The Art of Initiating Adult Friendships

Why making friends as an adult can feel harder than dating and why I’m still learning how

There are some roads in life that look familiar from a distance… until you actually start walking them.

Friendship has been that road for me.

From the outside, making friends seems simple. We’re taught the basics young: be kind, share, listen, play well with others. But nobody really teaches you how friendship changes once you become an adult. Nobody tells you how much courage it can take to say I like your energy… let’s stay connected.

And somehow that tiny sentence can feel heavier than anything.

My work is unconventional because I’m unconventional. I’m not exactly a life coach. I’m not only a stylist. I’m not only an artist or designer either. I’m someone building a life through expression, creativity, reinvention, and example. I live visibly. I create openly. I share honestly. And through all of that, I’m simply trying to become the best version of myself.

Not the perfect version.

Just the most honest one.

And I’ve learned something in that process: not everyone wants that for themselves, and not everyone will want that for you either. That used to hurt me more than it does now. These days, I’m more interested in connecting with the people who do.

The people who crave depth.

Connection.

Growth.

Laughter.

Realness.

But if I’m being truthful, one of my biggest challenges in life hasn’t been business.

It hasn’t been art.

It hasn’t even been motherhood.

It’s been friendship.

That’s a hard thing to admit out loud.

I think many people struggle with friendship privately, but very few say it publicly. We talk about relationships. Marriage. Parenting. Career. Healing. But friendship? Adult friendship can feel like the silent challenge no one wants to confess they’re still figuring out.

I know I’ve lost incredible people in my life because I didn’t fully understand what friendship meant at the time. Sometimes I misunderstood closeness. Sometimes I overgave. Sometimes I withdrew too soon. Sometimes I expected people to read things I never said out loud. Sometimes I waited too long to reach back.

And sometimes… I froze before something beautiful could even begin.

I can stand next to someone in line at Marshalls or HomeGoods and connect instantly.

We’ll laugh.

Trade stories.

Talk style, life, relationships, random things like we’ve known each other forever.

For twenty minutes it feels effortless.

Like maybe this could be someone I’d genuinely enjoy knowing.

And then comes the moment.

That tiny opening.

The moment where one of us could say:

“Hey, we should exchange numbers.”

Or

“Are you on Instagram?”

Or

“Let’s grab coffee sometime.”

And that’s usually when I choke.

Every single time.

I smile.

I hesitate.

I let the moment pass.

And I walk away wondering if I just missed out on a really good friendship.

Recently this happened while I was standing in line at Marshalls HomeGoods. There was this incredible woman behind me. Our conversation flowed so naturally. Easy. Fun. Familiar. Like friendship in its earliest rawest form.

And still… I couldn’t bring myself to initiate future contact.

Part of it was shyness.

Part of it was timing.

Part of it was my boyfriend standing there teasing our banter.

But deeper than that…

It was fear.

Fear of being misunderstood.

Fear of seeming too eager.

Fear of overselling myself.

Fear of rejection.

Fear of asking for more than what the moment naturally wanted to give.

And maybe even fear that adult friendship chemistry doesn’t always mean adult friendship compatibility.

Because friendship as an adult feels different now.

When I was younger, friendship often happened through proximity school, neighborhoods, work, mutual people.

Now I’m seeking something deeper.

Something intentional.

Friendships with substance.

Friendships where we pour into each other.

Friendships where ambition isn’t threatening.

Where softness isn’t weakness.

Where honesty feels safe.

Where depth doesn’t scare people away.

And maybe that’s why I hesitate now.

Because I’m no longer looking for people to simply pass time with.

I’m looking for people to share life with.

And that can feel vulnerable.

So I’m learning something:

Maybe friendship doesn’t always begin with certainty.

Maybe it begins with courage.

Maybe it begins with sending the text.

Asking the question.

Offering the compliment.

Following up after the conversation.

Making the first move without needing the outcome guaranteed.

Maybe friendship doesn’t need lightning to strike twice.

Maybe it only needs someone willing to say…

“I enjoyed meeting you.”

“Let’s stay connected.”

“Would you want to do this again sometime?”

And maybe next time…

I’ll be brave enough to say it first.