Midlife Dating Adventures

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midlife dating

Midlife dating can be fun and adventurous. Listen to this episode with author and podcast host, Jodi Klein, to hear first date stories!

Jodi Klein is the author of “First Date Stories: Women’s Romantic and Ridiculous Midlife Adventures,” which was published September, 2021. She is the host of the podcast “First Date Stories” and blog of the same name. Jodi created the First Date Stories platform to help women navigate dating in midlife, share advice, and stay on course to find enduring love.

In EP 478 of the Last First Date Podcast:

  • Why Jodi wrote First Date Stories
  • Who was the Dame in Shining Armor?
  • How Jodi went on her last first date
  • 6 Dating Deterrents that can keep you single
  • What is a Seasoned Dater?

Midlife Dating Adventures

What motivated you to write First Date Stories?

I wrote it for two reasons. Because nobody has written a collection of first date stories in midlife. We need stories in our lives more than ever. The second reason was to help women in midlife feel like they’re in a midlife posse, and that they will be motivated to stay open to love. 

We get validation through our stories. I wanted to elevate women’s stories. I wanted to encourage women to keep showing up for first dates.

One of my favorite stories in your book is chapter 8, The Dame in Shining Armor. Can you share that story, and the great follow up?

This is a story about a woman named Julie who used to work with Steve. He left the company, and he asked her out to dinner a while later. And she was excited to see him as a possible romantic interest. She drives to PF Chang, and she sits at a table, orders a drink. He’s late. So, she orders food. She calls him, and he says he’s not coming. She’s upset, and calls her friend Samantha, who joins her at the restaurant.

Samantha comes into the restaurant, and acts like she’s the one Julie was waiting for. Julie makes a great experience out of being stood up. Listen to the full story on the podcast.

In the introduction of your book, you talk about Dating Deterrents. What are they?

There are challenges in midlife when you’re dating. I’ve identified six dating deterrents.

  1. Supply and demand. There are less single people, and it’s harder to find people to date. However, new people are constantly coming into the dating pool as their relationships end. They’re often better at dating.
  2. Life’s complications. As we age, we may have parents and children to take care of. We have mortgages to pay. 
  3. Societal pressures. Pressure to be coupled, and people find it hard to continue dating.
  4. Age. We live in an ageist society that celebrates youth. You may see someone your age looking for someone much younger.
  5. Fear of getting hurt again. You need to make yourself vulnerable in loving relationships, which requires risk. It’s the journey.
  6. Communal support. It’s important to have people in your life who will listen and share your journey. 

You’ve come up with the term “Seasoned Dater” to describe women who date longer than most people. Why did you feel it was necessary to come up with a new phrase and why that one?

I was in the dating scene for twenty six years after college. I know what it’s like to date much longer than you expect. I also know what it’s like to have people think there’s something wrong with you if you’re not married by a certain time. 

That expectation comes from an era of marriage as an economic partnership. We don’t need validation from being married anymore. We need to validate ourselves and celebrate who we are, as resilient women who believe in love. I wanted a term that conveyed dignity and expertise. Women love the term. 

Can you share your first date story, the last one in the book?

It was October 2014, and a friend had invited me to a party to watch the SF Giants. I wanted to go to the game, but I had already signed up for a networking event. I went to the event on my own, and because the game was going on, it was fairly empty, and people were paired up in twos and threes. One person was standing alone at the end of the room, and I decided to go stand with him. He walked to the food table, and I followed him. I started talking to him. He invited me to stand and eat with him. 

I wasn’t even thinking about him romantically, and while I was chewing, he asked me what my relationship status was. I almost choked. Find out what happened next in the podcast recording.

What’s your best advice for someone who wants to go on their last first date?

If you’re wondering where your person is, I’m living proof that you can meet at any age. We can also live a meaningful life as a single person. Believe and keep showing up. 

Watch this episode on YouTube


Jodie’s special offer: A Modern Day Dating Dictionary. You can find it on http://www.FirstDateStories.com. You can also find the podcast there. Find Jodi on Facebook @1stdates and Instagram @1st_datestories


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