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You’re in the talking stage, and you’ve already covered work, weather and what they watched last night. The short answer: pick starters that are easy to answer and a little personal, then follow up on whatever they say. Swap one answer for one of yours so it never feels like an interview. Keep the tone light, and save the heavier stuff for when you both clearly want it.
Use these in person, on a call, or on the walk between the two.
Every question here comes from Lolo Cards - 4,700 conversation cards for iPhone.
Why the talking stage stalls
The talking stage can stall when the conversation stays on the surface: how was your day, what are you up to, anything fun this weekend. Nobody is bored, but nobody learns much either.
The fix is smaller than you think. A question that gives them room to say something only they would say is plenty. Your crush questions are built for that, and the easy ones work just as well when you’re not sure what to call this yet.
Starters that show who they are
Start with things that are fun to answer and hard to answer with one word. These work over coffee, over a late call, or as a text that you finish out loud later.
- What’s a hobby of yours I should know more about?
- What’s something you’re passionate about that doesn’t come up much in conversation?
- What’s your favorite way to unwind after a long week?
These give them room to talk about what matters to them. Then ask one more thing about it.
Keep it light: dating stories and silly ones
The talking stage is allowed to be funny. Dating stories are an easy way to laugh together and learn what someone finds attractive, awkward or ridiculous without turning the conversation serious.
- What’s the worst pickup line anyone’s ever used on you?
- What’s the most memorable first date you’ve ever been on?
- What’s a green flag that instantly makes you interested in someone?
Mimi’s rule: tease the situation, never the person. If they tell you about a disastrous date, laugh with them, not at their ex. And answer your own question after they answer theirs.
How not to sound like a job interview
Question, short answer, next question. If that’s the rhythm, you’re running an interview, and they can feel it.
Two habits fix it:
- Follow up before you move on. Researchers who studied question-asking in conversations between strangers found that “follow-up questions are particularly likely to increase liking” because they signal that you were listening. The same research warned that “rude or too repetitive” questions could hurt, so one thoughtful follow-up is enough.
- Trade answers. Ask, listen, then share your own. A question that only goes one way starts to feel like a quiz.
If you’re on a call, it helps to pick the question before you dial. A call can go quiet fast when it starts with twenty seconds of “so… what should we talk about?”
When you’re ready to go a bit deeper
You can tell when the talk is warming up: longer answers, tangents, a laugh that arrives before you finish the sentence. That’s a good moment to ask something with a bit more weight.
You might worry it’ll turn awkward. A set of experiments with pairs of strangers found the opposite: people expected deeper conversations to feel awkward, and they came out less awkward and more connecting than predicted. Participants also underestimated how much their partner wanted to go beyond small talk.
- What’s something you wish people asked you about more?
- What’s something about you that surprises people once they get to know you?
- What’s a place you grew up that shaped who you are?
The talking stage is also a fair time to ask where things are heading, in a way that’s easy to answer.
- What’s your honest take on the “situationship” phase of modern dating?
- What’s something you think we should do together that we haven’t yet?
Read the room. If an answer gets short, go back to something light.
A simple plan for your next conversation
- Open with one easy starter from the first list.
- Follow up on whatever they say once.
- Share your own answer.
- Try one funny question when things get stiff.
- If you’re both leaning in, move to a deeper one.
Want more to choose from? The full list of questions to ask your crush is there when you need it, and if you’re heading toward an actual date, see what to talk about on a first date.
