An image of a woman in some fun pajamas looking at a dating app showing what it is like for women dating in their 40s.

Dating in Your 40s: A Journey of Strength and Self-Love

Dating in Your 40s: Written by Prudence Lybeck

Dating in your 40s, being resilient, and being an independent woman looks like me. It’s about embracing my journey, finding strength in my independence, and facing life’s ups and downs with unwavering determination.

I’m charting my own path, pursuing my passions, and defining success on my terms. It’s not always easy, but I’m resilient and know I can handle whatever comes my way.

My journey has consisted of grief, humor, confusion, resilience, inner strength, dating sites, and several repeats of the ever-awkward “first date.” Over time, my approach to dating has evolved.

I’ve learned to navigate societal norms and expectations, especially as a woman over 40, and to embrace the wisdom and self-awareness that come with age.

A photo of the author from her 40th birthday photo shoot.

The Stages of Grief and Finding Resilience

After I left my husband, I cried for three months. No one expects to get divorced when they enter a marriage, and I was no different. In the beginning, denial was strong.

I thought a few more days of crying would make everything better. I believed he would see the need to change. At the time, I didn’t realize then how much I contributed to our issues, but I now know better.

I was angry at the world. Every happy couple I saw seemed to mock me. Even my pets, wanting affection, felt like they were too needy.

I started dating too quickly, clinging to anyone who might fill the void. I even made a few videos about this. Then, I started bargaining with myself, thinking everything would return to normal if I were good enough for the next person.

Depression was the scariest part of my grief. It hit me hard, and I circled back to it often. I was adamant with my therapist and doctor about managing my medication.

I knew I couldn’t fall into a deep depression again. After all, I had two children who relied on me. I thought I had found acceptance by doing all the stereotypical post-divorce activities. I walked, drank water, taped affirmations to my mirror, and even went to yoga in the park.

But I still couldn’t find that elusive self-love everyone talked about. Why wasn’t it working? Little did I realize I already had the foundation. I just needed confidence.

Embracing Independence and Strength While Looking For Romance

At 40, I’ve come to understand the true meaning of resilience. As a single mother for the past six years, raising my 13-year-old son and 12-year-old daughter has been both a joy and a challenge.

I’ve dedicated 17 years to my career as a special education teacher and am about to complete my second master’s degree in education in July 2024. Soon, I’ll be one of only a handful of teachers in Montana qualified to teach students with visual impairments. 

Navigating the dating world has been a rollercoaster. Despite the difficulties, I haven’t given up. Five years into my single life, I was told to write a book, but instead, I turned to TikTok.

A quote from the author about dating in your 40s against the backdrop of one of her birthday shoot photos.

What started as a joke, sharing my crazy dating stories quickly grew into a community where people offered me valuable advice.

The Adventures and Misadventures of the First Date After Divorce

Some of my dating experiences have been outrageous. Some of these dates were with people I met online. One date spent the entire evening smelling my hair.

I’ve had dates where I felt like a teacher, lecturing the whole time, and one where the guy showed up without a wallet. I even went on a blind date with a good friend’s ex-husband, unknowingly.

It was an enlightening experience—I totally understood why she left him. Another brought a cheap sex toy attached to a cord and asked me to put it in my panties. I was so taken aback that I didn’t know how to respond. I finished my drink, excused myself, and politely left.

People have given solid advice, including the suggestion to volunteer more. This made me laugh because, during the school year alone, I volunteered 155 hours, not counting my involvement in my kids’ sports and activities.

Building a Supportive Community

This past year, I’ve focused heavily on self-help and healing. I even started a business with another teacher, producing ethically sourced wool dreadlock extensions from sheep raised right here in Billings, Montana.

Through self-help books, continuing education, and relearning boundaries, I’ve made significant strides in my personal growth.

I’m a strong, independent woman who pays all her bills and doesn’t need to rely on anyone else. While my confidence and success might be intimidating to some men, I remain unapologetically confident.


Mental Health and Personal Safety

Mental health is a lifelong journey of discovering our true selves and is the foundation of building resilience. It’s a crucial part of my path and deeply important to me. As a suicide survivor, with my first attempt at 13 and my last at 34, I’ve come a long way.

Today, I’m in a great mental place with a wonderful support system, surrounded by amazing women who uplift and encourage each other.

During my second year of being single, I was a bit naive and had a terrifying experience with a man who didn’t respect my boundaries. Despite saying no, he did not care, leaving me bruised and scared.

Rather than let this experience defeat me, I decided to work with other single women online and my close single friends on ways to be safer.

We share our GPS locations, give each other our names and addresses, and always answer texts and calls during dates. If I don’t respond, my bestie knows to show up. Women have to support women.

Discovering Self-Help and Setting Boundaries

Finding resilience wasn’t an easy path, but it was a deeply personal one. First, I had to figure out what truly worked for me, not just follow everyone else’s advice. While I appreciated the suggestions at first, I realized I needed to make sense of my own feelings and experiences to identify my own issues.

I knew my love language, but discovering I was an anxious-avoidant in relationships was a game-changer. This insight helped me look inward and understand what I needed to build my resilience.

I started reading self-help books with a fresh perspective, genuinely considering their advice. Conversations with my therapist became more open and actionable, helping me become a better person.

Teal Swan’s “How to Love Yourself” was particularly transformative, changing my views on self-love and healing.

I surrounded myself with like-minded women—successful, hardworking mothers who had also gone through divorce and emerged stronger. These women, who support and uplift each other, became my tribe.

A quote from the author about dating in your 40s set against the backdrop of one of her birthday photos.

Navigating social media, I chose to follow positive creators who helped me find my inner strength through their healing journeys. Some even encouraged me to share my own dating stories, adding a touch of humor and connection to my process.

Setting boundaries was one of the hardest yet most crucial steps. I established clear limits for myself and my dating life, recognizing that everyone’s boundaries and desires are unique.

Inspired by Hope With Holly on TikTok, who set clear expectations for her dating life, I created my own “Practical Magic” spell and made a solid list of what I wanted in a relationship.

Expectations and Moving Forward in My Quest for True Love

Regarding my approach to dating, I clearly understand what I’m looking for in a partner and what I expect from myself. Here’s my list, written in a style that reflects my journey and expectations:

  1. Embrace Humanity: Above all, be a beacon of kindness and compassion.

  2. Cart Courtesy: Small gestures matter—like returning shopping carts.

  3. Belief System: Whether it’s star stuff or Mother Earth, have a belief that fuels your soul.

  4. Respectful Differences: Embrace the beauty of diversity, especially in beliefs.

  5. Individuality: Flourish independently, even within the warmth of our bond.

  6. Shape and Color: Show me your essence through your favorite shape and color—it’s like a glimpse into your soul.

  7. Smile Often: Let your smile light up not just your face but our world.

  8. Intellectual Banter: Engage me in conversations that span galaxies of topics.

  9. Graceful Debates: Disagree with grace, for in differences lies growth.

  10. Handy Skills: Be a wizard at fixing life’s little glitches, or at least be willing to try to problem-solve.

I Am Very Thorough About These…

  1. Dynamic Partnership: Acknowledge that balance is fluid, and sometimes, it’s okay if it tilts. Relationships aren’t always 50/50; some days, they’re 20/80 or 40/60.

  2. Household Harmony: Let’s share the load, making our home a sanctuary for both.

  3. Parenting Respect: Honor each other’s parenting journey with understanding.

  4. Reciprocal Initiative: Show me you’re equally invested in words and actions. Communicate reliably and consistently without needing to be chased.

  5. Passionate Connection: Seek not just my body but the depths of my soul. Maintain a strong and active sexual connection, including mutual affection.

  6. Self-Assured: Be secure in yourself; knowing my quirks only adds to my charm. Understand that I need my independence, even though I’m scatterbrained (also, I’m super tall for a woman).

  7. Foundations First: Understand that intimacy blooms from a foundation of trust and connection. Focus on building a relationship before jumping into physical intimacy.

  8. Public Affection: Hold my hand, and if the moment calls for it, a playful squeeze is always welcome.

  9. Age Harmony: Let’s navigate life’s chapters with a shared perspective, no more than five years younger.

  10. Financial Independence: Stand tall in your self-sufficiency as we journey together. Have a stable job and be financially independent. (As financially independent as one can be in this economy)

  11. Monogamous Commitment: In our love story, there’s no room for extras—just us.

  12. Freedom from Addictions: Cherish health over habits. Avoid smoking, heavy drugs, heavy drinking, or excessive video gaming.

  13. Open Communication: Let’s be fluent in the language of our hearts, expressing desires, wants, needs, expectations, and dreams without hesitation.

These expectations help me find someone who aligns with my values and lifestyle, creating a healthier and more fulfilling relationship.

The Rollercoaster of Dating Apps and Online Dating

Dating in your 40s, especially online, is like riding a rollercoaster in the dark—blindfolded, with a belly full of bad carnival food. The dating pool? It’s a murky swamp filled with frogs, and some are way worse than others.


Welcome to my world of “practice dates.” These are first dates with men freshly ejected from long-term relationships, where I play love coach. It’s Dating 101: “Swipe Right and Hold On Tight.”

These practice dates are a blast because I get to channel my inner teacher, guiding these clueless newbies, sharing my own disaster dates, and showing them the lay of the land. My top advice? Be honest.

If you’re just looking for a hookup, own it. There’s nothing worse than a guy pretending he wants a serious relationship when he’s really just auditioning for “America’s Next Top Player.”

Now, let’s dive into the great height hoax. I call it “Tinder Tall” vs. “Real Height.” The number of men fibbing about their height on dating apps is astounding. One guy claimed to be six feet tall, but I could see eye to eye with him—literally.

Another dude said he was 5’9”, yet his head barely reached my nose. Even the genuinely tall ones are like, “Whoa, you’re taller than I expected!”

One guy, a carpenter, actually offered to fetch his measuring tape. Seriously, I don’t mind being taller—I’m 5’10” with a personality to match. Confidence is what counts. Add some heels and my hair, and I’m about six foot.

A few inches shorter? No problem. But please, don’t act shocked when you meet me after I’ve already told you my height.

Sometimes Dating in Your 40s Feels Like a Hamster Wheel

Then there’s the Groundhog Day phenomenon of online dating. All the apps have the same cast of characters, whether you pay or not. I take breaks, but the same profiles are popping up six months later, like a bad sequel.

If they haven’t changed, neither have I. It’s like a dating déjà vu nightmare. And let’s face it—the dating pool often feels like it has pee in it.

In our fast-food dating culture, everyone’s searching for the next best thing, treating people like disposable forks. Add being in your 40s to the mix, and it’s even tougher.

Living in a huge but sparsely populated state doesn’t help.

But I refuse to be disposable. I’m focusing on myself, being resilient, and finding the right person organically. Maybe I’ll wander around hardware stores, as my son suggested, or visit the tractor and feed stores.

My daughter jokingly said I should become a principal and call in all the single dads. Jokes aside, I never discuss my dating life with my kids. They gave the advice because they sometimes worried about me being single. So, they offer random advice once in a while. 

Two years ago, my daughter, out of the blue, told me to date women because I obviously wasn’t going to meet a guy.

They’ve NEVER met any guy in the past six years, not even male friends. They don’t need that drama. I see what it does to my students, and it breaks my heart. I’m a mom, first and foremost.

Humor and Optimism in the Face of Absurdity

Through all the absurd experiences I have had while dating in my 40s, I remain optimistic. I know I’m not perfect—I’m honest and maybe a bit too blunt—but I stay true to myself. I’m determined to find the right person who gets me.

Online dating is now the norm, but it comes with its own headaches. Did you know 30% of Tinder users are married, and another 12% are in a relationship but still on the app? It’s like shopping for fresh produce and discovering half the fruits are plastic.

The dating app circus is so repetitive that my friends and I have started giving code names to the guys we meet based on their looks or personalities. There’s “Hot Dad,” “Viking,” and “Milk Toast.”

I can only imagine what names guys come up with for me. With my car’s eyelashes and my literal nature, they probably call me “Miss Frizzle’s Taller Sister” or maybe “Tattooed Amazon.” Honestly, I’d be flattered if they even got that creative.

Embracing Challenges and Pursuing Passions While Dating

In conclusion, my journey as a resilient, independent woman at 40 has been about embracing challenges, finding strength in adversity, and pursuing my passions with unwavering determination.

From navigating the complexities of dating to facing the stages of grief after my divorce, I’ve learned valuable lessons about self-love, boundaries, and resilience.

Through it all, I’ve surrounded myself with supportive communities, sought wisdom from like-minded individuals, and remained true to my values and beliefs.

As I continue on this journey of dating in my 40s, I carry with me a clear vision of what I want in a partner and what I expect from myself, ensuring that my path forward is guided by resilience, self-assurance, and the courage to define my own success.

If you are having trouble meeting people online, dating after divorce, or want to share funny dating stories, please leave a comment below! 

1 thought on “Dating in Your 40s: A Journey of Strength and Self-Love

  1. Barb

    I dated a boy after my divorce in my 40s but gave up trying. I used to say that guys couldn’t even see the gene pool from where they were. Eventually, I did meet someone and lived again until he passed way too soon. The dating pool in my 60s is so much worse, and seems like too much work.
    Hoping you meet someone fantastic for you.


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