Everyone wants deeper conversations. Nobody wants to be the person who forces them. There’s a reason “let’s skip the small talk” feels cringe even though the sentiment is right. Depth can’t be demanded. It has to be invited.
The good news: it’s easier than you think. You don’t need to transform into a therapist or turn every dinner into an emotional seminar. You need one skill, one habit, and a willingness to go first.
Why most conversations stay shallow
It’s not laziness. It’s safety. Small talk exists because it’s risk-free. “How was your weekend?” can’t be answered wrong. Nobody gets hurt. Nobody gets surprised. And nobody leaves feeling known.
The problem is that we mistake safety for connection. We think if a conversation feels comfortable, it must be going well. But comfort and connection are different things. Connection requires a little discomfort — the productive kind, where you say something you haven’t rehearsed.
A comfortable conversation keeps the friendship where it is. A slightly uncomfortable one moves it forward.
The one skill: ask specific questions
The single biggest lever for deeper conversation is the specificity of your questions. Generic questions get generic answers. Specific questions unlock real ones.
Compare these:
Generic: “How are you?”
Specific: “What’s been taking up most of your mental energy lately?”
Generic: “How’s work?”
Specific: “What’s something at work that’s been bothering you that you haven’t told anyone?”
Generic: “What’s new?”
Specific: “What’s something you’ve changed your mind about recently?”
The specific question does three things: it signals that you actually want a real answer, it gives the other person something concrete to respond to, and it takes the conversation somewhere neither of you expected.
The one habit: go first
Here’s where most people get stuck. They want depth but wait for the other person to initiate it. Both people are waiting. Nobody goes first. The conversation stays at cruising altitude.
The fix is embarrassingly simple: answer your own question first.
Don’t just ask “what’s been on your mind?” Say: “I’ve been thinking a lot about whether I’m actually happy or just comfortable. What about you — what’s been on your mind?”
When you share something real before asking, you create safety. You’re showing the other person the depth you’re inviting. They don’t have to guess what level of honesty is appropriate — you’ve shown them.
This is exactly why Ohh makes you answer first. You pick a question, write your answer, then send it. Your friend sees your honesty before they respond. That simple mechanic transforms a question into a conversation.
Five techniques that don’t feel forced
1. The follow-up pivot
When someone gives a surface-level answer, don’t accept it. Gently follow up. Not “go deeper” but: “What do you mean by that?” or“How did that make you feel?” or simply “Really? Tell me more.”
Most people are one follow-up away from saying something real. They just need to know you’re interested enough to ask twice.
2. The honest redirect
When the conversation is stuck on logistics — schedules, updates, plans — redirect with honesty: “Can I tell you something random? I’ve been thinking about…”
The “can I tell you something” opener works because it signals a shift in register. The other person leans in.
3. Use a prompt
There’s no shame in using a question from somewhere else. A conversation card. A list. An app. Saying “I saw this question and it made me think of you” is one of the most natural conversation openers there is.
4. Text first, talk later
Some of the deepest conversations start over text. A thoughtful question sent at night gives someone time to sit with it. They respond when the honesty kicks in — often hours later, often with something they’d never say face to face.
5. Don’t fill the silence
When someone pauses after a real question, let them pause. The silence is where the thinking happens. If you rush to fill it, you rob them of the space to go deeper.
The shortcut: If starting a deep conversation feels awkward, let Ohh do the heavy lifting. Pick a question from any deck, answer it, send it. The app handles the structure. You just show up honest. 3,000+ questions across 58 decks — there’s always one that fits the moment.
It gets easier
The first time you ask a real question, it might feel weird. By the third time, it feels normal. By the tenth, your friends start doing it back. Depth becomes the baseline, not the exception.
You don’t need to overhaul every relationship overnight. Start with one friend. One question. One honest answer. The rest follows.
Tonight, skip the “how are you.” Ask something that matters. Answer it yourself first. And see where the conversation goes when someone finally breaks the surface.