Texting is basically a high-stakes game of ping-pong where someone eventually forgets to hit the ball back. We’ve all been there. You're staring at a blinking cursor, wondering if "How was your day?" is too boring or if asking about their childhood trauma is a bit much for a Tuesday afternoon. Finding the right questions to ask over text isn't just about avoiding the "k" reply; it's about building a digital bridge that doesn't collapse under the weight of small talk.
Most people fail at texting because they treat it like an interview. It’s not. It’s a vibe.
Psychologists like Arthur Aron, famous for the "36 Questions That Lead to Love," suggest that gradual self-disclosure is the secret sauce for intimacy. But you can't just drop "What is your most terrible memory?" into a casual chat about Netflix. You need levels. You need a strategy that moves from low-stakes banter to high-stakes connection without triggering someone's fight-or-flight response.
Why Your Current Texting Strategy Probably Sucks
The biggest mistake? Boredom. If you ask a closed-ended question, you get a closed-ended answer.
"Did you have a good weekend?"
"Yeah."
End of scene. Roll credits. Instead, you need questions that demand more than a one-word confirmation of existence. According to research from Harvard University, people actually love talking about themselves—it triggers the same pleasure centers in the brain as food or money. If you aren't tapping into that, you're leaving engagement on the table.
The Low-Stakes Openers
Sometimes you just need to break the ice without looking like you’re trying too hard.
- "What's the most chaotic thing that happened in your office today?"
- "I need a tie-breaker: is a hot dog a sandwich or its own thing?"
- "If you had to delete every app on your phone except three, what’s staying?"
These work because they’re easy. They don't require deep soul-searching. They just require an opinion. People have very strong opinions about hot dogs. Use that.
Going Deeper: Questions to Ask Over Text for Real Connection
Once you've moved past the "How's work?" phase, you need to pivot. This is where most people get stuck. They stay in the shallows for three weeks until the conversation eventually dies of thirst. To move things forward, you have to be willing to be a little bit more specific.
"What’s a hobby you’ve always wanted to start but are way too intimidated to try?" This is a great question. It’s better than "What are your hobbies?" because it looks at the future and acknowledges vulnerability. Maybe they want to try Brazilian Jiu-Jitsu but are afraid of getting choked out by a stranger. Maybe they want to bake bread but hate flour. It tells you about their aspirations and their fears in one go.
The Power of "Wait, Tell Me More About That"
Technically, that’s a statement, not a question. But in the world of texting, it’s the most powerful tool you have. It shows you’re actually listening—or reading, anyway.
If they mention they had a weird dream, don't just say "lol crazy." Ask, "What was the specific moment in the dream where you realized things were getting weird?" Details matter. The more specific the question, the more invested the other person feels.
Navigating the "Talking" Phase
When you’re in that nebulous "talking" phase with someone you might actually like, the pressure to be interesting is immense. You want to be funny. You want to be deep. You mostly just don't want to be ghosted.
The trick is to ask questions that reveal character through hypothetical situations.
- "If we were trapped in a grocery store during a zombie apocalypse, which aisle are we claiming as our base?"
- "What’s the one song you’d be genuinely embarrassed to play on a first date?"
- "If you won a trip to anywhere tomorrow, but you had to leave in two hours, where are we going?"
Notice the use of "we" in some of these. It’s a subtle way to build a shared narrative. It’s playful. It’s not a marriage proposal; it’s a grocery store zombie scenario. Relax.
The Danger Zones: When Questions Go Wrong
Honestly, some questions are just text-killers.
Avoid anything that feels like a chore to answer. "Tell me your life story" is a terrible text. It’s too much work. Nobody wants to type out their autobiography on a glass screen while they’re waiting for the bus.
Also, watch out for the "rapid-fire" trap. If you send four questions in a row without acknowledging their answers, you aren't having a conversation. You're conducting a deposition. Stop it. Give the chat room to breathe.
Professional Networking via Text (Yes, It's a Thing Now)
In 2026, the line between LinkedIn and iMessage is thinner than ever. If you're texting a mentor or a colleague, the questions to ask over text shift significantly. You want to be respectful of their time but also human.
"Hey [Name], I was thinking about that point you made in the meeting. What’s the one thing you wish you’d known before you started this project?"
It’s professional, it’s targeted, and it’s easy to answer. It shows you value their expertise without being a sycophant.
The Follow-Up Game
If you met someone at a conference, don't just say "Nice meeting you."
Ask: "You mentioned you were reading [Book Name]—is it actually worth the hype or just good marketing?"
This gives them a chance to be an expert. People love being experts.
Dealing with the "Dry Texter"
We all know one. The person who responds with "lol," "cool," or "nice." It’s exhausting.
If you’re dealing with a dry texter, you have two choices: call it out or change the game. A bold move? Ask a question that forces a long-form thought.
"Okay, let's settle this: if you had to pick a theme song for your life right now, what would it be and why does it involve so much cowbell?"
If they still reply with "idk," it might be time to take the hint. Some people are just bad at texting, but others are just not that into it. Use your best judgment. Don't be the person shouting into a void.
Actionable Insights for Better Digital Chat
Texting isn't a science, but it is a skill. You get better by doing it, by failing, and by paying attention to what actually gets a response.
- Mirror the energy. If they send three paragraphs, don't reply with "k." If they send three words, don't send a dissertation.
- Use the "Visual Prompt." Instead of just text, send a photo of something weird you saw and ask, "On a scale of 1-10, how much do we regret this person's design choices?" It’s an instant conversation starter.
- Stop overthinking. Seriously. If you think a question is funny, send it. The worst that happens is they don't laugh. You'll survive.
- The "Would You Rather" pivot. When the conversation lulls, a classic "Would you rather always have to skip everywhere you go or always have to talk like a pirate?" can revive a dying chat in seconds.
Moving From Text to Reality
The ultimate goal of most texting is to eventually stop texting and actually see the person. Use questions to bridge that gap.
"I just saw [Restaurant/Park/Event] and thought of you. Have you actually been there or are we both missing out?"
This is the "soft close." It’s a question that leads directly to a plan. It’s low pressure because if they haven't been, the logical next step is to go together.
Next Steps for Your Messaging Mastery
Stop scrolling through your old chats and analyzing where it went wrong. Start fresh. Pick one of the "low-stakes" questions mentioned above and send it to someone you haven't talked to in a while. Don't over-explain why you're texting. Just send the question.
✨ Don't miss: Wisconsin drivers license renewal: What people usually get wrong about the DMV
Watch how the dynamic changes when you stop asking "What's up?" and start asking things that actually matter. The best way to get interesting answers is to be the person who asks interesting questions.
Start small. Be specific. And for the love of everything, stop using "How's it going?" as your primary opener. You're better than that.