How to Decipher When to Challenge or Cheerlead Your Friend

Back in 2015, my friends and I impulsively spent an exorbitant amount of money to see Taylor Swift on her 1989 World Tour. There was so much traffic driving down to San Diego that we regretfully missed sweet Shawn Mendes’ set, but we knew there were still surprise guest performances to look forward to. And surprised we were - Swift brought out “Sk8er girl,” Avril Lavigne and Jamaican reggae artist, OMI, to sing their respective crowd favorites and dance with her.

And while no one could ever restore the damage done to my heart that night due to missing the Canadian heartthrob opener, I enjoyed watching OMI maximize his time on stage, putting on quite the show as he sang his 2012 hit song, “Cheerleader”. Besides being a catchy summer bop, I’ve always liked the song, “Cheerleader” because of the lyrics and concept behind it: OMI lauds the girl he’s finally found to be “always right there when [he] needs her.” Whatever the relationship dynamic, the title and role of a cheerleader in the lives of those around me personally brings great pride and joy.

Truly the best friendships and relationships spring from deep wells of support, loyalty, and commitment, or simply put, by showing up for people when it matters most.

But is there a time and place where we choose not to don that title? I’ve been mulling over the difference between being a cheerleader versus when it comes time to put down the pom poms and step into the trenches with a friend.


Surely there are moments we hang on the sidelines, sensing the necessity of keeping some distance as we watch a friend make their own decisions and forge the paths that only they can. Yet what also unfolds is the adage of “seeing something, saying something” – meaning, when duty calls, we push trivialities to the side and get on the field. Out of love and care, we champion our people by sharing reminders of the harsher truths.

I’m still stuck on a friend’s vulnerability offered to me recently - she expressed that my “calling out” and push of her to be mentally tougher had weathered her down; she claimed she needed less of the sharpening and more of the rallying. I was rendered speechless. I had seen behaviors and patterns of thinking in this friend that I had deemed unhealthy, and even at odds with the best version of herself I knew she was capable of aspiring towards. Yet despite acting from what I know to have been a good intention, I had blundered my way through an apology for inadvertently hurting her. I had hurt her by not recognizing that what she needed most was silence, validation, and a firm grip of solidarity.

So in one hand, there’s the impending danger of being too controlling when stepping in. In the other lies caution for a potential level of passivity with cheerleading.

How does one discern the difference? Must a good relationship consist of a dynamic that healthily vacillates between the two dispositions? While I’d never claim to be an expert on the subject, here are some thoughts I’ve found to have aided me personally in my own friendships as I’ve stumbled and learned along the way.


In Your Corner

Intrinsic in the action and definition of cheerleading is joy. When we cheer for someone or something, our whole body is involved in this celebration and support - hands lifted, noise levels reach absurdly high decibel levels, emotions run rampant. Our loyalty cannot be denied.

When they let us know of a big event coming up, share a point of stress and/or excitement, allude to something bolstering their anxiety, we follow up. We check in with a text, we send a photo of a past fun memory, we leave a voicemail - anything that denotes in the busyness of our own lives, we are taking the time to think of them. We send flowers, a Postmates dessert delivery, their favorite snack left on their doorstep, we make plans for coffee. I had a friend that once dropped everything to drive an hour to me because she read right through my texts and knew what I needed was my favorite ice cream and a hug.

That’s the beauty of being “right there when [they] need.” I believe our friends and loved ones should be able to know exactly where to look to find us and see us, rocking jerseys with their names inscribed and holding signs that communicate the same allegiance on the good days and the bad. And maybe that’s just it - they decide when to look over and see us when they need encouragement the most. Our job sometimes can be to just keep on swimming, which in many cases, is just to keep on cheering.


In the Trenches

But there are times when we cannot sit still and be silent - and this ranges from person to person. We start to see changes or habits or new practices in others that they could define as growing pains or self-discovery, but maybe we think or feel otherwise. Sometimes we wait before we say something directly and first reach out to others in our community to ask if they see the same thing. We may feel that the lingering feeling of regret for not speaking up is not worth the tension, albeit fleeting or permanent.

I always want to check my bias and personal opinions at the door, which is why it’s helpful for me to check with my mutual trusted friends before confronting another. Am I wanting this person to conform to my own ideal of how they should be and operate, or truly to their own best person? (I typically ask my mom to weigh in since she’s the wisest of them all - she’s seen plenty of life to know which battles to take on and which ones to let go. God bless her.)

Questions to ask ourselves before we challenge a friend could be as simple as:

  • “Can I share my opinion without compromising my loyalty?”
  • “Does this thought truly challenge my friend in love or does it puff up my own ego?”
  • “Will it be worth it to say, ‘I told you’ later or ‘I’m for you’ now?”


A situation you’re in might warrant confrontation, which more often than not, could be tethered to defensiveness or disregard. Still maybe we persist, maybe we drop it, or maybe we take our observations to the grave.

If the challenge is sourced and rooted in love, I think one of the toughest, but most important, things we can do is to be a lens for our people.

Sometimes I have failed to see the truth in myself, and my best folks have come alongside me to shake me out of my dark haze. Even if I was at first sensitive to their constructive sharpening, the life-giving words that they spoke grounded and sobered me. I knew that I could trust their intentions because of how they had proved themselves time and time again.


No Formula

We could stay on the sidelines and get it wrong. We could open our mouths and mess it up. There is no formula, magic potion or instruction manual on how to do friendships perfectly. I don’t know that there’s a way to love hard and come out unscathed. But as I recently heard Levi Lusko say, “Even our low moments can be salvaged with humility and vulnerability.”

So I think the key is this: communication communication communication. Because everyone is vastly unique, multi-faceted and learning more about who they are and what they need every day, communication is key. Ask the hard questions of your people, and be comfortable with trial and error. Get it wrong the first time, but learn what to do better next time.

Don’t be afraid to pose the question to someone you’ve known for decades: “How can I care for you better?” I think the friendships and relationships we feel especially comfortable in should be the ones we resist “arriving at.” What a gift it is to know someone like the back of our hand but still recognize their depth, complexity, and proclivity to surprise us. And I believe that when we do that for others, we will watch it happen for ourselves. Friendships cannot be boiled down to a cheesy pop song, but even still — cheer loud, play hard, love well.

Photos by: Karen Marie Co.

Chantelle Gibbs

Chantelle is a curly-headed native of Los Angeles, with a love for puns, musical theatre, and lightly sweetened kettle corn. She currently works as an adjunct college professor of Communication and teaches art history at various elementary schools in Orange County. She is learning, slowly but surely, how to practice the art of seeing others and the world with whimsy and wonder.