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28 Questions To Ask To Deepen Your Relationships

How well do you really know your spouse? Your best friend? Or your child?

Even if we spend a lot of time with someone, this doesn’t necessarily mean that we understand what makes them tick. If we’re pretty astute, we may think we know where our boyfriend may want to go on vacation, what sort of restaurant our best friend likes, or which movie our son is clambering to see. And maybe we do.

However, such information can still leave us out in the cold when it comes to knowing what makes that other person happy, afraid, angry, or motivated. Wouldn’t you like to be better acquainted with your loved one’s answers to such fundamental issues?

Also – bonus. Focusing on what’s going on with someone else and being a kind of detective as you learn more about them can temporarily get your mind off yourself – which can lower your stress level. Often our relationships suffer when we’re preoccupied with this or that worry.

Logically we realize that worry doesn’t do us much good, but it can still be difficult to get our minds off our troubles. Try listening closely to your partner as you learn more about them.

Often in a relationship of any kind, be it romantic, a friendship, or a colleague, there is one person who talks more than the other person. Taking turns asking some of the questions below can help to balance your relationship, strengthen your connections, and to show them that you really want to know more about them.

First, the somewhat milder or more innocuous questions:

  1. How do you recharge, rejuvenate, and replenish your energy?
  2. What was the best thing that happened to you today?
  3. If you could identify with one fictional character (from a book, show, or movie) who would it be?
  4. If your job gave you a surprise three-day paid break to rest and recuperate, what would you do with those three days?
  5. Who was your craziest or most interesting teacher?
  6. Where are some unusual places you’ve been?
  7. What tip/tips have you picked up from your job/jobs?
  8. What hobby would you pick up if time and money weren’t issues?
  9. Do you like things to be carefully planned or do you prefer to just go with the flow?
  10. What do you wish you knew more about?
  11. Who do you think has had the largest influence on the person you are today?
  12. What’s your favorite way to start the day?
  13. If all jobs had the same pay and hours, what job would you like to have?
  14. What are you looking forward to in the coming months?

With people you know (or think you know) better, you could also delve into the following areas:

  1. What happened today that made you keep on going?
  2. What’s one thing that’s happened to you that has made you a stronger person?
  3. What do you spend the most time thinking about?
  4. How do you judge a person?
  5. What personality trait do you value most and which one do you dislike the most?
  6. What do you need help with the most often?
  7. What problem are you currently grappling with?
  8. Which of your bad habits would be the hardest for you to give up?
  9. What would it take for you to be more ready to give up that habit?
  10. What positive habit do you have now that you wish you had started earlier?
  11. What prompted you to pick up that positive habit?
  12. When did something start out badly for you but in the end, turned out great?
  13. If you had one day left to live, what would you do first?
  14. What do you wish I knew about you that I haven’t asked?

If someone seems uncomfortable about answering any question, don’t push them to answer, of course. You could offer some of your own answers, without dominating the conversation. Take turns talking, with the listener not interrupting. This is actually a technique used in couples counseling, if one or both people feel unheard and experience the other person as more invested in their next retort than hearing the other person. Sometimes a timer for three or five minutes is even used – but clearly it’s not always necessary to be this “formal” about the process.

The idea is to give each person space to “take center stage” and feel accepted and seen, without being afraid that they’re going to be talked over or dismissed. The listener can make short empathic comments such as “How frustrating that must have been for you” or “They sound like an inspiring person” without moving the focus onto themselves.

Showing genuine curiosity and interest in someone else, with unconditional acceptance, is one of the most precious gifts you can give. Try it.

28 Questions To Ask To Deepen Your Relationships

Rachel Fintzy Woods, MA, LMFT

Rachel Fintzy Woods, M.A., LMFT is a licensed psychotherapist in Santa Monica, California. Rachel counsels in the areas of relationships, the mind/body connection, emotion regulation, stress management, mindfulness, emotional eating, compulsive behaviors, self-compassion, and effective self-care. Trained in both clinical psychology and theater arts, Rachel works with people to uncover and develop their unique creative gifts and find personal fulfillment. For 17 years, Rachel has also been conducting clinical research studies at University of California, Los Angeles (UCLA) in the areas of mind/body medicine and the interaction of psychological well-being, social support, traumatic injury, and substance use. You can read more about Rachel at her website:

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APA Reference
Fintzy Woods, R. (2018). 28 Questions To Ask To Deepen Your Relationships. Psych Central. Retrieved on May 30, 2020, from


Last updated: 18 Jan 2018
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