Friendships are hard, really hard. If I am being completely honest, they have always been hard for me. Now that so many of us are stepping into this new era of adulthood, it feels even more confusing. Half of the time I just want to yell, “What does being an adult even mean?” because I genuinely have no idea. I feel just as lost as I did when I was five on my first day of elementary school, or 13 walking into high school for the first time.
Making friends and actually growing those friendships into something meaningful sounds great in theory, but in reality, it is harder than anyone tells you. As a woman, it feels even more complicated. The good old days of childhood – when you could compliment someone’s shoes or say hi and instantly declare each other BFFs – are pretty much gone. The older I got, the more obvious it became that you cannot just walk up to someone and ask them to be your best friend. There are all these unspoken rules, worries, and social layers that make it feel more complicated and competitive than it needs to be. On top of that, with social media and our devices being the main way we communicate, it adds a whole new layer of distance. Somehow, we are more connected than ever, but making real friends and forming deep, trusting bonds feels harder than ever.
So, this is what I want to talk about today: how to grow your connections within the friendships you have and actually deepen them. A big part of that comes from being more present and intentional in every sense of the word. I know that can sound intimidating or even a bit made-up, but I promise it is not. The methods and questions I am about to share have helped me build some of my closest friendships, the ones that have carried me through thick and thin, good days and terrible ones.
Even though communication and socializing are supposed to be big, celebrated parts of our culture, day-to-day life somehow feels lonelier and more surface-level than ever. Personally, I refuse to settle for that. I want the sisterhoods and friendships we grew up watching on TV or reading about in books. I want to find my Monica and Phoebe or my Nick, Schmidt, and Winston. Consider this my official petition to bring deep feelings back into everything we do: friendships, relationships and even the smallest everyday moments. I want us to bring back intentional living.
With that in mind, I am going to walk you through some activities and questions that truly shape the foundation of your friendships. I will start with some introductory questions that help you build healthy habits and boundaries early on. Then, I will share a few activities and deeper questions that can strengthen friendships that might feel a little stuck or lack substance. These questions can also help you see whether you and a friend are putting in the same level of energy, which is something most of us wish we knew sooner.
So let us start with the first step toward building intentional, present, and meaningful friendships.
How to Make New Friendships More Intentional
Beginning a new friendship is kind of like planting a seed. You cannot force it to grow, but you can give it the right conditions. The things we talk about early on can tell us so much about who someone is and how we might fit into each other’s lives. These questions and small actions are not meant to interrogate anyone. They simply open the door to deeper connections right from the start, instead of keeping the conversation stuck in the usual “What program are you in?” routine.
Below are some of my favorite questions and habits to use when you are just getting to know someone and want to build something real with them.
Ask About Their Dreams: “If you could have any job in the world, what would it be and why?”
This question is simple, but it tells you a lot. It shows what excites them, what they value and what they imagine for themselves when no one is watching. People light up when they talk about their dreams and that energy is contagious. It also lets you see their ambition, creativity or softness and how those things blend with your own energy.
Ask What Is Bringing Them Joy: “What are you most excited about right now?”
This question helps you move out of surface-level small talk. It opens a window into their current world and what matters to them. You also learn what you can cheer them on for in the future.
Ask About the People in Their Lives: “Tell me about some of your friends. Who are they and what do they mean to you?”
This question reveals who they surround themselves with and what kind of friend they are. You hear how they talk about the people they love and what they appreciate in relationships. If they speak kindly and fondly about their friends, that is always a green flag.
Ask Who Their Inspiration Is: “Do you have any role models? Who are they and why do you look up to them?”
Role models reveal someone’s inner compass. You learn what they admire and what qualities they want to grow within themselves. This helps you understand their values and the things that shape how they view and move through the world.
Ask About What Makes Them Feel Seen: “What is the nicest thing someone has ever said to you?”
This question is gentle and surprisingly intimate in the best way. It tells you what they crave and what makes them feel appreciated. Some people feel seen when complimented on their strength, others when told they are thoughtful or funny. Knowing this early on helps you understand the little things that make them feel valued, so you don’t have to guess in the long term.
Ask What Is Misunderstood About Them: “What is the biggest misconception people have about you?”
This question gives someone the space to explain themselves and share a side of them that the world does not always notice. People often soften when they answer this. They drop their guard a little and that is where the real connection starts.
Ask What Has Had an Impact on Them: “What is a TV show, movie or book that really made an impact on you?”
This question opens the door to personal stories, emotional connections, and the experiences that shape someone’s worldview. People reveal a lot through the media that stayed with them.
Take Initiative Early On:
At the start of a new friendship, taking initiative matters more than most of us realize. Make the plans. Suggest getting coffee or studying together. It shows effort and presence which always makes someone feel wanted and welcomed.
Follow-Up After Hangout’s:
This is such a small thing, but it makes a huge difference. Send a quick “I had a great time” or mention something they said. It shows that you were listening and that the moment mattered to you.
The “How Did It Go?” Text:
If they had a test, date, or presentation, check in afterwards. These messages make people feel seen and remind them that you care beyond the moment itself.
Ask For Advice:
A great way to break away from small talk is to ask for advice or to share something you are struggling with. Vulnerability creates more vulnerability. When you trust someone enough to open up, they often do the same. This also shows that you value their perspective.
Genuine Complements Only:
Only compliment people when it is real. Try to go deeper than a simple, “I love your outfit.” Mention something you genuinely admire about their character or energy. These compliments stay with people for a long time and help them feel noticed in a meaningful way.
Now that we have talked about starting new friendships with intention, let’s move on to how to deepen your current friendships.
Deepening The Connections in Your Existing Friendships
Once a friendship starts to grow, the real magic comes from the moments where you both open up a little more and let yourselves be seen. Deep friendships are not built from grand gestures. They come from small questions, quiet honesty, and being consistent with each other. These questions can help you move past surface level conversations and into something real.
Ask How They Make Decisions: “When you need to make a difficult decision, do you tend to lead with your head or your heart?”
This question can open the door to some of the most meaningful conversations. People often reveal the things they are currently wrestling with when they explain how they make choices. You learn how they think, what scares them and what they value when life feels uncertain. It also shows you how your own way of making decisions lines up with theirs.
Ask What They Are Prioritizing Currently: “What are you currently prioritizing in this season of your life?”
Everyone is always in some kind of season, and it changes more often than we realize. When you ask this, you get to hear what matters most to them right now. Maybe they are focused on school, their mental health, or rebuilding their confidence. Knowing this helps you support them in a way that actually matches where they are.
Ask What Gives Their Life Meaning: “What makes your life feel purposeful?”
This question invites someone to slow down and reflect. The purpose is different for everyone. For some, it is creativity. For others, it is helping people or feeling connected to a community. Hearing what gives their life meaning helps you understand what they chase and what fills their heart. It also creates space for both of you to talk about how purpose shifts over time.
Ask What They Are Daydreaming About: “What are you currently daydreaming about?”
Daydreams reveal the softer parts of a person. They show you their hopes and the things they wish they had more of. It could be a future career, a trip or even a feeling they miss. These conversations feel light at first, but they often lead to deeper moments of connection.
Ask What They Need More and Less Of: “What do you need more of and what do you need less of?”
Everyone has something they are craving and something they are exhausted of. When you ask this, you get a clear picture of how to show up better. Maybe they need more rest or more encouragement or more fun. Maybe they need less stress or less comparison. These answers help you understand what support looks like for them.
Ask About Honesty: “When was the last time you told someone how you really felt?”
This question gently encourages vulnerability. People often hold a lot inside, and this gives them permission to open up if they want to. It creates a safe space where honesty is welcomed instead of avoided. It also tells you how comfortable they feel being real with others.
Ask About Their Trust Being Broken: “What makes you lose trust in someone?”
Trust is the foundation of every meaningful friendship. When you understand what breaks their trust, you learn how to protect the friendship. It also helps you talk about boundaries, which is something most people struggle to bring up on their own.
Explore Their Relationship with Peace: “Is your need for revenge greater than your need for peace?”
This question sounds intense, but it often leads to honest conversations about conflict, forgiveness, and how they move through hard emotions. People who want peace usually value harmony, while people who crave justice might value honesty and accountability. Neither is wrong, it just shows you the kind of emotional world they live in.
Be Intentional with Your Time Together:
Deep friendships grow when the effort goes both ways. Take turns planning hangouts. Make the plans clear with the time and place, so no one is left guessing. You do not need big outings either. Activities like hikes, quiet picnics, walks or meditation offer a calm space where you can be vulnerable and present without distractions.
Cooking together is also a great way to bond. Even if neither of you can cook, it creates laughter and teaches you how to handle small challenges together.
Show Up Consistently:
Be present in the simplest ways. Carve out a regular time for a walk or a weekly coffee. As life gets busy, it is easy to drift, so doing at least one check-in a week keeps you active in each other’s lives.
Express Your Appreciation:
You will never regret telling someone you appreciate them. Say it out loud or show it in small ways. If you give gifts, make them thoughtful. Pay attention to what they talk about or the things they love and choose something that reflects who they are.
An Ending Note
At the end of the day, friendships grow when we choose to show up with honesty and softness. None of this is about being perfect. It is about being present and showing a little more intention to the people who make life feel less heavy. The truth is that most of us are just trying to feel seen and understood in a world that moves too fast.
If you try even a few of these questions or activities, you might be surprised by how quickly something real starts to form. Deep friendships are built in quiet moments and small efforts that say I care about you.
So, take a breath and give yourself permission to try. You deserve connections that feel steady and gentle. You deserve people who meet you where you are.