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

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 a boring, expected answer: “I’m good.”

“We [often] resort to small talk because it's socially safe, helps maintain norms, and avoids the vulnerability or discomfort that deeper conversations may bring,” says Charles 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.

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

1. What’s your connection to [this event/the host/this location]?
2. What do you think about the music/vibe here?
3. Did you come with anyone and who are you hoping to meet? (i.e. business contacts, new friends, etc.)
4. Have you been here before and what inspired you to attend?
5. How’d you find yourself here today?
6. What did you think about [specific part of the event, such as a speech, performance, or activity]?
7. What do you usually order/do here?
8. How’d you find out about this [place/event]?
9. Have you met anyone here that you thought was especially unique or interesting?
10. Any big plans for later in the day/tomorrow?

Someone You Already Know  

1. What’s been going on since the last time we met up?
2. Whatever happened with [XYZ thing they brought up last time]?
3. Have you experienced anything new that's impacted who you are lately?
4. Anything exciting going on in your life?
5. Have you learned or discovered anything cool lately?
6. What are you most excited about in life right now?
7. Have any new goals or plans you’re working on?
8. Read/watched anything good since we last met up?
9. How is [person important to them] doing?
10. What's a rose (good thing) and a thorn (bad thing) happening in your life right now?

Someone You’ve Known a Long Time 

1. What’s been on your mind and heart lately?
2. How are you really doing? Is there anything I can do to support you right now?
3. How have you been doing with [challenge/goal]?
4. How have you been spending your time and what have you been investing your energy into lately?
5. What are you looking forward to today/this week/this weekend?
6. How’s it going with [person important to them]?
7. Is there anything you’ve wanted to talk about with me lately?
8. What was your high and low today?
9. Any major life or work updates?
10. Is there anything you'd like to share you're proud of that I can celebrate with you?

Why Meaningful Conversations Are So Important

Meaningful conversations help us build 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,” explains Rachel 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 or get vulnerable with 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 improved self-esteem, better life satisfaction, and a sense of belonging.

"When we ask more personalized and specific questions, we can strengthen our connections by showing a genuine interest in getting to know each other," adds Saba Harouni Lurie, LMFT, founder of Take Root Therapy. "Personalized questions also encourage authentic communication, where both parties can express their true thoughts and feelings."

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

Key Ingredients For Connecting With Others

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. 

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 talks at them or doesn't really seem to care about what's being discussed.

“Active listening is 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, says Kimberly Best, RN, a dispute resolution expert at Best Conflict Solutions. 

“This is where conversations can really come alive,” she says. “When someone shares a detail about their life, follow up on it. If they mention a new hobby, ask what drew them to it. If they talk about a challenge they're facing, express interest in how they're approaching it. Be open to learning something new from each interaction.”

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.