getting to know. Unless there’s a very obvious issue that turns you off about the person, dial the judgement meter way down. Otherwise, you could unintentionally take a promising meeting and sabotage it.

5)  Do you think it's harder for people in midlife (40+, 50+, etc) to date or find something long-term, versus someone in their 20's?

This question is a tough one to answer definitively. Yes, it can be harder to date in midlife, but there’s also a lot about dating later-in-life that’s better than dating in your twenties and early thirties.

When you’re in midlife you have already or are closer to accepting and embracing the true you with all your splendor and imperfections. You’re probably more confident than you were in your twenties. You’re more emotionally mature with years spent accumulating perspective and wisdom. You know what you’ll welcome and what you won’t stand for. You take things less personally. You show up for a date as who you truly are and not as who you think the person you’re meeting expects you to be. You’re more likely to take risks and go out with people who are not your type, opening you up to new possibilities. All these factors and many others can make dating in midlife a lot more fun, fruitful and life-affirming.

Author and Podcast Host Jodi Klein championing Midlife Empowerment .  Dating advice for women over 40, over 50, and over 60
Book Launch with Author Jodi Klein

If you’re interested in getting out and meeting people, it’s often easier to find a person to go on a date with thanks to that multitalented phone that most of us carry with us almost everywhere we go. It only takes one dating app and a series of swipes or thumb taps to get a flirtatious conversation going with someone, somewhere.

But it’s true that the dating pool shrinks as we age. The classic law of supply and demand can make it more difficult to find that special standout person with whom you want to develop a fulfilling relationship and life.

The good news is that many of the people coming out of marriages and long-term relationships return to the dating scene more mature and self-aware than they were earlier in life. Their re-entry raises the caliber of people who are available to meet. At the same time, as we get older it becomes harder for many of us to date at the same pace as we did in our twenties. Let’s face it. Our days get jam-packed with all sorts of obligations, commitments, and complexities related to our job, family, finances, health and other day-to-day matters.

What dating in midlife can also lack is the communal support and comradery that comes from having a group of friends who are in the dating scene with you. Some people have that support system. Those who don’t have wing-women or wing-men or people to swap stories with can find the Dating App Era to be especially baffling and frustrating. One of the reasons that I wrote the book and started the podcast was to help fill the void that the absence of a midlife posse can create for women.

“Look at every first date as a chance to enhance your life.”

AMAZON LINK (Links to Book): "First Date Stories" by Jodi Klein First Date Stories is a collection of tales never before heard on the podcast. Along with dating tips and inspirational quotes.


Jodi Klein, Author & Podcast Host

Jodi Klein is the author of the award-winning book, First Date Stories: Women’s Romantic and Ridiculous Midlife Adventures and the host of the podcast First Date Stories. Her writings have appeared on Covey Club, Brit + Co, Jumble & Flow, Revel

and Residence 11. Jodi is an entrepreneur, a marketing executive, a real estate broker, and the president of Espoir Ventures, LLC. She is a graduate of UC Davis and holds an MBA from the Ross School of Business at the University of Michigan. Jodi lives in San Francisco with her husband.

Editorial images are photo courtesy of Jodi Klein.


Editorial images are photo courtesy of Jodi Klein. Contributors Disclaimer: Submissions are memoir. It reflects the authors/guests present recollections of experiences over time. Some names and characteristics have been changed, some events have been compressed, and some dialogue has been recreated. Personal stories are not intended to hurt others-- the intention of this blog is to inspire and entertain.

bottom of page