The right questions to get to know someone are not a checklist, they are a door-opener, and what you do after you ask matters just as much as the question itself. That is the view of Karen Vincent, LCSW, therapist and clinical director at Octave, who argues that a well-chosen question can ‘snap someone out of autopilot and make them reflect and want to connect.’
The problem with tired openers like ‘So, tell me about yourself’ is their size. Too broad, too vague, too easy to blank on. Sharper, more specific questions give the other person something real to grab onto, and give the conversation somewhere to actually go.
Listen First, Ask Second: The Real Point of Good Questions to Get to Know Someone
Vincent is clear that the follow-through is everything. Rather than moving straight to your next question after someone answers, she recommends tracking whatever seems to light the other person up and following it. ‘The first question cracks open the door, but the follow-up questions are where you get the real connection,’ she says.
Her example: if someone says their dream trip is two weeks in Japan, ask why Japan. Ask what they would do there. Ask whether they have always wanted to go. That chain is a conversation, not an interrogation, and the distinction matters.
Equally important is reading the room. If someone is sharing freely and leaning in, you can go deeper. If they give a short answer or change the subject, take the hint. Vincent notes that someone might open up happily about one area of their life while becoming noticeably quieter around another, and pushing through that signal works against connection, not for it.
The Categories That Cover the Most Ground
The range of useful questions to get to know someone runs from deliberately light to fairly personal, and the order in which you deploy them should follow the energy of the conversation rather than any fixed sequence. A few broad territories worth covering:
General likes and dislikes are the natural starting point, favourite foods, music taste, go-to karaoke song, preferred holiday style. These are low-stakes, easy to answer, and often reveal more than they appear to. Vincent recommends starting with casual topics and letting the other person’s answers guide where things go next.
Questions about growing up sit in the middle ground. Childhood memories, old obsessions, embarrassing phases, these tend to be warm rather than heavy, though some corners of a person’s past are more sensitive than others. Pay attention to the shift in tone when it comes.
Family, friendships, and relationships get more personal still. The people someone keeps close say a lot about what they value, and questions about how they met their best friend or who they call first when something big happens can tell you a great deal about how they show up in relationships.
Values and beliefs (including views on politics, spirituality, or causes they care about) can feel daunting early on, but they are also where you find out fastest whether you are genuinely compatible with someone. The key, as Vincent implies, is to make it a conversation rather than a cross-examination. If you are asking, be ready to answer.
Career questions are useful when kept conversational. What motivated their choices, what they find fulfilling, what they would do if money were no object, these land very differently from ‘where do you see yourself in five years?’
Finally, everyday habits and routines (morning person or night owl, homebody or always out) give you a realistic picture of what being part of someone’s daily life might actually look like. Compatibility on the big stuff matters, but so does whether your idea of a good Saturday is remotely similar.
The questions themselves can be found across categories on platforms built for connection, from conversation-starter apps to therapy-adjacent tools, Spotify and Apple Music both feature playlist-based features that surface exactly the kind of taste-based questions (‘what song really affects your mood?’) that Vincent’s framework supports as strong openers.
Pick the category that fits where you are with someone, start lighter than you think you need to, and let the answers do the steering from there.