44 questions to ask any friend to deepen your connection

Relationships

Jul 24

Written By Calm Editorial Team

Clinically reviewed by Dr. Chris Mosunic, PhD, RD, MBA

Looking for ways to get closer to your friends? These 44 questions can help you skip the small talk, deepen your trust, and get to know each other even better.

Adult friendships can be incredibly fulfilling, but they can be complicated, too. Between shifting schedules, career demands, and family obligations, even the closest connections can start to feel like a string of rescheduled plans and sporadic check-in texts. The love is there, the intent is real, but the depth is tough to maintain.

If you’re craving more meaningful moments with the people you care about—whether in-person or through your device—we get it. Sometimes, all it takes is a single thoughtful question to change the tone of a conversation. You don’t need a weekend getaway or hours of uninterrupted time. Just a willingness to go a little deeper, one thought at a time.

We’ve gathered easy-to-ask, intentional questions designed to help you build stronger, more honest friendships. This list works whether you're catching up over coffee, texting late at night, or squeezing in a few minutes between meetings. Let’s dive in.

What to consider before asking a friend personal questions

If you’re not used to opening up to a certain friend, it can feel weird at first. Maybe you want to tell them about a struggle you’re facing but are nervous you’ll be judged or misunderstood. Or maybe you want to know more about their life but worry they’ll think you’re being nosy.

These are all valid concerns because, let’s face it, relationships can be complicated. And while asking meaningful questions is a great way to build a connection, timing, tone, and mutual trust matter too.

Before diving in, take a moment to check the temperature of your relationship. Are you in a space where deeper conversation feels welcome? Are you both emotionally available right now, or is one of you maxed out from the day? A great conversation helps both people feel seen and safe.

Here are a few things to keep in mind:

Start small: You can ease in with lighter or more playful questions before exploring more personal ones. Think of it as dipping your toes in rather than cannonballing into emotional waters.
Be mindful of the moment: Dinner in a crowded space or sitting in a movie as the previews begin might not be the best time to ask, “Have I ever made you feel unseen?” Save deeper questions for when there’s room to reflect.
Focus on connection, not performance: There’s no right answer to these questions. They’re simply about creating a moment where something real can unfold between you.
Be ready to listen: Asking a good question is important, but holding space for the answer—without interrupting, deflecting, or making it about you—matters even more.

💙 Check out our Relationship with Others series for more on how to cultivate solid friendships.

44 questions to ask a friend to get closer

Meaningful questions don’t have to be complicated or intense. Sometimes, the simplest prompts open the door to conversations that linger (in a good way). Below, you’ll find a selection of thoughtful questions you can ask depending on your friendship or situation.

Whether you’re curled up on the couch, out for a walk, or chatting on the phone across time zones, these prompts can help you bridge the space between small talk and something deeper.

💙 Learn more about how to deepen your relationships by exploring the Meaningful Practice for Meaningful Friendship series.

Deepen the bond with your BFF

Even your closest friendships need care. These questions are great for checking in, celebrating each other’s growth, and remembering why this relationship matters:

What’s something you’ve learned about yourself this year?
When do you feel most like yourself?
Is there a time you’ve felt really seen or supported by me?
What’s something you’re carrying right now that no one really sees?
How do you know when you’re not okay, and what helps you find your way back?
What is most important to you in our friendship?
What do you miss about yourself that you’re working on reclaiming?
When was the last time you felt completely at peace?
What’s something you’re excited about right now?
Is there anything you wish we did more or less of?
What’s something we’ve been through together that you think has shaped us?

Get to know a new friend better

When you’re building a new friendship, the goal is to create space for it to develop naturally. These questions are casual, curious, and perfect for sparking connection without pressure.

What’s your favorite way to spend a weekend?
If you could teleport anywhere, where would you go and why?
What’s something most people don’t know about you but you wish they did?
What topics do you love diving into with people?
When do you feel most like yourself?
What’s something in your life that you’re looking forward to?
What’s a habit or ritual that’s grounding for you?
What’s a memory that always makes you smile?
What’s a simple pleasure that brings you real joy?
What makes you feel really supported by a friend?
What’s a dream you’re nurturing?

Good questions for a group of friends

These prompts work well for dinners, game nights, road trips — any moment when you want to go a little deeper than “How’s work?” but keep things light enough for everyone to join in.

If you could relive one day from the past year, what would it be?
What’s a food, smell, or song that instantly takes you back to childhood?
What’s something you’ve changed your mind about in the last few years?
What’s a piece of media that felt like it really got you?
What’s a memory from this friend group that’s stuck with you?
What’s a weird talent or skill you have that not many people know about?
What’s something surprising or unexpected you’ve learned recently?
Not including obvious stuff like your job or zodiac sign, what are three words that describe you?
What’s a moment you felt proud of this year?
If this group had a theme song, what would it be?
Who’s someone—famous or not—you admire, and what draws you to them?

Questions for when things feel stuck or distant

Friendships ebb and flow, and sometimes, you just need a gentle way to reconnect. These questions aren’t about fixing or confronting. They’re just about re-opening the lines of connection with care and clarity.

Is there anything you’ve been sitting with but haven’t felt ready to say?
Have you been feeling some distance between us lately?
Have I done something that felt off or hurtful, even unintentionally?
What do you need more of from the people in your life right now?
What does meaningful friendship look like for you lately?
What would make this friendship feel easier or better to you?
Is there anything lingering between us that we haven’t really talked about?
What do you wish this friendship had more room for?
Have you been feeling more like yourself lately or less?
What does emotional safety look like for you in a friendship?
How do you prefer to reconnect when things have gone quiet?

Questions to ask a friend FAQs

What are funny questions to ask your BFF?

Humor can be a shortcut to closeness, especially when you already share a foundation of trust. Funny questions work best when they’re playful and unexpected, like, “If you had to be a TV character for a week, who would you choose?” or “What’s the weirdest job you’ve ever had?” They help both of you loosen up and tap into joy, which can deepen your connection.

You don’t need to force laughs. A good, funny question feels like an invitation to be silly.

How do I ask deeper questions without making it awkward?

Start by being honest about your intention. You might say something like, “Hey, I’ve been thinking about this lately — curious what you think?” or “Mind if I ask you something a little more personal?” Framing it as curiosity rather than confrontation gives your friend a chance to opt in or redirect, which helps build emotional safety.

Also, pick your moment. A quiet walk, a long drive, or even texting late at night can create just the right atmosphere for more meaningful conversation.

What are fun questions to ask new friends?

When you’re getting to know someone, fun questions that invite storytelling are a great way to go. Try things like, “What’s a random talent you have?” or “What was your dream job as a kid?” These kinds of prompts create room for personality and light-hearted vulnerability without digging too deep too fast.

One good question, asked with warmth, can lead to a conversation that helps you both feel more connected and relaxed.

Why do questions help deepen friendships?

Thoughtful questions create a pause in the usual rhythms of conversation. When we ask and answer deeper questions, we’re letting someone into our inner world. That act of opening up, especially when it’s mutual, builds trust, emotional intimacy, and a sense of shared understanding.

It’s not just about the answers, either. Feeling heard in a moment of reflection can strengthen the foundation of a friendship more than any amount of small talk ever could.

Can I use these questions in group settings or with my family?

Absolutely. Many of these questions are versatile enough to use with a group of friends, a partner, or even around the dinner table with family. You might be surprised how much people are willing to share when given the right prompt in a safe, open environment.

If you’re in a group, try framing a question as a round-robin or giving people the option to “pass” without pressure. That way, you create a space that feels playful and inviting rather than stressful.

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questions to ask a friend

Calm Editorial Team