Is Your Dating Style Actually Blocking Real Connection? Debrena Says It Might Be

In her latest Love Lab segment on Back2Besa, relationship coach Debrena Jackson Gandy delivers a powerful reality check: most of us aren’t actually getting to know the people we’re dating—we’re just measuring them against a checklist.

“Dating, as we’ve been doing it, has not been about getting to know a man,” Debrena says. “It’s been about scorecarding him against a list in our heads.”

She explains how many women fall into the trap of asking “biography” or surface-level questions—like where he works or where he went to school—when what we really want are insights into his values, his spirit, and his life experiences.

“If we were truly trying to get to know a man,” Debrena says, “we’d be much more present. We’d be asking questions that reveal character and depth.”

Here are a few examples of Debrena’s deeper-dive dating questions:

Instead of: “What do you do for work?”

Try: “How did you come to be interested in that line of work?”

Instead of: “Where did you grow up?”

Ask: “What are two life lessons that have made you a better person, and how?”

These types of questions don’t just fill space—they open up the opportunity to truly understand someone’s journey, worldview, and inner makeup. And according to Debrena, that’s where real connection begins.

As she closes the segment, she encourages viewers to be intentional and practice this new way of connecting:

“Are you picking up what I’m putting down? Now it’s your turn—go ahead and practice, practice, practice.”

You can catch The Love Lab with Debrena as part of Back2Besa on FOX Soul, where every segment is packed with fresh tools for building juicy, meaningful love. For more Debrena, head over to her website at milliondollarmentor.net