Dating in Midlife: A Journey of Self-Discovery, Awkward Moments, and Hope

Does this sound familiar?

Raise your hand if you got married in your early twenties, divorced in your late forties, and are now diving into the dating scene for the very first time. Yep, that’s me—navigating the uncharted waters of modern dating with a mix of curiosity and trepidation.

From Cornfields to Coffee Dates

When I was 17, I met the man who would become my husband of 19 years. Dating before him? Minimal. Online dating? Nonexistent. Back then, we actually had to go out and meet people—think parties in cornfields or hanging out at the local bowling alley. Needless to say, my dating experience was limited.

Fast forward through one wedding, two wonderful children, and a 19-year marriage that eventually ended in divorce. Not knowing how to be alone, I quickly jumped into another long-term relationship, skipping the whole “single and ready to mingle” phase. A few years later, that relationship ended, leaving me single for the first time as an adult and facing the daunting prospect of dating.

Lessons Learned

From these relationships, I’ve gained clarity about what I want—and, more importantly, what I don’t. I want a partner who is smart, funny, and driven. I don’t want someone with unresolved addictions or complicated relationships. My children are grown, and I’m ready for a partner who adds to my life, not one who takes away my peace, self-worth, or independence.

Starting From a Solid Foundation

Before jumping back into the dating world, I made the decision to focus on me. For over six months, I dedicated time to healing, reflecting, and rediscovering who I am outside of a relationship. It wasn’t easy, but it was necessary—and empowering.

I reconnected with my faith, creating a foundation of peace and purpose in my daily life. I built a life that feels independent and fulfilling—a life I truly love. Financially, I’m secure with a career I’m proud of, and emotionally, I’m surrounded by a small circle of supportive, loving women who remind me of my worth on the days I need it most.

Most importantly, I’ve learned to find contentment within myself. I don’t need a relationship to feel whole. I’ve embraced who I am, what I want, and what I deserve. If you’re in a place of self-discovery, know this: taking time to focus on yourself isn’t just okay—it’s one of the most powerful things you can do.

Entering the Dating Scene

With a mix of optimism and a little naivety, I decided it was time to dive into dating. I pictured fun dates, meaningful conversations, and the start of an exciting new chapter. After a few organic meetups, I figured I’d try online dating—it seemed like the easiest way to meet new people. Facebook Dating was free and already on my phone, so I thought, why not?

Before diving in to create a profile, I took some time to make a  list of the values I wanted in my future partner and how I wanted to be treated. I also made a list of the things I know I don’t want. (I’ll share in a bit how that came in handy for me.) 

I put serious thought into crafting my profile, making sure it reflected exactly what I was looking for. Before I knew it, I was matching with a few people and setting up my first coffee date. (Pro tip: Coffee dates are the way to go for online matches! They’re quick, low-pressure, and easy to exit if the vibe isn’t right. No one wants to be stuck enduring a full dinner with someone they don’t click with!)

Since then, I’ve had some unforgettable experiences. I’ve gone fly fishing, attended one of the most amazing concerts of my life in Vegas, hiked beautiful trails, sipped wine at tastings, and even navigated a corn maze. I’ve had deep conversations about life, kids, relationships, and have a deeper appreciation for other’s life experiences. Along the way, I’ve heard way too many stories about exes (seriously, it’s a thing), but I’ve also been called beautiful, intelligent, funny, and intimidating (which I don’t quite understand…I’m 5’2” tall!).

Remember that list of values and traits I’m looking for (and avoiding) in a partner? I revisit it before and after every date. After each outing, I take time to journal and reflect—not just on what we did, but on how he made me feel about myself and how closely he aligned with the qualities I’m seeking.

This practice has been an incredibly powerful tool for self-reflection. It’s helped me stay grounded, gain clarity, and learn more about myself throughout this journey.

Seven months into this experience, I haven’t found “the one” yet, but I’ve found something just as important: a deeper understanding of myself. Each date, each story, and each adventure has taught me more about what I value, what I’m looking for, and what I refuse to settle for.

What I’ve Learned

Dating in your late forties is an entirely different ballgame. While attraction is still important, it’s no longer just about looks. It’s about how someone treats me and how they make me feel about myself. Does he open doors (car doors are a plus!)? Does he ask thoughtful questions to get to know me? Does he align with my values?

I’ve had some awkward encounters, but I approach every interaction with hope and an open heart. I’ve learned what truly matters to me and what doesn’t, and I’ve grown more confident in my ability to recognize red flags and stand by my boundaries, something I have not historically been great at!

One of the most important things I’ve learned is to always show up authentically and give others the space to do the same. Showing up authentically in dating means embracing who you truly are—flaws, quirks, and all. It creates space for genuine connections and ensures you attract someone who loves you as you are, not an idealized version. Authenticity may feel vulnerable, but it’s the foundation of trust and true connection.

I’ve learned the importance of speaking my truth early on. This means being upfront about how I feel about the connection and gradually sharing the messy, real parts of my life—maybe not on the first date, but definitely by the second or third. It’s not about oversharing; it’s about respecting both your time and theirs by being honest and authentic. The sooner you show who you really are, the sooner you’ll discover if the connection is truly worth pursuing.

Staying Hopeful

Dating can be exhausting, and I’ve taken breaks when needed. A friend recently asked how it’s going, and while I joked about the challenges, I’m committed to finding the right person. I’m not in a rush, and I refuse to settle.

They say love happens “when you least expect it.” So, for now, I’m focusing on living my best life, keeping my heart open, and trusting that the right person will come along in time.

Final Thoughts

Dating at this stage in life isn’t easy, but it’s also an incredible opportunity for self-discovery. If you’re in the same boat, remember—you’re not alone. I’ve been there, babe! Take it one step, one date, one moment at a time. Stay true to yourself, and don’t forget to embrace the experience along the way.