Name: Poise - AI Dating Coach
Author: Poise

You've been chatting for days. You know what they do for work, where they're from, what they did last weekend. But you still have no idea who they actually are.

Small talk is the enemy of connection. Here's how to move past it.

Why We Get Stuck in Small Talk

The Default Mode

Small talk feels safe:

No risk of oversharing
No vulnerability required
Can be done on autopilot
Doesn't reveal much either way

But safety isn't the goal. Connection is.

The Fear Factor

Going deeper feels risky:

What if they think my question is weird?
What if I reveal too much?
What if the conversation gets awkward?
What if we're not actually compatible once we go deeper?

These fears keep us surface-level—and disconnected.

The Pattern

Typical dating app conversation:

"Hey!"
"Hey! How are you?"
"Good, you?"
"Good! How was your day?"
"Pretty good, worked and watched some TV. You?"
[This continues indefinitely]

No one is actually getting to know anyone.

The Shift: From Information Exchange to Connection

Small Talk vs. Meaningful Conversation

Small talk:

Exchanges facts
Could be said to anyone
Stays surface-level
Avoids anything personal
Doesn't require thought

Meaningful conversation:

Explores experiences, values, perspectives
Is specific to this person
Goes beneath the surface
Reveals something about both people
Creates genuine interest

The Goal

Move from:

"What do you do for work?"

To:

"What's something you're working on right now that you're excited about?"

Same general territory; completely different depth.

Strategies for Going Deeper

Strategy 1: Ask "Why" Questions

Instead of what, ask why:

Surface: "What's your job?" Deeper: "What drew you to that field?"

Surface: "What do you do for fun?" Deeper: "What's something you've been wanting to try but haven't yet?"

Surface: "Where are you from?" Deeper: "What's shaped who you are from where you grew up?"

Strategy 2: Follow the Energy

When they mention something with energy, pursue it:

Them: "I just got back from a really interesting trip."

Surface response: "Cool, where did you go?" Deeper response: "What made it interesting? What stuck with you?"

Notice what lights them up and explore it.

Strategy 3: Share to Invite

Share something meaningful to create space for them to share:

"I've been thinking a lot about [meaningful topic] lately. It's made me realize [insight]. What's been on your mind recently?"

Your vulnerability invites theirs.

Strategy 4: Ask Opinion Questions

Request their perspective:

"What's your take on [topic related to something in their profile]?"

"I'm curious what you think about [interesting dilemma]."

Opinions reveal values, personality, and how they think.

Strategy 5: Explore Rather Than Interrogate

Don't rapid-fire questions. Explore one topic deeply:

Bad:

"What do you do? Where are you from? What do you do for fun? What are you looking for?"

Better:

"You mentioned you're into photography. What draws you to it? What kind of stuff do you shoot? What's the most interesting thing you've photographed?"

Depth on one topic beats breadth on many.

Questions That Go Deeper

About Interests and Passions

"What's something you know a lot about that you could talk about for hours?"
"What's something you're working on right now that you're excited about?"
"What would you do if you had more time and money?"

About Values and Perspectives

"What's something you've changed your mind about recently?"
"What matters most to you in your relationships?"
"What's a value you hold that surprises people?"

About Experiences and Stories

"What's a moment that changed how you see the world?"
"What's the most interesting thing you've done this year?"
"Tell me about a time when you surprised yourself."

About Dreams and Desires

"If you could wake up tomorrow with a new skill, what would it be?"
"What's something on your 'someday' list?"
"What would your ideal week look like?"

About Connection and Relationships

"What makes you feel most connected to someone?"
"What's the best conversation you've had recently?"
"What does good communication look like to you?"

Reading Their Response

Signs They Want to Go Deeper

They give thoughtful, longer answers
They ask similar questions back
They share personal stories or opinions
They seem engaged and curious

Your move: Keep going deeper. This is working.

Signs They're Not Ready

Short answers that don't invite follow-up
Deflecting with humor
Changing the subject
Answering but not asking back

Your move:

They might need more warmth first
Try a different topic
Or accept this might not be a deep-conversation person

Signs of Incompatibility

They actively resist deeper questions
They seem annoyed by your curiosity
Every attempt at depth falls flat
The conversation stays shallow no matter what

Your move: This person may not be right for you if connection is what you're after.

When to Go Deep vs. Stay Surface

Start Surface, Then Go Deeper

You don't need to open with existential questions. A common pattern:

Message 1-3: Basic introduction, confirming mutual interest Message 4-10: Moving toward more interesting topics Message 10+: Genuinely deeper conversation if chemistry exists

Reading the Room

Good times to go deeper:

They're engaged and curious
The conversation has momentum
There's already some rapport
They've shared something personal

Maybe stay surface:

Very early in the conversation
They seem stressed or distracted
The tone is light and playful
You haven't established comfort yet

Calibrating

Different people have different comfort levels with depth. Some want to go deep immediately; others need more time. Pay attention to what they respond to best.

If You're Bad at Small Talk

Embrace It

Maybe surface conversation isn't your strength. That's okay:

"Fair warning: I'm terrible at small talk but great at actual conversation. Want to skip to the interesting stuff?"

Some people will appreciate this.

Use It as a Filter

If someone only wants small talk and you need depth, you're probably not compatible. Better to find out early.

Give Yourself Permission

You don't have to be good at everything. You can be the person who goes deeper faster. The right people will appreciate it.

Moving to Meeting

Deep Conversation ≠ Endless Conversation

Good conversation should lead somewhere:

"I've really enjoyed talking to you. This is the kind of conversation that would be even better in person. Want to meet up?"

Don't use depth as a substitute for actually meeting.

What Deep Conversation Tells You

By going deeper, you've learned:

Whether you actually want to meet this person
Whether you have genuine connection potential
What you'd talk about on a date
Whether they're interested in the same kind of relationship

FAQ

What if my deeper questions seem too intense? Frame them casually. "I'm curious..." or "Random question..." softens the intensity. Also, some people want intense conversation—this filters for them.

What if they don't reciprocate depth? Give them a chance by leading with your own sharing. If they still don't go deeper, they might not be capable of (or interested in) that level of conversation.

Can you have too deep a conversation over text? Sometimes. If you're having hours-long philosophical exchanges but never meeting, something's off. Use depth to assess compatibility, then meet.

What if I'm not sure what to ask? Listen to what they say and get curious. The best questions emerge from genuine interest in their answers.

Related Guides

Connection Requires Courage

Going past small talk means risking awkwardness and showing interest. Poise can help you find questions and conversation starters that lead to real connection.

How to Move Past Small Talk on Dating Apps (2026)