How thought-provoking conversations help deepen relationships.

Thought-provoking questions and conversations are all about curiosity and connection, according to somatic psychologist and therapist Holly Richmond, Ph.D., LMFT, CST. “Conversation—not a monologue—is a direct route to someone’s head or heart, depending on the context,” she explains. When you ask someone quality questions—and show genuine interest in what they have to say—”you set up a system for a deeper connection going forward.”

And according to licensed marriage and family therapist Tiana Leeds, M.A., LMFT, without touching on these deeper topics, we’re left with our own assumptions about others, which, of course, aren’t always accurate.

“Conversation is our shortcut to understanding who someone is and deepening our connection to them,” she explains, adding that open communication can give us direct access to someone’s innermost thoughts and feelings—and also gives us the opportunity to be seen and known. As Richmond notes, good conversation is all about reciprocity.

Questions to ask yourself:

• What is my intention here?
• What are my core values?
• Which of my deep inner longings have I been ignoring?
• Who lights me up when I’m around them?
• Who drains my energy when I’m around them?
• When do I feel most alive?
• What am I feeling—nervous, anxious, trepidatious, excited, eager—and what is making me feel that way?
• How do I honor myself? Neglect myself?
• How have I grown as a person?

Deep questions for new friends:

• What’s been on your mind today?
• What are you excited about right now?
• Is there anything you’re worried about?
• How connected are you feeling to the world?
• What are you passionate about?
• What do you value most in a friend?
• What consistently brings you joy right now?
• What feels hard in your life right now?
• Is there a decision you’re contemplating that would be helpful to talk through together?
• What’s bringing you pleasure right now?
• What’s something difficult you’re working on?

Questions to ask a romantic partner:

• What feeling have you been experiencing the most lately?
• How connected are you feeling in our relationship?
• Are you sexually fulfilled?
• What could make our relationship even better?
• What makes you feel most loved?
• Is there something you care about for which you would be willing to risk your life?
• How can I be a better partner to you?
• What were you like as a child? As a teen?
• Tell me about the last time you felt lonely when you were with me.
• What are your dreams for your future?
• What makes you feel closest to me?
• Is there anything you are grappling with where I can help?
• What is your vision for a great relationship?

Thoughtful questions for family members:

• What excited you today?
• What are you feeling grateful for today?
• What was missing from your life this week?
• About what have you been proud of yourself for this week?
• What are you eager to feel more confident about in the next few weeks?
• What word would you use to describe our family?
• Do you identify with our family, or do you feel more like an outsider, and why?
• What family traditions do you carry on?
• Tell me about a time you did something you “weren’t supposed to” but it was worth it.
• Tell me about a family member of ours who I never had the chance to meet.
• What are our strengths as a family?
• What is your favorite present you’ve ever received?
• What are our values as a family?
• Any traditions that you were happy to say goodbye to?
• What do you think our family will look like in 50 years?

Philosophical questions:

• Where are you finding the most meaning in life?
• What do you imagine your legacy will be?
• How long do you think you’ll be remembered?
• What do you feel has been the most important thing you’ve done in life so far?
• What lasting impact do you know you’ve made in the world?
• What’s the most important quality a person can have?
• What does the world need more of?
• What does the world need less of?
• Do you think the sciences or art will be valued more in the next 50 years?
• Why is art important or unimportant?
• Will organized religion have a bigger or smaller place in society going forward?
• What is the meaning of happiness?
• Do you place a bigger value on helping yourself, your family, or the world? How so?
• By what standards do you think society should be judged?
• Do you feel like the world is changing for the better or changing for the worse?
• How so?
• Is there a motto or principle you live by?
• Is morality relative?
• What from the past is worth preserving?
• In what ways has society changed during your lifetime? What do you think caused these changes?
• Is it better to be realistic or optimistic?

The takeaway.

From being a good friend or partner to simply knowing how to keep a good conversation going, having an arsenal of thought-provoking questions is always helpful. Not only can you exchange interesting and new ideas, but you learn more about the people in your life, they learn more about you, and you’re able to deepen and strengthen your connection and understanding between each other, whether they be a friend, family member, or partner.

Getting the conversation started.

Conversations are going to look different depending on who you’re talking to and how close you are, but generally speaking, it’s always good to have an idea of why you want to have the conversation in the first place.

“Get clear about your own motives for starting the conversation,” couples’ therapist Alicia Muñoz, LPC, explains to mbg. “Are you motivated by pure curiosity? A desire to get to know someone better? A desire to build a stronger friendship? Do you have a specific goal in mind […] like a job interview?”

When you’re clear on your motive, she says, you can be open about it. People will naturally wonder why you’re striking up a conversation, “and being clear about it from the start creates trust,” she says. For example, if you were reaching out to a CEO on LinkedIn, you can explain from the get-go that you hope to work together. Or if you’re on a dating app, simply telling someone you’re interested in getting to know them can go a long way.

“Being upfront with people about your motives for starting conversations may feel vulnerable,” Muñoz adds, “but others often experience it as clarifying and refreshing. It fosters a genuine connection.”

Tips to keep things going:

1. Get curious.

Try to display genuine curiosity in the person you’re talking with. Licensed marriage and family therapist Holly Richmond, Ph.D., LMFT, CST, tells mbg, “I’m curious” is one of her favorite phrases. Think questions like “I’m curious about your…” or “I’m curious what you think about…” etc.

“People love to talk about themselves, and that ‘I’m curious’ question isn’t a judgment on your part,” Richmond says, “so there’s nothing the other person could get defensive about.”

As Muñoz adds, “Allow another person to experience your curiosity and interest in them. Let go of your agenda.”

2. Find common ground.

One of the quickest ways to start bonding with someone new is by finding common ground. “If there’s a moment to find synergy with a person,” Richmond suggests, “meaning shared likes and beliefs, that’s always a good way to go.”

It’s worth noting here that certain topics like politics, religion, and other potentially controversial subjects can lead to tension if you don’t already know where a person stands. If you want to avoid potential disagreements, you may wish to avoid such subjects. On the other hand, taking the risk to dive into these tougher topics may pay off if you find you have more in common than not.

3. Make sure it’s a good time to talk.

Sometimes people may not be the most forthcoming in conversation, and in some cases, this can be because it’s simply not a good time to talk. “If someone doesn’t seem to want to engage in a conversation with you,” Muñoz explains, “you could ask them directly, ‘Is this a bad time to talk? I want to connect with you, but I also want to respect this might not be a good time for you.'” This opens up the door for them to let you know where they’re at, and you should be able to gauge whether they’re interested.

4. Listen intently.

Really show you’re engaged and interested in what this person has to say. Not only will this make them feel good, but active listening can help strengthen all your relationships.

You can even practice with friends to improve your listening skills. A good rule of thumb for being a better listener: Don’t worry so much about what you want to say next. Just pay attention to what the person is saying.

“People generally open up more when they’re being seen, heard, noticed, and listened to in the little details of who they are and how they express themselves,” Muñoz says.

5. Ask open-ended questions.

Give people a chance to answer open-ended questions rather than giving straight yeses or nos. This is also another way of showing curiosity. As Muñoz notes, “Great interviewers know how to make people feel special by being genuinely fascinated by other people. Ask open-ended questions.”

As you listen, “notice their response without jumping automatically back to yourself, your experience, your interpretations of what they said,” she adds.

Tips for in-person conversations:

Pull from context clues. As you listen to someone talking, Muñoz suggests trying to “notice someone’s jewelry, the logo on their T-shirt, their overall energy level, their sense of humor, their way of expressing themselves, and celebrate that.”
Build on compliments. Just as people love to talk about themselves when you give them the opportunity, “People also love compliments,” Richmond notes. Finding something to compliment, whether it be something they’re wearing, or something more personal like their overall energy, can help the person soften and open up. You can combine this with tip No. 1, a question like, “I’m so curious where you got that fantastic bag,” Richmond offers as an example.
Have good eye contact and body language. Body language is essential. People can easily pick up on when a conversation has run its course by the way we position our bodies, how much eye contact we’re making, and our tone of voice. “Really make sure you’re looking the person in the eye, your body is facing them, and your arms aren’t crossed,” Richmond says.

Tips for texting conversations:

Don’t fret if they’re not the best texter. Texting isn’t for everyone, and it’s easy to overthink short replies and delayed response time. Whoever you’re texting could also be busy and not in a place where they can be totally engaged with their device. You can always ask whether it’s a good time, or if they’d rather talk on the phone or meet up IRL. “If a person answers in a monosyllable, don’t give up,” Muñoz says. “Keep attending to them. Maintain a warm, open stance. Don’t let your own insecurities break the connection.”

Be direct. One downfall of texting is the chance for things to get lost in translation. Your best bet is to be direct. “In texts,” Muñoz explains, “it’s important to spell things out that might otherwise be communicated in someone’s tone of voice or body language.” For example, you could say, “I’ve been thinking about you and wondering how you’re doing. I’d love to hear anything you want to share!” she adds.

Use emoji. OK, emoji aren’t for everyone. But if you want to communicate your message clearly and directly, one way to do so is through emoji—especially if we’re talking about messaging someone on a dating app. Research shows people who use emoji actually have more first dates, and it has everything to do with the way we respond to those little facial expressions when we can’t actually see the visual cues from whom we’re talking with otherwise. They fill in those gaps, so give ’em a try!

Specific topics and questions:

1. Their upbringing

It goes without saying that our childhood shapes us into who we become in so many ways. Basic questions about where someone grew up can tell you a lot about a person and is also a good chance to find out where the two of you may share similarities (or differences).

Some questions to ask:

• Where did you grow up? What was it like?
• Did you like growing up there?
• What do you think is the best thing about your hometown?
• Would you ever move back home? (Or if they live there, do they want to move?)
• Where are your favorite places in town?

2. Weather and seasons

Yes, this might be considered small talk, but when in doubt, dealing with the weather is a universal experience, and everyone has something to say about it. There’s a reason it always comes up! Plus, someone’s thoughts on the weather can tell you what they like as far as the seasons and seasonal activities, what kind of day they’re having, etc.

Some questions to ask:

• Do you like rainy days, or do you find them kind of drab?
• What’s your favorite season and why?
• What are your favorite things to do in fall, winter, etc.?
• What does a day of perfect weather look like to you?
• If you could skip any season, which would it be?

3. Hobbies and interests

Who doesn’t love to talk about what they’re passionate about? Getting curious about someone’s hobbies and interests shows you want to understand them, and you can also try to find some common ground here. Maybe you notice they posted a picture skiing or a newly completed art project, so you ask them about that. People are usually happy to share the things that bring them joy.

Some questions to ask:

• What’s your favorite way to spend your free time?
• What’s one topic you want to know everything about?
• Is there a particular hobby you’ve been dying to pick up?
• What’s the last internet rabbit-hole you went down?
• Did you have any hobbies as a kid you’d like to pick up again?

4. Books, music, TV shows, and movies

At least one of these forms of media is likely a significant part of someone’s life. People get super passionate about their favorite musical artists, TV series, and so on, so ask them about it! You may find you both love the Lord of the Rings series, or you’re both big fans of classic rock.

Some questions to ask:

• What kind of music do you like to listen to?
• If you could live in any TV show’s or movie’s universe, which would it be?
• Do you have an all-time favorite book or author?
• What’s the best concert you’ve ever been to?
• Who’s your favorite fictional character of all time?

5. School and work

Asking about school or work is bound to come up as you’re getting to know someone. It’s always good to know what someone’s goals are, what they’re studying or have studied, and how that ties into their story. Just pay attention here if the tone shifts when you bring these things up, as school and work can be sources of stress. If it seems like they don’t want to talk about it, you can always redirect the conversation:

• What did you go to school for, and what made you decide that?
• Did you ever think you would be a [insert career], or did you want to be something else growing up?
• What’s your biggest professional goal right now?
• What’s your favorite class right now? (Or if they’re working, what is their favorite part about their job?)
• Do you ever feel called to try something else career-wise, or are you happy with where you’re at?

The bottom line.

Conversations aren’t everyone’s forte, and that’s OK. At the end of the day, showing you are actively listening, offering nonjudgmental and open questions, and simply being kind and forthcoming will never steer you wrong when chatting with someone, whether they’re a new friend or an old one. Try practicing with people you’re close with to strengthen your conversational skills. And when in doubt, a compliment never hurts.

We’ve all been there—but the truth is, it is totally possible to make new friends, no matter how old you are. Here’s advice on how to make friends as an adult, from three relationship experts:

1. Approach with positivity.

According to board-certified psychiatrist Roxanna Namavar, D.O., the way we perceive the world frames our whole life. If you go into social scenarios or approach making new friends with negativity, you aren’t going to get too far. This is the law of attraction 101—we have to focus on what makes us feel good. If all we focus on is our lack of new friends, we’re reinforcing that reality.

“When we start to focus on doing things that make us feel good and engage in a way that increases positive feelings, it makes it easier to see and connect with other people we resonate with,” she adds.

2. Create a life for yourself that you enjoy.

To that end, Namavar stresses that the best thing you can do for yourself to make new friends is to create a life you enjoy. “Like attracts like,” she notes, and “the more engaged we are with life, the easier it is to go out and meet people. When you do things that make you feel good, you end up finding people who enjoy the same things.”

3. Find a group that interests you.

Yes, this may be a little difficult in the age of COVID-19, but there are still plenty of virtual interest groups you can take advantage of right now. As psychologist Nicole Beurkens, Ph.D., explains to mbg, “One of the easiest ways to connect with people who might be friendship material is to engage in group activities around your interests.”

“One of my favorite ways to make friends as an adult is Meetup,” says somatic psychologist Holly Richmond, Ph.D. “There’s also My Social Calendar.”

Engaging in things you enjoy, whatever they are, “can reduce fears of awkwardness by giving you something to focus on besides the people involved,” Beurkens adds.

For a little inspiration, here are just some of the activities you can consider, offered by Beurkens, Namavar, and Richmond: Take a new yoga class, join a local hiking group, try a cooking class, attend a spiritual or religious service, practice with the church choir, check out a local sports club, join a committee at work, scope out a crafting workshop, join a book club or volunteer with a local charity.

4. Lead with curiosity.

When we’re meeting new people, our insecurities can get the best of us, Richmond explains—but it goes both ways. It’s important to remember a new friend is just a person like you, who’s also got their own insecurities.

“Instead of talking about yourself or thinking you have to impress this person, lead with curiosity and ask questions about them,” she says. “We’re all so in our head, so if you can help get someone out of their head a bit, it’s generally really endearing.”

5. Look to your network.

In the age of social media, there are innumerable casual acquaintances always available at our fingertips. Why not reach out to one of them? As Richmond tells mbg, relationships are always evolving: “You can know someone for years and one day just click,” she says. “Timing is everything, so give those old relationships a new chance or a new view.”

Mutual friends are a great place to start as well, Namavar notes. “Sometimes it makes it easier to be social if a friend is with you that you already feel comfortable with,” she says. Plus, if they already get along with one of your friends, there’s a good chance you’ll like them too.

6. Say yes.

You might have to go outside your comfort zone and try new things to make new connections. “The key is to be willing to put yourself out there to engage with other people you don’t know,” Beurkens says. Of course, this can be intimidating, “especially for people who are shy or experience some social anxiety,” she adds, “but taking the risk to meet new people is what leads to the reward of developing new relationships.”

As much as your inner social butterfly allows, say “yes” when you receive an invite. You never know until you try, and the more you put yourself out there, the more people you’ll meet. Richmond recommends letting friends and family know you want to make new friends as well, “So they can put feelers out for you, and invite you to things they’re going to.”

7. Don’t be afraid to initiate.

Making a friend is a two-way street, so don’t be afraid to initiate. The other person could be just as hesitant to reach out, too. Things like a simple compliment or finding a similar interest are great places to start, Namavar says. “Also, asking somebody for a little bit of help,” she adds, “opens the door to soften the interaction.”

Similarly, if you’re single and dating new people but it’s not working out romantically, you can always try initiating a friendship. Richmond notes she knows lots of people who’ve become friends with someone they went on a date or two with but didn’t vibe with romantically. “Go into dating with an open mind—it could be something different,” she says.

8. Get vulnerable.

“We’re programmed to be afraid of rejection, but no connections that are worthwhile happen without vulnerability,” Richmond says. For this reason, having a strong enough sense of self so you can be OK with a friendship not working out is important. Don’t be afraid to be yourself—otherwise, how will you make friends who see and accept the real you?

“Not everyone’s going to like you, but as we get older, you can accept that not everyone needs to like you,” she adds. And when you live your truth, “then you can find the people who do,” she says.

9. Be patient.

And lastly, know it takes time to build strong relationships. Be ready to give things time to naturally unfold and for the friendship to blossom. It’s not a marathon—and when it comes to friendship, it’s always quality over quantity. “The key is to have at least one or two people in your life you can rely on and feel connected to,” Beurkens notes. You don’t have to overwhelm yourself by booking your calendar to the brim. Start by simply finding one new person to reach out to, and take it from there.

The bottom line.

Friendships are one of the most enriching parts of our lives, and as we get older, making new ones can seem like a challenge. But if you’re seeking new, meaningful connections in your life, it starts with a commitment both to meeting new people and a commitment to yourself.

Once you decide to make new friends, put yourself out there and get involved in an activity that really lights you up. You’re bound to meet someone new. Tell that cool girl in your yoga class you like her leggings, or introduce yourself to your neighbor down the street that you’ve always thought seemed nice. Every interaction is a chance for a new connection when you’re open and looking.