There are tall ships
There are small ships
But the best ships
Are friendships…
Unless, of course, they’re not.
Fall has a way of making us want to clear things out. Our closets. Our calendars. The habits we meant to leave behind months ago.
But what about our friendships? When was the last time you checked in with how the people around you actually make you feel?
Social connection is the fifth pillar in my Five Pillars of Self-Care and Well-Being, because nurturing healthy, supportive friendships is itself a powerful form of self-care.
And sometimes, self-care means acknowledging when a friendship has become painful.
Perhaps as you’re reading this, you have someone in mind.
To be honest, I’ve been fortunate not to have experienced many toxic friendships over the years. I was raised to talk to everyone, and I’ve always had friends in many different circles. Cliques were never my thing. But I know that friendships can become painful, even when you enter them with an open heart and the best intentions.
Over the years, readers have shared stories with me about broken trust, gossip, and friendships where they give so much and receive very little in return.
And that can hurt. Especially when there’s history.
What a nurturing friendship looks like
While in Florida years ago, I was having one of those overwhelmed mom moments. My girlfriend Kara looked at me and said quietly, “Bring me both your boys, and goodbye. Walk away, grab your beach chair, and go read your book.”
THIS is nurturing.
She saw what I needed and offered to help.
Friendship doesn’t have to look exactly like that, of course. But there should be room for your needs, your feelings, and your life, too.
Every friendship has difficult moments. People cancel plans. They say the wrong thing. They go through hard seasons when they have less to give.
What matters is whether hurtful behaviour becomes a pattern, and whether there’s room for honesty, accountability, and change.
It’s time to give your friendships a fall check-in. Who’s with me?
Six friendship patterns worth paying attention to
1. They repeatedly let you down
We all need grace when life gets in the way. But if someone constantly breaks promises, cancels at the last minute, or leaves you waiting without a word, it’s reasonable to feel frustrated.
What you can say: “I understand that plans change, but when you don’t let me know, it affects my day. I’d really appreciate a heads-up next time.”
Then pay attention to what happens next. An apology matters. Following through matters, too.
2. There’s only room for their life
You know what’s happening with their partner, their work, their children, and their neighbour’s renovation. But do they know what’s happening with YOU?
Friendship won’t always be an equal exchange in every conversation. Sometimes one person needs more support. But over time, both people deserve to feel heard.
What you can say: “I want to be here for you, but I’ve been going through something too, and it would feel good to talk it through with you.”
3. Your private business becomes public conversation
You share something in confidence, only to discover that someone else has heard it.
Whether it’s sharing secrets or spreading rumours, broken trust can change how safe you feel in a friendship.
What you can say: “I shared that with you privately. I felt hurt when I found out someone else knew, because I thought it would stay between us.”
You’re allowed to be more selective about what you share while you decide whether that trust can be rebuilt.
4. Everything becomes a competition
You share good news, and somehow the conversation turns into what they’ve accomplished. You mention a struggle, and theirs is immediately worse.
A little friendly competition can be fun when you both enjoy it. Constantly having to defend, downplay, or compare your life is exhausting.
What you can say: “I was excited to share this with you. I was hoping we could celebrate it together.”
You deserve to enjoy your good news without feeling you need to make it smaller.
5. They constantly find fault
There’s a difference between a friend who tells you a hard truth with care and one who repeatedly makes you feel small.
The digs. The backhanded compliments. The “I’m just being honest” comments that leave you questioning yourself.
What you can say: “I value your honesty, but that comment felt hurtful. I would appreciate you not speaking to me that way.”
Being close to someone doesn’t give them permission to be unkind.
6. Your boundaries become a guilt trip
You say you can’t meet, and suddenly you’re a terrible friend. You need a quiet evening, and they make you feel selfish.
A friend can be disappointed without making you responsible for fixing that disappointment every time.
What you can say: “I’d love to see you, but tonight doesn’t work for me. Can we find another time?”
You don’t need a lengthy defence every time you say no.
So… do you stay, step back, or let go?
This is the part that can leave us on the fence, especially when a friendship has been part of our lives for years.
Start by asking yourself:
- Can I be myself around this person?
- Is there room for my needs as well as theirs?
- Can I bring up something hurtful without being mocked or dismissed?
- When we talk about a problem, does anything actually change?
If the friendship matters to you and you feel comfortable doing so, have an honest conversation. Be specific about what happened, how it affected you, and what you need moving forward.
Then give yourself permission to notice their response.
Some friendships can grow through a difficult conversation. Others may need more distance, fewer expectations, or firmer boundaries. And some may need to end.
You don’t have to make a dramatic announcement. You can step back without gossiping, retaliating, or recruiting mutual friends to take sides.
And while you’re thinking about the friendships that hurt, remember to nurture the ones that feel good. Call the friend who checks in. Make the coffee date. Be the person who listens and celebrates, too.
If a friendship is causing you ongoing distress, talking with a therapist can help you work through your feelings and decide what boundaries you need.
A fall friendship cleanse doesn’t have to mean cutting people out. It can mean getting honest about which relationships need care, which need boundaries, and which you’re ready to release.
If you’re working through this right now, I’m sending you lots of love. You can miss someone and still know that the friendship needs to change.
Have you ever had to step back from a friendship—or did an honest conversation help you find your way back to each other?
P.S. If you’re craving more social connection, nurturing friendships, and a little time for YOU, why not join me next month at Reset & Thrive at Canyon Ranch in Lenox, October 15–18? Think spa time, beautiful fall hikes, meaningful conversations, laughter, and space to exhale. The ultimate girls’ getaway with a little more intention. Come with a girlfriend or come on your own—I’d love to welcome you.
