If Real Talk Could Talk

The Value of Discussions

Sometimes, I really enjoy conversations that involve an exchange of ideas and differing perspectives.

To be clear, I’m not talking about arguments, and in my view, the conversations I’m referring to don’t even reach the level of debates.

I’m talking about discussions—conversations that go a bit deeper than surface-level small talk, the kind that tend to reveal our true personality and character.

For example, I might ask:

• Where do you see yourself living long-term?

• Why did your last relationship end?

• When was the last time you spoke to God?

Of course, this isn’t an exhaustive list. But questions like these require a certain level of vulnerability, and this kind of openness can help a relationship grow.

But not everyone is well-equipped for these kinds of discussions. Insecurities, ego, and unresolved trauma can take the soul hostage. Genuine curiosity is often met with defensiveness, bitterness, or resentment.

The purpose of these conversations isn’t to judge, shame, or embarrass. It’s to better understand each other—to create a foundation of trust and deeper connection.

The Brunch Date That Went Sideways

Quick story: Some time ago, I planned a brunch date in Chicago with a woman who lived in Dallas. Technically, it was our second date.

On paper, she was a real catch—beautiful, with a warm voice, a similar cultural background, and a strong sense of ambition.

The date was going well overall. We enjoyed the food and had a pleasant conversation about places we’d consider living. Our plates were nearly clean when I asked, “So, how many relationships have you been in?”

“Three,” she said plainly, after a brief pause. “One in high school, one in college, and one after grad school.”

“I see,” I replied. “Why didn’t they work out?”

She explained that the high school relationship ended because they were heading to colleges in different parts of the country. The post-grad one ended for similar reasons—life taking them in separate directions.

The Ex Who Must Not Be Named

It was the college relationship that caught my attention. She mentioned she had been in a long-term relationship with a football player who was later drafted into the NFL. I knew she had attended a well-known NFL feeder school for undergrad. As a football player myself, my curiosity was piqued.

“Really? Would I know who this person is?” I asked.

She didn’t flinch. “Yes,” she said.

I thought to myself, Well, that’s interesting.

My curiosity deepened, not out of judgment, but out of a genuine desire to understand where she was coming from.

“Well, may I ask who it was?” I asked as gently as I could, with a grin.

Her demeanor shifted. She became uncomfortable, defensive even.

She didn’t want to talk about it.

I found it odd. She had been comfortable enough to mention that one of her exes was an NFL draft pick, and that I would likely know who he was.

But for some reason, she wasn’t ready to say his name.

Here was my thought process: If we’re seeing each other romantically, we might as well get this bit out of the way. No need to build it up into something dramatic later. Besides, we were long distance. We didn’t have the luxury of spending time together regularly, so I valued the chance to connect meaningfully while we could. Just rip the Band-Aid off.

It became clear this was a soft spot for her and maybe she hadn’t fully moved on. But that struck me as strange. She had graduated undergrad years ago and had even been in another long-term relationship since then.

Our conversation went off the rails. Her energy shifted. She grew more animated, even tapping the table to underline her points. She called me “combative” and “argumentative.” She said I only liked to engage in conflict because I’m a lawyer. I was caught off guard. All I really wanted to know was why she didn’t want to share.

Final Thought

Here’s what this brunch date taught me:

Meaningful conversations require two things: genuine curiosity and a respect for personal boundaries. Without both, even well-intentioned questions can feel like attacks, and honest answers can be withheld.

I recognize that my own tone can sometimes come across as blunt or direct, and that’s something I’m working on. But at its core, honest dialogue is about connection, not confrontation.

If we shy away from honest questions or dismiss vulnerability with defensiveness, we risk stalling the growth of any relationship, romantic or otherwise.

Ultimately, I think true connection comes when we can talk openly, listen deeply, and hold space for each other’s discomfort without judgment.

That’s the kind of conversation I hope we can all strive for.

Looking forward to hearing your thoughts. See you in July.