Asking Better Questions Than 'How Was Your Day?'

“How was your day?” is the most common question on dating apps and also the least useful. It’s easy to ask, which is its appeal, and impossible to answer well, which is its problem. “Good, you?” is the only reasonable response, and now both people are back to square one. It’s the conversational equivalent of wallpaper — you could paste it into a thousand chats and nobody would notice.

The solution isn’t to ask deep, probing questions to a stranger. It’s to ask slightly better ones.

Why question quality matters

Huang and colleagues studied speed-dating interactions and found that people who asked more follow-up questions were rated as significantly more likable by their partners [1]. The key word is follow-up: not just more questions, but questions that responded to what the other person actually said. This signaled genuine interest.

Aron and colleagues’ famous “36 questions” study demonstrated that reciprocal self-disclosure — sharing progressively personal information — builds closeness even between strangers [2]. You don’t need to use their exact questions on a dating app, but the principle holds: people feel closer to someone who asks them things worth answering.

The problem with generic questions

Generic questions fail because they have generic answers.

Question	Typical answer	Problem
“How was your day?”	“Good, you?”	Nothing to work with.
“What do you do?”	“[Job title]”	Facts, not personality.
“Where are you from?”	“[City name]”	Same.
“What do you do for fun?”	“Hang out with friends, watch TV”	So broad it’s meaningless.
“Tell me about yourself”	“I don’t know, what do you want to know?”	Too open-ended.

These questions aren’t wrong. They’re just low-yield. They produce exchanges that feel like a form rather than a conversation.

Better questions by category

Instead of “how was your day?”

• “What was the highlight of your week?” — Forces them to pick something specific.
• “What are you most looking forward to this weekend?” — Future-focused and easier to answer.
• “Did anything funny happen to you today?” — Invites a story.

Instead of “what do you do for fun?”

• “What’s the last thing you got really into?” — Could be a show, a hobby, a recipe, a rabbit hole.
• “What would you do with a surprise day off?” — Reveals priorities and personality.
• “Are you the kind of person who plans their weekend or wings it?” — Personality question disguised as a preference question.

Instead of “where are you from?”

• “What’s your neighborhood like?” — More revealing and more interesting.
• “What’s the best place you’ve lived?” — Invites a story.
• “Do you feel like a local or are you still figuring this place out?” — Conversational, personal.

Instead of “what do you do?”

• “Do you like what you do, or is it just the thing that pays the bills?” — Gets at how they feel about work, not what their title is.
• “If money didn’t matter, what would you spend your time doing?” — Hypothetical but revealing.

The follow-up principle

The best conversational tool on a dating app isn’t a great opening question — it’s a great follow-up. When someone tells you something, dig into it rather than moving to the next topic.

Surface conversation:

“What did you do this weekend?” “Went hiking.” “Nice. I like hiking too.”

Deeper conversation:

“What did you do this weekend?” “Went hiking.” “Where’d you go? I’ve been looking for new trails.” “This place called Eagle Creek — it’s got a waterfall about three miles in.” “That sounds amazing. Are you more of a serious hiker or a ‘this is basically a walk with trees’ person?”

The second version goes somewhere. The first version dead-ends.

A fictional example

Jess and Alex matched on Hinge three days ago. Their conversation has been pleasant but flat — a series of exchanged facts about jobs, hometowns, and generic weekend plans. Jess decides to try a different approach.

Instead of asking “how was your Monday?” she sends: “OK, important question — what’s your go-to comfort meal when you’ve had a terrible day?”

Alex replies: “Easy. My grandmother’s chicken soup recipe. I make it every time something goes wrong. It’s like medicine.”

Now they’re talking about grandmothers, family traditions, cooking, and comfort — all from one specific question. Jess didn’t ask anything deep or invasive. She asked something specific enough to get a real answer.

Questions to avoid

Anything that feels like an interview. “What are your five-year goals?” “What are you looking for in a partner?” “What are your biggest strengths and weaknesses?” Save these for later, if ever.

Anything too personal too soon. “Why did your last relationship end?” “What’s your biggest fear?” These require trust that hasn’t been built yet.

Anything with a right answer. “Do you like dogs?” (Who says no to this?) “Do you think communication is important?” (Obviously.) These feel like tests, not questions.

Rapid-fire questions. Sending three questions in one message turns a conversation into a quiz. Ask one, let them answer, then follow up.

Good questions aren’t clever — they’re specific. You don’t need to be witty or philosophical. You need to ask something that has an answer worth giving. “What’s the last thing you cooked?” is more interesting than “what’s the meaning of life?” because one of them will produce a real story and the other will produce an awkward deflection.

For how to start the conversation in the first place, see how to start a conversation from their profile.