The Successful Woman’s Guide to Online Dating in Midlife

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online dating in midlife

My podcast guest, Dr. Joan Bragar, shares how she succeeded at online dating in midlife. Hear how she met her second husband and learn valuable tips!

My podcast guest, Dr. Joan Bragar, divorced when she was in her late fifties. She wanted to be in a committed relationship, so she learned how to date online successfully and found a loving husband. She shares this knowledge with her clients and readers of her book, Never Too Late for Love! The Successful Woman’s Guide to Online Dating in the Second Half of Life.

Joan is a certified Calling in “The One” and Conscious Uncoupling coach. Dr. Bragar has worked as a management consultant, a teacher of leadership and a coach to people around the world. She holds a doctorate from Harvard University and is the doting matriarch of a family of seven children and four grandchildren.

Check out highlights of EP 365: The Successful Woman’s Guide to Online Dating in the 2nd Half of Life

The Successful Woman’s Guide to Online Dating in Midlife

Listen to/download today’s episode below or by clicking here.

Can you share your story of online dating in midlife, and finding your husband?

I divorced at 57, and I knew I wanted to be in a relationship again. The first thing I did was reach out to Kathryn Woodward Thomas, the best coach I could find, to shift some limiting beliefs I had. One of my beliefs was I had to make it on my own.

I wasn’t going to meet that man at work, so my 30-year-old son got me started in online dating. I learned a lot from him. He said, “If a man likes you, he’ll let you know right away.” That was one of the biggest lessons. If a man doesn’t respond, that’s fine. You don’t want to learn anything about that!

What I found over two years and forty dates, was that half were attracted to me, and half of them weren’t. I learned that it’s fine. Don’t get upset, just move on. There was one man I dated for a few months, and I took him to California to meet my coach. She said he needs some development. I asked him if he’d ever go for help. He said, “No, I like myself the way I am”, and I ended that relationship.

I went out again. I kept asking myself, “Is this a good person?” I set the intention to find a man by age 60. Three months before my 60th birthday, a relationship fell apart. So, I went back online until I found my husband. I was unsure about him from his profile. We can’t tell a lot by a profile.

We spoke for five minutes on the phone. I was turned off by the short conversation, but we met at Starbucks anyway. I found out he had been online for eight years, and he knew he had to meet someone to find out if there’s a connection. He was a lovely warm-hearted man. I was struck by how different he was from the profile and phone call.

My must-haves were: in my geographic area, in my general age group, and educated. If they had all three, I would meet them.

We didn’t sleep together for the first three months. He wanted to be sure we’d be friends before getting into a relationship. And he was worth waiting for.

What are some of the key obstacles women face in online dating?

It’s not difficult to go on dates. It’s difficult to have your hopes up each time and become disappointed. It touches a deep wound in us, the younger part of ourselves. You have to upgrade parts of yourself so you can meet a man of value who will respect you. Let go of attachment to the outcome.

Obstacles for older women:

  • We’re afraid of online dating
  • We’re self-conscious about our looks at this age. (P.S. Many men are madly in love with women our age.)
  • We don’t want people telling us what to do. We want a man who’s respectful and empowering.

What are the most important things women need to learn to date online successfully?

Keep your focus on yourself when you’re dating. Notice how you’re feeling when you’re with a man. Do you feel comfortable, respected, relaxed, or do you feel uncomfortable and nervous?

Why is it so hard for strong, independent, successful women to succeed in finding love?

  1. I love working with successful women. The first thing is the myth that a man should earn more money than her. We don’t want to take care of and support a man. The man doesn’t have to be richer, but he does have to be self-sufficient.
  2. Redesign what you want from a partner. He doesn’t have to be your professional mentor, someone who’s going to challenge you professionally. You want someone who will be there for you no matter what and cares about your family as his own.
  3. We don’t want the 50s marriage where we’re a complete support system for a man. Design how you want your relationship to look. Find a man who doesn’t want a woman to support him at home. Negotiate what works for both of you.

For a free digital copy of Never Too Late for Love! The Successful Woman’s Guide to Online Dating in the Second Half of Life, write to All she asks in return is that you rate and review it on Amazon.

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Want to finally attract the epic love you deserve? Schedule your complimentary 1/2 hour Love Breakthrough Session. Learn how coaching with Sandy can help you fall in love with a partner who meets you on every level.


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