5 Women Share What It’s Really Like to Divorce and Date in Midlife

By Lauren Krouse
January 22, 2024

Dating at any age can be tough. But in the wake of a divorce, there’s often a lot of hang-ups, history, and trauma to untangle—all while navigating an entirely new dating pool.

If you’re feeling conflicted about what’s next, or have no idea how to date in the time of Hinge and eHarmony, know that you’re not alone. Since 1990, the divorce rate for people age 45 and older has increased, according to research by Bowling Green State University. For women ages 55 to 64, it’s nearly tripled. As you move forward, advice from others can help you find your bearings and start fresh.

With this in mind, we asked five women to get real about what divorce and dating is actually like in midlife. Here, they share the lessons they’ve learned so far, plus how they found happiness, with or without a new person.

1. Get to Know Yourself Better

Mary Joye, 65, Winter Haven, Florida

“I’ve been divorced twice in middle age. My first husband was extremely abusive. My second husband was even worse. After I left him, someone asked me if I didn’t trust men anymore, and I said no—I didn’t trust my ability to pick them. So, I went on a quest to change and get better.

“When you start dating again, I think it’s imperative that you understand anything you may be reenacting from your past that you may be bringing into your present relationships. In my case, this required counseling. I recommend seeing a therapist to help you listen to yourself.

“Working with a therapist and practicing meditation helped me stop being attracted to abusive people. In doing so, I found a very nice partner in life, and I’m more at peace now than ever before.”

2. Build Confidence Through Dating

Fiona Eckersley, 57, Milford, Connecticut

“When I started dating after divorce, I had to learn to stop listening to the voice in my head telling me I couldn’t do any better [in relationships] and to just put up with [bad behavior] so I wouldn’t be alone. In this crazy, mostly online dating world, it’s very easy to quickly become disillusioned when someone disappears or doesn’t communicate the way you’d like them to. But don’t take any of that personally.

“It’s better to go into this process with a sense of fun and adventure. For me, each relationship taught me so much about myself and what I wanted going forward. I like to say that it was like using a ‘boyfriend ladder,’ where each man was a rung that brought me closer to finding myself and what I wanted out of life.”

3. Know Your Boundaries

Jocelyn Hastie, 60, High River, Alberta, Canada

“After a divorce at 40, I started dating again and met a cowboy on an online dating site. As someone who worked with horses, I fell in love with the potential to build a true partnership in love and life.

“On our third date, he had a medical emergency, and I took him to the hospital. He told me he loved me—something I now understand was a warning sign—but I ignored it, thinking he was expressing gratitude.

“Over time, I continued to let things slide. I excused his interactions with single women on Facebook as part of his career in horse training. I excused lack of progress on his divorce because I assumed he was overwhelmed. And I excused his vicious comments about his wife as a result of the challenging situation he was in rather than a reflection of his character.

“When he finally crossed a line I couldn’t overlook or excuse, I threw in the towel. My main advice for other women is to draw clear and firm boundaries, trust your intuition, and avoid making excuses for bad behavior.”

4. Use the Opportunity to Create the Life You Want

Maria Leonard Olsen, 58, Bethesda, Maryland

“At 50, I got sober, divorced, became an empty nester, and was living alone for the first time in my life. I pretty much had to start my life over, and I felt rudderless.

“So, for my 50th birthday gift to myself, I decided to try 50 new things during my 50th year. This was a way to figure out how I wanted to live the next chapter of my life. Each new thing I tried taught me something about who I am and who I want to be.

“For instance, I moved to Nepal to volunteer at a school high in the Himalayas. The people there had very few material things—no running water or electricity—yet they were among the happiest and closest-knit communities I’ve ever encountered. Living with them, I came to value relationships much more than things.

“If you’re newly divorced, make a list of all the things you want to do and all the places you want to see before you die. Sort them by what you can do now and then get started. Surround yourself with people who bring out the best in you and have similar interests. And if you don't like your life, change it.”

5. Feel Free to Compare and Contrast

—Jodie Filogomo, 56, Sun City, Arizona

“After I got divorced around the age of 40, I teamed up with two of my single friends to start dating again. Together, we tried all sorts of ways to meet guys: speed dating, online dating, local events, the bars.

“The best tip I got was to date many guys at the same time before you become invested in them. This way, you know you have options and can move on more quickly if you see red flags with one of them.

“As I dated, I’d ask a couple of guys the same question to see how they’d react to different scenarios. For example, when I got a flat tire, I asked them what they’d do if I called them for help. One guy said he might have picked us up if he could get off work, another said that there was no way he could get away, while the man I would eventually marry said he would definitely have been there to get us home.

“I am not sure I would have even gotten serious with my husband back in my younger days, because I would have thought he was too nice. It took going through a terrible marriage and

divorce to realize that ‘nice’ is a good thing.”

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