Some days, friendship feels light, uplifting and fun. But other days, friendship feels heavy, burdensome and uncomfortable, when we reveal truths the relationship compels us to share. This is the more difficult side of what theologian L. Gregory Jones calls holy friendship.

“Holy friends challenge the sins we have come to love, affirm the gifts we are afraid to claim and help us dream dreams we otherwise would not dream,” Jones writes.

The conversations of holy friendship that affirm our gifts and help us dream dreams are often welcome and uplifting, pointing to a hopeful, beautiful future. But those that challenge the sins we have come to love are most often not; they get into our personal business and habits, threatening the places where we are comfortable and would rather be left alone.

Sin holds us back from embracing God’s call to live into a better, holier future. This includes things we have done or have failed to do, as well as things that others have done to us or have failed to do for us. It also includes broader systemic and historical dynamics that make it difficult for us to see ourselves, our communities and our institutions -- and even God -- clearly.

Holy friends help us recognize our patterns of self-deception, learn new, more faithful habits and discover forgiveness. This is especially important for those comfortable sins that have become so much a part of us that we have found ways to characterize them as not so bad, or even somehow good.

Challenging the sins we have come to love requires significant trust and emotional intelligence, which is why holy friendships develop over time and through shared experiences.

For younger adults, holy friends may be college classmates with a history of learning and living together. For midlife adults, they may be the people we raise our kids alongside, sharing the challenges and blessings of parenthood. For many clergy, they are the seminary classmates who remind us of the early joy and enthusiasm we had for ministry and can recall with us stories of vocational discernment, enduring Greek and Hebrew, and learning how to “become” ministers.

Because they have spent time with us, know our personalities and limits, and care about our growth and development, holy friends can sense when the time is right to initiate challenging conversations. Trust, empathy and clarity of intention are foundational to such critical conversations.

The year I was writing my dissertation, my spouse took our kids away for spring break -- a gift of six uninterrupted days for an all-out writing sprint. My family was excited about what I would accomplish while they were gone, but the silence quickly became overwhelming for me. I began looking around the house for projects. Pinterest became my best friend and worst enemy. I hung ridiculously trendy shelves in the mudroom and wallpapered the back wall of the pantry. The back wall. Of the pantry.

Midway through my “writing sprint,” I had a scheduled video call with my classmates to check in about our progress. I proudly took my peers on a visual tour of my home improvements, glowing in the oohs and aahs some of them offered.

And then my friend Chris chimed in.

“Victoria, stop it,” he said. “You have been given an incredible gift of time, quiet and dedicated space to write, and you are totally blowing it. What are you thinking? You need to sit down, get off the internet and write.”

At first, I was a little hurt; his words stung. The pantry was beautiful, and the shelves were totally on-trend. But he was right. My spouse and children were giving me a generous gift, and I was abusing it. Chris named my sin and helped me see how my actions were hurting my family and me. It was rare for Chris to speak to me like this, which got my attention all the more. We usually affirmed and encouraged one another, exchanged ideas and laughed together. That foundation of positive interactions, respect, trust and investment in one another enabled Chris to be a holy friend -- and enabled me to hear and accept the truth he offered.

Because of the deep love present in holy friendships, we can name and challenge sins, because we know we are all tethered to our fallen nature. While acquaintances may know us in a particular light, holy friends know the good, the bad and the ugly. These friendships aren’t always fun, because they are often marked by hard conversations and accountability. This is why it is easy to collect “friends” on social media and much harder to find or be an embodied holy friend.

The forward-looking, life-giving energy that we discover in these relationships is rooted in and points us toward a sense of blessing and hope that comes to us as a gift from God.