30 Questions to Encourage Vulnerability in a Relationship, According to a Therapist

Envision this: You’re eager to get to know someone better, perhaps romantically or maybe platonically as a friend or even a member of your family. They spend time with you and while you always enjoy your time together, you can’t seem to have a deep, vulnerable conversation beyond superficial subjects. Whenever you try to, your attempts are deflected or, worse, it ends up with you sharing intimate insights that aren’t reciprocated.

There’s an art to vulnerable conversation, and you may need to approach it in a different way. Vulnerability is best approached as a reciprocal act—so be prepared to be just as vulnerable as the person you’re hoping will open up to you.

With this in mind, we're sharing these therapist-approved conversation starters—I’m a therapist myself and love supporting folks in building deeper relationships. Read on, try them out, and let the connections flow.

10 Questions for Vulnerable Conversations With Romantic Interests

We don't recommend getting too deep too quickly, so it's probably best not to break these out on a first date. Once things start moving forward with a potential long-term partner, however, these questions can help encourage them to open up, become more vulnerable, and share information that will help you get to know them better and may help you learn more about your compatibility.

1. Have you ever been in love before? This question is deep and intimate—consider asking it when you’ve already started to dip your toe into more personal conversations.
2. Do you know your love language? If so, what is it? If they don’t know their love language, you can consider taking our love language quiz together.
3. What is the most important relationship you’ve ever been in? This question is vague and open-ended by design, allowing them to share as much as they’d like. They might share about a romantic, platonic, or familial relationship.
4. When you think of the “perfect couple,” who comes to mind? There is no such thing as the perfect couple, but chatting about movie characters, parents, or family friends who embody true love can be a revealing conversation.
5. What do you value in a romantic relationship? It can be easy to simply ask, “What are you looking for in a relationship?” In turn, the answer may fall a bit flat. However, this question is an example of a specific ask that can lead to deeper vulnerability.
6. How do you define love? No two people will answer this the same.
7. What are your relationship dealbreakers? Not everyone wants to be monogamous, get married, or have children. Some aren’t open to the idea of stepchildren. This question can open the floor up for important information.
8. What are your relationship goals? Alternatively, some must get married, have children, or be monogamous. The more you learn, the more clarity you will have.
9. Who was your first crush and what drew you to them? This question can bring up sweet childhood memories and an invitation for deeper intimacy.
10. If you could change one decision you made in the past, what would it be? The answer may surprise you.

Remember, you'll likely have to answer these questions too, so be prepared to reciprocate when the other person opens up.

10 Questions to Invite a Friend to Open Up To You

You may have some ride-or-die friends since childhood, but sometimes we take those relationships for granted and may miss out on opportunities to connect on a deeper level. These questions will help you feel even closer to your best friends:

1. What’s your favorite friendship memory? Different things stand out to different people – learning about their favorite friendship memories can help you learn a lot about them.
2. Have you ever had a friendship fall out? If so, what happened? Friendship breakups can be very tender, so read the room when asking this question. But, they can also be full of insight and wisdom, leading this question to be a rich one.
3. What do you look for in a friend? This may sound overly simplistic, especially if you’re asking an established friend. But, this question is fantastic because it doesn’t leave any room for assumptions.
4. Who was the first friend you ever made? What do you remember about them? This question offers the opportunity to learn more about their childhood and upbringing, too.
5. What is the kindest thing a friend has ever done for you? Similar to the love languages question in the previous section, this offers an opportunity to learn what sort of care stands out to them.
6. What do you feel is the kindest thing you’ve ever done for a friend? This one is particularly vulnerable because it invites the person to identify what they perceive to be the kindest thing they’ve done for a friend, which can be very telling.
7. What do you look for in a friend group? Even if you two share the same friend group, the things that matter to them may be different from the things that matter to you.
8. How did you meet the last friend you met? Friendships can have the best meet-cute stories.
9. What did you think of me when we first met? First impressions can be revealing—even being asked this question is quite intimate.
10. How would you describe yourself as a friend? Inviting someone to reflect on their own qualities and attributes can lead to them opening up in no time.

10 Questions to Connect With New People in Your Life

You may want to hold off on getting too deep with new people right away. Once you're comfortable and have built some trust and rapport, when it feels like a good time to build a deeper connection with someone—whether it is a new friend or new romantic interest—these questions can help:

1. If you could have any job in the world, regardless of income or status, what would it be? This job opens up the gateway to discuss one’s hopes and aspirations.
2. What was the last dream you had? Dreams can be deep and symbolic or silly and meaningless – chatting through their most recent dream can leave the opportunity for them to share more about the innerworkings of their mind.
3. Tell me about your first day of high school and any message you wish you could go back in time to tell your younger self. Not everyone will remember their first day of high school vividly, but it does open up the conversation for what they were like in high school and how they’ve matured into adulthood.
4. What is the greatest challenge in your life right now? This question inevitably invites deep vulnerability. Make sure you’re in a space to emotionally receive such delicate information.
5. When was the last time you saw the sunrise? What were you doing? This is an innocent question that can be very disarming. Perhaps they had insomnia or maybe they were on an adventure in a foreign country. Either way, you’ll learn a lot about them as a person from their answers.
6. When was the last time you were really disappointed? Learning what disappoints someone can be illuminating. It could be as mundane as forgetting hot sauce when picking up their takeout order or not having someone very important to them show up for a major event.
7. What’s your greatest goal in life? This could be money, love, relationships, or career-related – it all depends on who you ask.
8. When you were younger, what type of person did you hope to grow up to be? They might describe the qualities they wanted, the glamor of a certain career, or a more easeful lifestyle.
9. When was the last time you told someone no? How did you feel? It is common to have a hard time saying no to others and can often be rooted in other adverse experiences. This is a conversation starter that can open up a larger conversation about relational challenges.
10. What do you think would make you deeply happy in your life? We all have ideas of what we think would complete us. Learning about theirs can create a bond quickly. 

Something to Keep in Mind

A 2022 study shows that vulnerable conversation about topics even as deep as loss can lead to increased closeness. However, there is a time and place for everything. Some relationships are a slow burn and it can take time for someone to open up. Respect their pace and don't force anything. Expecting vulnerable shares without a trusting relationship isn’t realistic and it is important to build trust and rapport before delving into more sensitive and personal topics.

Before asking one of the above questions, ensure it feels like a comfortable environment to do so. For example, you might not ask someone a deeply personal question in front of strangers or if it is your first time meeting because it could make them very uncomfortable and unwilling to open up in the future. Being mindful of how you use these questions is key to developing deeper, more vulnerable relationships.