I have a date scheduled for tonight. And as I sit here, I’m realizing something that I’ve joked about for a while, but now I’m saying it with quiet, serious earnestness: I don’t know the first thing about dating or relationships.
Maybe I never did. Maybe that’s the point.
I’ve spent months on this blog and on my podcast talking about how my past relationships were often fueled by chemistry, attraction, and an eagerness to, quite frankly, just get in each other’s pants. I recently closed the chapter on a relationship that ended when I realized my partner had no intention of taking things beyond a junior high school level of commitment.
Now, I’m operating in what I’ve been calling “third gear”—my own “Goldilocks” version of dating: not too hot, not too cold, just right.
The Binary Trap
The problem is, I’m finding myself in direct conflict with every instinct and desire I once held. I’m battling the binary extremes I used to live by. Previously, I dove headfirst into the honeymoon phase only to find that when the fire died, there was no foundation underneath our feet. This most recent time, I played it cool, stayed casual, and told myself I didn’t want anything exclusive. Then the lightbulb went off: after 18 months, “casual” had become a trap.
I don’t know how to proceed, but I know there is a middle ground.
Choosing Myself
I’ve come to realize that this “middle ground” is a dual-purpose endeavor. It is a necessary protection for my own peace, but more importantly, it is a statement of self-respect. It’s frustrating, because my past experiences have left me with a mental list of “don’ts.” But I’m learning that the goal isn’t to follow a list—it’s to be 100% myself.
The First Date Strategy
I realized today that showing up as me is far more important than any specific outcome. I don’t need to force a result. I’m just going to go there and be “First Date Rob.” I don’t like to brag, but I know who I am, and I know that I’m a pretty damn good first date—because I can back that up.
There are already some promising green flags. I offered to drive out to her; she chose the restaurant and made the reservation. She even offered to let me pick her up at her house—a level of hospitality that is almost unheard of in this day and age.
We’ve known each other for a few years now, meeting on an app long before the timing was right. We stayed in touch via social media—talking about our kids, politics, and the occasional exchange of Tigers tickets. I’ve always thought she was a cool person. And even when she was with someone else, I genuinely reconciled that fact because I respected who she was.
Now, I realize I’m interested in her as a person, period. And while that might fly in the face of my own long-held belief that men and women can’t be purely platonic without some underlying attraction, I’m okay with that nuance.
In about 12 hours, I’ll have my answer. But for the first time in a long time, the answer I get isn’t the most important thing. Showing up as my authentic self is.
P.S. If you missed this morning’s post on the “Sleepless Knight” and my struggle to find rest, you can catch up here. It’s all part of the same work in progress.
Rebuilding a life takes grit, consistency, and a lot of ‘Option C’ thinking. Having crossed the 1,000-day milestone, I’m now charting the territory beyond. The mission remains the same: No glitz. Just the work. New to the blog? Start your journey here to see the blueprint and the ‘Tricorder’ perspective behind the rebuild.
Today’s post is inspired by the WordPress Daily Prompt. While I’ve taken the topic in my own direction for the Road beyond 1,000 Days, you can find more responses to today’s prompt HERE.
Thanks for stopping by Rebuilding Rob. Be sure to like 👍, comment and subscribe below. It’s greatly appreciated! Also, feel free to follow me on social media and check out my recent posts!
- The Hamlet of the Comic Book Genre: The Psychology of the Dark Knight
- My dinner with the Dark Knight Detective
- Rob Reviews: Star Trek: Strange New Worlds season 4, episode 1 “Valles Marineris”
- Priceless: Why College Was My Best Purchase (Even If I’m Still Paying For It)
- The Legend of the Street Fight
AI art created by Google Gemini
The article “The Middle Ground: Navigating the Audacity of Potential” first appeared on Rebuilding Rob


Leave a Reply