A little while ago, I casually announced something that felt anything but casual to me: I’m officially dating again.
Cue dramatic music. 😅
After being married for 19 years, going through a divorce, dating for three years, and then being engaged for another year, I finally felt ready, actually ready, to venture back into the adult dating pool. No floaties. No lifeguard. Just me, my lived experience, and a whole lot of self-awareness.
So far, my re-entry point has been the Facebook Dating app. I haven’t ventured beyond it, and honestly? It’s been… surprisingly pleasant. I’ve gone on a handful of dates with genuinely kind, respectful men. No horror stories yet (knock on wood). I haven’t found “the one,” but that hasn’t been the point. What I have found is something unexpected: myself, again and again, through each interaction.
I know that sounds a little strange, but hear me out.
Every conversation, every text exchange, every phone call, and every in-person date has inspired me, challenged me, or taught me something about life, relationships, perspective, and my own growth. I’ve learned to pause and reflect, not just on why something may not work, but on who this person is, how they see the world, what matters to them, and what I can take away from that encounter.
I truly believe it’s a privilege when someone invites you into their life, especially when they offer you their time. Even more so when they share vulnerable pieces of their past. I don’t take that lightly. I value each interaction, and I’m genuinely grateful for every person who’s crossed my path, even briefly.
And what’s wild is how none of it feels coincidental. The timing of conversations. The lessons that show up right when I need them. The insights gained from what someone does for a living, how they live, a cultural tradition they share, or even a food I’d never tried before. Dating has become less about “finding someone” and more about being present and making the most of what shows up.
That said… let’s talk about the observations. Because oh, there are observations.
Observation #1: Is There a Secret Guy Photo Rulebook?
Let’s start with the humor. When I created my dating profile, I had no idea what to expect. I’d heard plenty of horror stories, so I braced myself. Thankfully, the men I’ve connected with so far have been refreshingly normal.
But I couldn’t help but notice a pattern.
Why does almost every guy have:
- A picture at the gym
- A picture in a boat or car
- And a picture with their dog
Is there a monthly newsletter they all subscribe to? 😂
It’s not a bad thing, just endlessly entertaining.
Observation #2: Dating Has Made Me Appreciate My Life More Than Ever
One man shared that he had always dreamed of a big family and a stay-at-home wife, but life didn’t unfold that way. He ended up with one child and a wife who returned to work shortly after their child was born.
That conversation stopped me in my tracks.
For years, I’ve questioned my career trajectory, my finances, and whether I “should be further along” by now. But in that moment, I realized how profoundly blessed I am. I stayed home and raised my children when they needed me most, and I would never, not once, regret that decision. My children wouldn’t be who they are today, and I wouldn’t be who I am, without that chapter.
Another gentleman opened up about lifelong health issues he manages daily. It instantly reframed some of my own worries. Suddenly, concerns I’d been carrying felt shallow. I was reminded to be grateful, for my health, my body, and this season of strength I often take for granted.
Observation #3: Even Successful Adults Are Still Carrying Insecurities
This one surprised me the most.
Men who are accomplished, financially secure, and respected in their careers still wrestle with deep insecurities. Trying to prove themselves to a father who never showed up. Wanting validation. Longing to be seen and accepted for who they are, not just what they’ve achieved.
It turns out, adulthood doesn’t magically erase old wounds. We all carry something.
Lessons Learned (a.k.a. Things I’m No Longer Ignoring)
One of the most valuable lessons I’ve learned while dating again is simple but powerful: watch actions, not words.
If someone says they’re direct and straightforward but communicates vaguely, pay attention.
If someone claims to be a gentleman but doesn’t act like one, red flag.
The beauty of dating at this stage of life is being able to spot these things early, without investing months, or years, before the truth reveals itself.
And let’s be honest: by middle age, we all have baggage. Some people are upfront about it. Some even present their own “diagnosis” early on. And you know what? I respect that honesty.
And this is something I think many of us need to hear, especially when loneliness tempts us to revisit the familiar instead of choosing growth.
“Give yourself the chance to meet someone new. Don’t go back to someone who was lucky enough to have you but didn’t value you.”
Where I Am Now
I’m enjoying my life. I’m having fun. I’m learning about others, and myself. And most of all, I’m deeply appreciating the life I’ve built.
As women, we can have it all, just not all at once.
Maybe I did things out of order. I married. I stayed home. I became a working mom. I went back to school. And now? I’m dating.
And I can honestly say, I’ve never been happier.
I no longer worry about what others think of my choices. I feel comfortable in my own skin. I know my worth, and I refuse to settle. I’m still a hopeless romantic, and I believe my person is out there.
I trust God’s timing. And until then, I’ll keep enjoying my life, meeting new people, and learning along the way.
So tell me,
Is anyone else in a similar boat? Did this resonate with you?
Mom on the go in Holy Toledo 