Making Connections, Part 4: Practicing Deeper Conversations
Estimated reading times: 3 minutes
So you’ve made it past the small talk. Now what?
This is where a lot of people freeze. The fear is real: What if I overshare? What if it gets awkward? What if they don’t want to go deeper?
The good news: deeper conversations aren’t about being profound — they’re about being responsive.
Recognize When Someone’s Open
Connection is a two-way street. Look for signs they’re willing to keep going:
They give more than one-word answers.
They ask follow-up questions.
Their body language is open — facing you, making eye contact, leaning in.
If those aren’t there? Keep it light. Not every interaction needs to turn into a heart-to-heart.
What Keeps Momentum Alive
Layer your questions. If they mention travel, don’t stop at “Where did you go?” Ask, “What made that trip memorable?”
Match their energy. If they’re playful, join in. If they’re reflective, slow down with them.
Share back. A little self-disclosure keeps the exchange balanced.
Avoid the “Interview Trap”
Rapid-fire questions can make someone feel like they’re on the spot. Instead, try weaving in your own experiences:
Instead of: “What do you do for work?”
Try: “I’ve been juggling a lot at work this week — how’s it been for you?”
This way, you’re not just extracting information — you’re trading pieces of your world.
Final Thoughts
Practicing deeper conversations isn’t about perfect timing or flawless delivery. It’s about noticing when the door is open, stepping through with curiosity, and bringing something of yourself along.
Making Connections is an ongoing series about where and how to meet people, move beyond small talk, and build real relationships.
Next up in this series: Part 5: Building Habits & Social Confidence.
