Questions that help you spot red flags early
Warm, practical questions that help you notice how someone handles disagreement, speaks about past partners and responds to a small boundary.
20 starters to use
1.What's been the best part of your week so far?
A warm opening that lets you hear what they notice and value, without putting anyone on the spot.
2.How do you usually spend a free Saturday?
Ordinary details make it easier to see how they talk about their life and whether they ask about yours.
3.When you disagree with someone close to you, how do you tend to handle it?
It invites them to describe their approach to conflict rather than defend themselves.
4.What does a good apology look like to you?
It opens a calm conversation about accountability without accusing anyone.
5.How do you like someone to tell you when you have got something wrong?
It asks about feedback and repair in a way that feels practical rather than harsh.
6.What's something small someone did recently that you appreciated?
It shows whether they notice kindness and can speak generously about other people.
7.How do you usually talk about people you have dated before?
It gives a sense of whether they speak with care or only in blame.
8.When a plan changes at the last minute, what's your usual reaction?
It can reveal how they handle inconvenience and communicate under mild pressure.
9.What's a small boundary you are glad people respect?
It opens the topic of boundaries without making it personal or confrontational.
10.Is there anything you would rather not talk about yet?
It makes consent part of the conversation and gives them an easy way to say no.
11.What does respect look like in a friendship for you?
It lets them describe values in their own words rather than agree with a label.
12.How do you usually let someone know you are not interested?
It can show whether they value honesty and kindness when the answer is difficult.
13.What's a time you changed your mind about something important?
It invites humility and reflection without asking for a confession.
14.When you are busy or stressed, how do you like to communicate?
It helps you both talk about reliability before small misunderstandings build up.
15.What would make you feel comfortable about meeting for the first time?
It turns safety and comfort into a shared practical conversation.
16.How do you feel about a short first meeting in a public place?
It states a sensible shape for a first date and lets you hear their response.
17.I usually arrange my own transport for a first meeting, and I like to meet at the place. Does that work for you?
It sets a clear, ordinary boundary and gives them a chance to respond respectfully.
18.What's something you are looking forward to this month?
A light question that keeps warmth in the conversation and lets you see what they care about.
19.What's a question you wish people asked you more often?
It gives them room to steer the conversation and often produces a thoughtful answer.
20.How do you like to take things when you are getting to know someone?
It invites them to say what pace feels right and makes room for your pace too.
Why these work
These questions work because they invite someone to show you how they think, not just what they think of you. A question about disagreement can reveal whether they listen, explain or dismiss. A question about past partners can show whether they speak with care or contempt. A question about a small boundary can show whether they treat your comfort as ordinary and worth respecting. You are not looking for a verdict after one message. You are gathering a sense of how they treat people when the conversation is still easy.
They work best when they sound like part of a normal conversation rather than a checklist. You are not looking for perfect answers. Notice whether the person is thoughtful, whether they ask you something back, and whether their words and tone match. Warmth, curiosity and a little humour often tell you more than a polished speech.
They also give you room to share your own standards without making an accusation. If you say what you value, you learn how someone responds to a difference of view. You can be kind and still notice when an answer leaves you uneasy.
How to use them without sounding scripted
Use one question at a time and let the conversation breathe. Answer it yourself first if that feels natural, so it becomes a swap rather than an interview. If you ask how someone handles disagreement, you might say how you like to cool down before talking things through. That makes the question easier to answer honestly and shows you are not setting a trap.
Ask follow-ups rather than stacking questions. A simple 'What did you do next?' or 'How did that feel?' often tells you more than a new topic. Notice whether they ask about your experience too. A conversation that only moves in one direction can be tiring, even when the answers are pleasant.
Keep the tone light and leave space for 'I would rather not say yet'. That answer is allowed. If someone gives a very short reply, you can let it go and see how they behave later. You do not need to collect every answer in one sitting. Early conversation is a chance to notice patterns, not to complete an assessment.
Trust the small moments. Did they remember something you said? Did they make room for your view? Did they respond well when you said you preferred to take things slowly? These are often more useful than a long answer about values.
What to avoid
Avoid turning the conversation into a test they do not know they are taking. Traps and trick questions tend to produce confusion, not clarity, and they can make a kind person guarded. Ask plainly, listen to the answer, and let ordinary behaviour do the rest.
Do not accuse someone of being dishonest because they have a past, or press for details about former partners. You can ask how they speak about people they used to know. You can notice whether the story is all blame and no reflection. You are allowed to decide that a pattern of excuses wears you down, and you do not need to argue them out of it.
Try not to label every awkward moment a red flag. Nerves, a flat joke or a slow reply can happen to anyone. Look for a repeated pattern over time, especially around respect, honesty and boundaries. If something feels off, you can slow down without making a speech.
Do not ignore a pattern of excuses just because the person is charming. Charm and reliability are different things. You can be warm and still keep your own standards.
Moving from talking to meeting
When you feel ready to meet, suggest something short and public. A busy café, a park, a market or a museum are all easy places to talk and easy places to leave. Meet there rather than arranging to be collected. Arrange your own way there and back, and tell a friend where you are going and when you expect to be finished.
Keep the first meeting brief enough that you both have an easy exit. You can always plan a second meeting if it goes well. Choose a time that suits you and a place where you feel comfortable. If you would rather meet in daylight, say so. If you would rather keep it to one hour, say that too.
Watch how they respond to small practical boundaries. A person who is respectful will usually be glad to know what works for you. If they push, sulk or try to make you feel odd for having a preference, that is useful information. You do not need to debate it.
You can leave whenever you want. You do not owe anyone an explanation beyond a simple goodbye. If you feel uneasy, trust that and make your way home. A first meeting is there to help you learn more, not to prove anything.
Questions people ask
How do I ask a question like this without sounding suspicious?
Introduce it as something you are curious about, then answer it yourself if that feels natural. Keep your tone warm and let them choose how much to share. One thoughtful question is usually better than a string of them.
What if someone avoids a question I ask?
Let it go once and see how they behave in the rest of the conversation. You can come back to it later if it matters, or decide that their unwillingness to engage tells you enough. You do not need an answer on the spot.
Is one odd answer enough to rule someone out?
Not usually. Look for a pattern over several conversations, especially around respect, honesty and boundaries. One awkward reply may be nerves; a repeated refusal to hear you is more useful information.
Should I meet someone if I feel uneasy, even if they seem charming?
You can slow down or not meet at all. Unease is worth listening to, and you do not have to justify it. If you do meet, choose a short public meeting, tell a friend and arrange your own way there and back.
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The situation, what works and what to avoid are 6on7's own editorial brief for this guide. The written guide is drafted with AI from these facts and checked automatically before it is published.