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Jodi Klein: Supporting All the Midlife Single Ladies

Moving on from her career in marketing, she’s determined to help those out in the dating trenches. Tiffany Connolly finds out how a new business was born.

Jodi Klein comes across right away as someone who could easily be your best friend. She is warm and open and loves the camaraderie that comes from a network of supporting girlfriends. After spending years working in marketing for high-tech firms, Klein, 52, ventured out on her own to launch a platform of support and connection for single women who are dating, or considering dating later in life. She built First Date Stories from the ground up after coming to the realization that there was very little, if anything at all, available to encourage women in midlife and beyond who are navigating the modern dating scene. First Date Stories is a website and podcast structured to offer dating advice, encouragement, and the best part—true first date stories from women who are dating later in life. I caught up with her one late afternoon for a chat.

Where did the inspiration for First Date Stories come from?

I spent 26 years in the dating scene after college. And for most of my 30s, I put my career in high-tech marketing before all else. As the years passed and many of my single friends became coupled and started building families, I realized that there was very little available to support and connect single women in midlife. That made no sense to me. Where were the other women to share dating stories? The joyful, the ridiculous, and the downright horrible kind? Where was the support and encouragement to remain or re-enter the dating world? Women are fueled by community and connection. I knew there were millions of women in this place in life, and I thought that something needed to exist to improve things for them, or at least help them along. Since no one else had done it, I decided that I would.

Read More: The Types of Men You’ll Meet While Online Dating After 50

Did you find a man yourself? Would you consider yourself a successful dater?

Yes! I finally met an amazing man. I knew soon after we started dating that he was the person I wanted to be with for the rest of my life. We went on our first date when I was 47 years old, and we married when I was 49. He was absolutely worth the wait!

Where were the other women to share dating stories? The joyful, the ridiculous, and the downright horrible?

I was a very successful dater, not because I found my life partner, but because I enjoyed meeting (most) of the men I went out with, and I became very good at talking to almost anyone about almost anything. I also had fun getting to know the men with whom I felt a connection. I grew as a person because of it—and this includes the many disappointments that I experienced along the way. Being a successful dater also means not settling for the wrong partner just for the sake of being in a relationship. I decided that I’d rather live a wonderful, fulfilling, and independent existence rather than be with a man who I knew in my gut was not the right long-term partner for me.

You worked in marketing for years. What was involved in making the switch from working for others to working for yourself?

It was quite emotional at first. I needed to revisit my personal dating journeys and examine what I could have done differently and what worked well. I had to take a deeper look within. And I knew I would need to share my own tales with the public. To do all this I had to become comfortable with being vulnerable. I’m not entirely there yet, but I am making progress, and I feel like I’m growing as a person as a result.

As a business owner I had to learn how to rely entirely on myself. I had to make sure I was 100 percent committed. When you start a business, you are the driver and the mechanic. You have to acquire all the parts, put them together, and then take the driver’s seat. But I realized soon that I couldn’t do it all myself. It was really important for me to find a team who really believed in the mission just as much as I did.

First Date Stories premiered in December 2018. What are some successes you have had so far and what do you attribute them to?

Even though the business is less than six months old, we’re already starting to hear that the stories and advice articles that we’re sharing are having the positive impact we’d hoped they would. The other day I heard that a woman in her early 60s listened to all the available episodes on the days leading up to a first date she was going on. Listening helped boost her confidence to rock it while on the date, and it made her more excited to go!

Being a successful dater also means not settling for the wrong partner just for the sake of being in a relationship.

I’m also thrilled that we’re successfully sparking sisterhood. When I speak with women about being guests on the podcast and explain that telling their first date story is a way to help other women be more in the know about dating and possibly feel less alone on their journeys, these women almost universally want to participate. Although the guests will likely never meet the listeners, they are moved by the desire to help other women. I’ve loved that!

First Date Stories: A Network Helping Midlife Ladies in the Dating Trenches | NextTribe

Wise words from First Date Stories. Image: First Date Stories/Facebook

What’s one of the best First Date Stories you’ve been told on the podcast?  

All the women who have been guests on the podcast have had wonderful and memorable stories to share. One of the most unique stories was told by Elizabeth, a woman who was in her 40s and felt her biological clock ticking.  She wanted to be a mom, but she didn’t have a man in her life. So, Elizabeth decided to go it alone. With the help of a sperm bank, she got pregnant and was on her way to becoming a single mother. Then Tom, a childhood crush who had gotten away, asked her to dinner. I hate to give away the rest of what happened during their first date and beyond—I’d really rather let Elizabeth do it! She tells it so beautifully in the episode aptly titled “Elizabeth and Tom.” It’s a story that should be heard by every woman who’s in a similar place in life today as Elizabeth was then.

Read More: Divorced at Midlife… Now What? Tales From the Trenches of Online Dating (and Some Advice)

What skills and experience from your previous career have been useful?

As a marketer, I worked for and with companies, helping them build and launch brands, gain awareness with customers, generate leads and conversions, and secure customer loyalty. All of those skills are transferable to First Date Stories. However, much of my experience involved marketing to business customers, and I’ve never worked in the field of psychology before. So I’m adapting and building on what I know for the wonderful female audience we are seeking to reach and positively impact.

If you don’t show up for a first date, there will never be a second that could lead to a tenth and beyond.

What new skills have you developed through this endeavor?

I knew absolutely nothing about producing or hosting podcasts, even though I’m a huge fan of them! I’d never been involved in creating any sort of media program. The podcast concept tested well during the focus group interviews I held, so I knew I had to do it. But, up to that point, the only interviewing I’d ever done was to hire new employees. I had to learn it all from scratch. I read a lot about starting and growing a podcast, and I talked to a few people who had podcasts of their own. I learned how to interview people for my podcasts and how to use my voice in broadcasting and in a way I have never used it before.

What is your biggest hope for the women you are reaching?

For those women who want to be in a loving long-term relationship, my hope is that they stay active in their communities and have new experiences that introduce them to new people, overcome any emotional barriers that may be in their way, and believe and commit to the dating process with all its ups and downs, so they can meet the right loving partner. If they don’t show up for a first date, there will never be a second that could lead to a tenth and eventually the possibility of enduring life-long love.

By Tiffany Connolly


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