The 5 Most Important Conversations To Have With Your Bestie

Everyone needs a good heart-to-heart sometimes. 

One of the most tried-and-true ways to know if you’re really close with someone is whether or not you can sit with them comfortably in silence. There is something magical about sitting around with your bestie, not needing to say anything at all to fill the room or validate the friendship.

Having said that, the occasional heart-to-heart is also imperative to not only maintain the friendship, but to nurture it and help it grow. Some things in life are scary to tackle with just about anyone, while others come more naturally. But there are ways to approach all of those things and conversations you can have with your closest friends to become even closer than you already are.

What are they, you might ask? New York City-based mental health counselor and psychotherapist Lili Knutzen, MA, MED, LMHC  says the “most difficult conversation topics are either painful for us to examine for ourselves, or we fear that our friends will be angry or hurt to hear our point of view, especially if it opposes their value system.”

But even if your friend and you have differing opinions and viewpoints, Knutzen says “if you have to filter out your conversations with your closest friends, reevaluation of your relationship may be in order.”

Here are some other conversations — both big and small — that are imperative for getting closer with your bestie.

The One About Your Communication Styles

It might seem far-fetched to have a conversation with your friends about having conversations, but understanding how the other person does (or does not) communicate is key to understanding each other, and working things out in the event there is a disagreement or miscommunication.

Irene S. Levine, PhD, psychologist, author and friendship expert, producer of, says it is key in preventing misunderstanding. “If people have very discordant communication styles and can’t understand one another’s it can lead to frequent misunderstandings.” If you’re the kind of person who gets overwhelmed by a text or call during work hours, tell your friend. “Some people don’t want to be phoned without being asked whether it’s a good time to talk, others don’t care,” Levine says.

The One About Spending Money

Money is a point of contention for people both in relationships and in friendships. Things like splitting the bill at dinner or feeling like you’re missing out on something if you don’t go regardless of whether or not you can afford it can be stressful and put a rift between you and your best friend.

Levine says it’s important to be honest about what you can and cannot do. “She earns more than you do (or vice versa) and she likes to eat at top-shelf gourmet restaurants while you have to stick to a limited budget. She wants to stay at luxury resorts when you vacation together and you prefer modest Air Bnb? How are you going to negotiate that chasm? You need to discuss your values about money before she orders a pricey bottle of champagne, expecting to split the tab.”

The One About Her New Boyfriend

The beginning of a new relationship is exciting, but it can also take a toll on the long-standing relationships you already had — the ones with your friends. It is easy to get caught up in, and while you should feel both empowered to enjoy that and understanding if your friend is enjoying it, it’s still completely OK to approach her if you feel neglected in the friendship.

There is a right and wrong way of doing that, though. Coming to your friend defensively will only make her react. If you delicately approach the situation, explain that you miss your friend and want to make time to spend just the two of you, she will likely be more open and accepting to the suggestion.

The One About Her Health

While it can be scary to share information about an illness — whether physical or mental — it’s imperative to feel like you have people you can trust and talk to about any and everything that is going on in your life. Levine says if you don’t let if a friend is keeping something like her health away from you, you might start to think that the person is unreliable, and it might start to bother you and prevent you from being there for her. Having said that, Levine says it’s important to know when to take things a step further than just conversation. “If the help your friend needs is more than can be provided by a friend, refer that person to professional help.”

The One About The Little Things

The big conversations are important, but something to keep in mind is that in order to get to those big topics, people need to feel like they can trust and rely on you. That,  Leonard Felder, PhD, author of More Fully Alive: The Benefits of Using Jewish Wisdom for Responding to Stress and Overload says, comes through in very small ways. “A true friendship is where someone calls or writes in and checks in every few weeks at lunch and says ‘how are you?’ ‘How’s it going with that (challenging situation) you told me about last time we talked?’ In doing those seemingly tiny, but mighty things, Felder says “you are building a long-time ally for all the ups and downs of life.”

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