My Dating After 40 Tips: Rediscovering Myself in Love

Let me tell you a little story. Once upon a time, there was a woman (okay, it’s me) who thought she had this whole dating thing figured out. Spoiler alert: she didn’t. But in my defense, I wasn’t exactly looking for my soulmate; I was busy hunting for a father figure. Yep, you heard that right. My dating radar was set to “Dad Material,” and let’s just say, it was a hot mess.

I spent a good chunk of my life focused on being a mom and aunt. Roles I cherished more than anything. So naturally, when I was dating, I wasn’t thinking about what I wanted. I was vetting men like a casting director for the role of “Perfect Father Figure.” It didn’t matter if they snored louder than a freight train or had the charisma of a stale cracker. If they seemed like they could help my son with his homework or give a decent dad joke, they were in the running.

The Great Emotional Sabbatical and Situationships

Fast forward a bit, and I realized that maybe, just maybe, I was doing this whole dating thing incorrectly. Sure, finding a good dad is important, but what about finding someone who’s good for me too? This lightbulb moment coincided with a period I like to call “The Great Emotional Sabbatical.” For 12 long years, I was single but not really “dating.” Instead, I got myself entangled in what the cool kids now call “situationships”. Those in-between places where you’re not quite in a relationship but not exactly single either. Think of it as the relationship equivalent of being stuck in a traffic jam. You’re moving, but you’re not getting anywhere.

Why, you ask? Well, I wasn’t into introducing a revolving door of men into my son’s and nieces’ lives, and I still hadn’t quite figured out what I wanted. So, situationships it was! Safe, no commitments, and just enough company to not feel completely alone. But then came the last situationship that lasted a whopping five years. Yep, five years of “What are we?” until I finally realized that I was ready for more, and he wasn’t. Cue the violins.

Love, Loss, and Learning to Trust Myself Again

Ending that situationship was tough. I mean, I thought I was in love with the guy, then I thought, maybe I was more in love with the idea of being in love. You know how it goes—you want so badly to be loved that you’re willing to overlook the fact that your “partner” might be as emotionally available as a brick wall. And here’s the kicker: I started doubting myself. Was I capable of choosing the right partner? Were my best years behind me? Was I doomed to be that woman with a dozen cats and a Netflix subscription?

And don’t even get me started on the insecurities. My judgment in men was shot, my confidence took a nosedive, and let’s not forget the whole aging thing. It’s like one day you’re this vibrant, confident woman, and the next, you’re examining every mole, every gray hair, wondering if you’re still “desirable.”

Adding to the Insecurities: Pee in the Pool

And speaking of insecurities, let me share a little story that didn’t exactly help my confidence in the dating scene. Anyone with natural hair knows it’s not just hair—it’s an event, a ritual, a whole thing. So there I was, dedicating an entire Saturday to my wash day routine. Six hours later—yes, six—I had shampooed, deep-conditioned, detangled, and styled my hair into what I thought was a fabulous twist-out. I was feeling myself and thought I looked great.

Then, this guy (not the five-year situationship, just to clarify) come to pick me up, takes one look at my hair, and asks, “Are you going to do your hair?”. Excuse me, ninja whet?! I had just poured hours of care into my hair, and his comment hit me like a ton of bricks. It was another layer of doubt added to the already complex world of dating. It made me question, yet again, if I was enough—just as I am.

But here’s the thing: moments like this have taught me that I need someone who sees all of me—the good hair days, the bad hair days, and everything in between. If a man can’t appreciate my natural curls after a six-hour wash day, how will he handle the real me, with all my complexities and quirks?

Navigating Situationships: Understanding What You Really Want in Dating After 40

As I re-entered the dating world after 40, I realized that building confidence was key. I had to redefine beauty standards for myself, embracing my natural hair and setting healthy dating boundaries. I had to let go of what others expected and focus on what I truly needed. This meant leaving behind the safety net of situationships and stepping into a space where my needs were at the forefront.

Building Confidence for Dating After 40: Embrace Your Natural Beauty

So, what’s a girl to do? Well, after taking a good, hard look at myself (and maybe a few pints of ice cream), I decided it was time to get back out there, but with a twist. This time, it’s all about me. No more looking for a dad. No more settling for situationships. I’m dating with intention, people!

And here’s what I’ve learned so far on this new journey and my dating after 40 tips:

1. Know What You Want: Seriously, take some time to figure out what makes you happy. Not what makes you comfortable, or what you think you should want, but what actually brings you joy. For me, it’s someone who appreciates my sense of humor, loves my natural hair, and knows the difference between a Pinot Noir and a Cabernet Sauvignon (okay, maybe that’s asking too much).
2. Set Your Boundaries: If someone isn’t willing to meet you halfway, then honey, it’s time to keep walking. Life’s too short to waste on people who don’t see your worth. And remember, “No” is a complete sentence. Use it often and with conviction.
3. Have Fun With It: Dating should be fun! It’s not a job interview (though it might feel like it sometimes). It’s about meeting new people, having new experiences, and maybe finding someone who makes your heart skip a beat. So, let go of the pressure and just enjoy the ride.
4. Embrace Your Fabulousness: Look, we all have insecurities. But there’s also a whole lot of fabulousness going on that we need to acknowledge. So, your body’s changed a bit—big deal! Confidence is the most attractive thing you can wear. Own it!

The Journey Continues

So, here I am, stepping back into the dating world with a lot more wisdom, a bit more confidence, and a sense of humor about it all. It’s not about finding someone to complete me—it’s my job to make myself whole. It’s about finding someone who complements my fly. And I know it’s out there, waiting for me. Until then, I’m just going to keep enjoying the journey, one date at a time.

And hey, if you’ve been on a similar journey, I’d love to hear your story. What’s been your biggest lesson in love and self-discovery? Do you have any dating after 40 tips to share? Let’s chat in the Facebook group!

Two resources I found helpful for Women Over 40 Navigating the Dating World

Navigating dating after 40 can feel daunting, but there are plenty of resources out there to help you rediscover your confidence and joy:

1. Dating After 40: Tips for Finding Love Again – This article provides practical advice for dating later in life, focusing on self-awareness, setting boundaries, and enjoying the process without pressure. Perfect for those re-entering the dating scene after a long break.
2. How to Date Confidently After 40 by Susan Winter – A video from relationship expert Susan Winter offering tips on dating with confidence after 40, highlighting self-love, authenticity, and maintaining high standards.