30 Questions to Engage Someone Beyond ‘How Are You?’

Table of ContentsView AllTable of Contents30 Questions to AskWhy Meaningful Conversations Are So ImportantKey Ingredients For Connecting With Others

Table of ContentsView All

View All

Table of Contents

30 Questions to Ask

Why Meaningful Conversations Are So Important

Key Ingredients For Connecting With Others

Our default question when we bump into someone—whether new acquaintance, old friend, or steadfast partner—is to say, “How are you?” It’s a perfectly reasonable thing to ask and considered polite protocol, but it’s not exactly the best way to engage someone on a deeper level. Not just because it’s a boring, expected question, but because it comes with aboring, expected answer: “I’m good.”

“We [often] resort tosmall talkbecause it’s socially safe, helps maintain norms, and avoids the vulnerability or discomfort that deeper conversations may bring,” saysCharles Sweet, PsyD, a psychiatrist and advisor at Linear Health.

So how do we break out of this cycle? And why is doing so important, anyway? We’ve got answers ahead, along with a list of questions you can whip out the next time you’re down to connect in a meaningful way.

Rachel Marmor, LMHCIt’s not about oversharing, but about offering glimpses of our true selves, which encourages others to lower their defenses and share what’s real for them.

Rachel Marmor, LMHC

It’s not about oversharing, but about offering glimpses of our true selves, which encourages others to lower their defenses and share what’s real for them.

50 Deep Questions to Ask Your Friends for Juicy Conversations

30 Questions to Ask Instead of “How Are You?”

How are you, how are you doing, how’s it going. All these are iterations of the same question and apt to elicit the exact same response across the board. Instead of choosing an expected question like this when catching up with a friend or meeting someone new, swap in a more open-ended question. The result? You might just find yourself making new friends and strengthening relationships.

Someone You’ve Just Met

Questions to Ask When You’re Forced to Talk to People

Someone You Already Know

Someone You’ve Known a Long Time

How to Deal When You’re Talking to a Conversational Narcissist

Meaningful conversations help usbuild intimacy, trust, and emotional validation.

“By opening up about our own thoughts, feelings, and experiences, we create a bridge that invites the other person to do the same,” explainsRachel Marmor, LMHC, a licensed mental health counselor based in South Florida. “It’s not about oversharing, but about offering glimpses of our true selves, which encourages others to lower their defenses and share what’s real for them.”

Even though it can be tricky to initiate these conversations orget vulnerablewith others at first, research tells us that doing so can come with some pretty awesome rewards, like experiencing greater happiness and feeling closer to others.A 2018 study also found that being more connected with others comes with a slew of benefits, including improvedself-esteem, better life satisfaction, and a sense of belonging.

She adds that these deeper conversations provide opportunities to gain new perspectives, offering insights into different life experiences, values, and ideas.

It’s one thing to have a list of questions to ask someone besides “how are you.” It’s another to take that conversational stepping stone and truly connect with other people. Here are the three key ingredients you need.

Saba Harouni Lurie, LMFTWhen we take the first step and are willing to share more about how we are actually feeling and what’s really on our minds, we allow the person we are speaking with to do the same.

Saba Harouni Lurie, LMFT

When we take the first step and are willing to share more about how we are actually feeling and what’s really on our minds, we allow the person we are speaking with to do the same.

Build Trust

Sharing about ourselves first is an effective way to naturally deepen relationships, built trust, and move us beyond superficial niceties.

“When we take the first step and are willing to share more about how we are actually feeling and what’s really on our minds, we allow the person we are speaking with to do the same,” notes Lurie. “It’s a way to signal that we want to have a more honest and in-depth conversation and can serve as an invitation for the other person to do the same.”

Actively Listen

All meaningful conversations require a good balance of listening and sharing. Nobody wants to hang with someone who talksatthem or doesn’t really seem to care about what’s being discussed.

“Active listeningis the cornerstone of meaningful engagement,” Marmor says. “It requires us to be fully present, setting aside distractions and tuning in not just to the words, but to the emotions, the pauses, and the unspoken messages.” This is where the magic of true connection happens—when both people feel understood and valued.

Have Genuine Curiosity

It’s one thing to listen and respond, but being sincerely curious about the other person is going to create an innate sense of trust and connectedness, saysKimberly Best, RN,a dispute resolution expert at Best Conflict Solutions.

Rachel Marmor, LMHCPeople open up when they feel safe, when they know their thoughts and feelings will be met with kindness and without judgment.

People open up when they feel safe, when they know their thoughts and feelings will be met with kindness and without judgment.

Create a Safe Space

Finally, creating a safe and supportive environment is essential. “People open up when they feel safe, when they know their thoughts and feelings will be met with kindness and without judgment,” Marmor says. “In this space, even silence can be powerful. Reflective pauses allow for thought, for the conversation to breathe, and for both people to connect in a way that words alone cannot achieve.”

Do all these things and you’ll find yourself in a place where real connection lives and where relationships go deeper and feel more satisfying.

2 SourcesVerywell Mind uses only high-quality sources, including peer-reviewed studies, to support the facts within our articles. Read oureditorial processto learn more about how we fact-check and keep our content accurate, reliable, and trustworthy.Kardas, M., Kumar, A., & Epley, N. (2022).Overly Shallow?: Miscalibrated Expectations Create a Barrier to Deeper Conversation.Journal of Personality and Social Psychology, 122(3), 367–398.https://doi.org/10.1037/pspa0000281Amati V, Meggiolaro S, Rivellini G, Zaccarin S.Social relations and life satisfaction: the role of friends.Genus. 2018;74(1):7. doi:10.1186/s41118-018-0032-z

2 Sources

Verywell Mind uses only high-quality sources, including peer-reviewed studies, to support the facts within our articles. Read oureditorial processto learn more about how we fact-check and keep our content accurate, reliable, and trustworthy.Kardas, M., Kumar, A., & Epley, N. (2022).Overly Shallow?: Miscalibrated Expectations Create a Barrier to Deeper Conversation.Journal of Personality and Social Psychology, 122(3), 367–398.https://doi.org/10.1037/pspa0000281Amati V, Meggiolaro S, Rivellini G, Zaccarin S.Social relations and life satisfaction: the role of friends.Genus. 2018;74(1):7. doi:10.1186/s41118-018-0032-z

Kardas, M., Kumar, A., & Epley, N. (2022).Overly Shallow?: Miscalibrated Expectations Create a Barrier to Deeper Conversation.Journal of Personality and Social Psychology, 122(3), 367–398.https://doi.org/10.1037/pspa0000281Amati V, Meggiolaro S, Rivellini G, Zaccarin S.Social relations and life satisfaction: the role of friends.Genus. 2018;74(1):7. doi:10.1186/s41118-018-0032-z

Amati V, Meggiolaro S, Rivellini G, Zaccarin S.Social relations and life satisfaction: the role of friends.Genus. 2018;74(1):7. doi:10.1186/s41118-018-0032-z

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Rachel Marmor, LMHC#

30 Questions to Ask Instead of “How Are You?”#

Someone You’ve Just Met#

Someone You Already Know#

Someone You’ve Known a Long Time#

Saba Harouni Lurie, LMFT#

Build Trust#

Actively Listen#

Have Genuine Curiosity#

Create a Safe Space#