Dating in Midlife: Insights and Wisdom Gained

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If you’re dating in midlife, you’ve probably experienced your share of heartbreak. These four ladies share what they learned about dating at this age.

I had so much fun interviewing the four “And I Thought Ladies”, discussing dating in midlife. These women have been interviewed on numerous shows for their unique approach to love. They bring four decades of life experiences to document their progress in understanding the keys to attracting in love, which begins in increasing self-love. These women span the gamut of relationships, from those who are survivors of abusive relationships, to those who are now happily married for several years. These four ladies empathize with women at any stage of love, because they have been there and have literally written two books about it!

Here’s the line up of the “And I Thought Ladies”: ​Wilnona is divorced after an emotionally abusive relationship. Jade, the youngest, found her Prince Charming after many years of dating, and she’s been married for four years. Dr. Argent has two doctorates and has dated around the world. She runs many businesses and is also an author. Renee had two divorces and now owns her own cleaning service with an awesome name, Divine Destiny.

Highlights of Episode 243: Four Perspectives on Love and Marriage in Midlife can be found below.


Dating in Midlife: Insights and Wisdom


​In your experience, what is the most difficult part of dating in midlife, and how did you overcome it?


Jade: Inflexibility. Being flexible was so important in trying to find the man of my dreams. I learned to accept someone as they are, not as you want him to be.

Wilnona: The hardest part of starting a new relationship was learning to trust again. It’s hard to let someone in. I overcame it by taking time to discover what went wrong in past relationships. And I started developing friendships with men before diving into a relationship as I began dating in midlife.

Renee: I had a hard time building trust again, too. You’ve gone through so much deception, and to be able to let someone into your heart again is difficult. Once you stop only looking for faults in a potential partner, you can more easily find the ‘one’. Also, when you get to the point where you can love yourself first, that also makes it easier. You’re thinking less of what he thinks of you.

Dr. Argent: I felt I compromised too much in the past, and it wasn’t reciprocated. Women have been conditioned that it’s our job to compromise and do for others.

When dating in midlife, how can you create a healthier relationship, especially when you’ve always been a giver?


Jade: Set boundaries and ask for what you want. My husband does the vacuuming, because we both work all day. I set a clear boundary about what I needed, and we both contribute to keeping the house clean.

Wilnona: I’m a super giver, until my heart breaks. I’m now setting boundaries with the help of Jade and Dr. Argent.

Renee: When I first got married, my mom said to me, however you start out in a relationship, that’s what he’ll expect from you throughout. I found that to be true in my marriage. When I first got married, I cooked, cleaned, and played the role of a wife. When I was tired and pregnant, everything still fell on my shoulders. I was unhappy. Then I went back to what my mom said. Because I hadn’t set clear standards from the beginning, it became a big misunderstanding in the relationship. Had we communicated at the start of the relationship, we could have made it work and compromise together. Instead, we grew apart.

Dr. Argent: Know yourself first. Then communicate your wants and needs and desires. Make the time to do that. Don’t rush into the relationship. Take the time to talk and listen. It’s not just using your ears, it’s paying attention to the little details. Watch the body language as well as the words. That will get you out of a lot of bad relationships. Use dating as a tool to weed out undesirable situations. And don’t forget to have fun.





Listen to the entire episode here.

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