On losing my virginity
An honest conversation on the journey toward wholeness
Today I turn 29, and my singular wish is to live deliberately (shoutout Henry David Thoreau). I am not moving into the woods, but I am choosing to be more open in my writing.
As the great late Mary Oliver writes, “tell me about despair, yours, and I will tell you mine1”. I believe now is the opportunity to enter the void of shame with a lamp in hand and hope to bring others out of the caves I made my home in for so long.
So over the next few posts, I’ll be sharing openly around the topic of sexuality, spirituality, and my journey of finding healing in Christ, not only from but through the wounds and secrets I carried for a very long time2.
I hope that you, whoever and wherever you are, learn that on the other side of vulnerability and brokenness lies a grace, love, and acceptance that we all yearn for.
I’m still imperfect, and it has taken a great deal of time to heal. Though the words come from fresh scars, I hope you’ll learn, like I have, that God is our ever-present help.
Now let me tell you about the time I lost my virginity.
I lost my virginity at 19. I wasn’t in love; we weren’t even dating. It happened on the bench seat of my beloved used 1996 Toyota Tacoma. The exchange wasn’t beautiful or true; it was awkward and regretful and over sooner than it began.
I was about a month shy of moving to California to begin my second year of university. I never processed this moment, I just shuddered with shame, and like the rest of my belongings, packed my emotional baggage and spiritual pain in the back of my Tacoma and headed West.
Here I was, 19 and in Southern California. I was in a whole new world and in the heart of the Golden State. Pristine coastline, coffee, and gorgeous people everywhere.
It didn’t take long until I met an amazing Southern California girl. Kind and young and intelligent, we fell fast and hard. Sadly, our relationship imploded after 2 years because I cheated on her. A lot.
That’s how I found myself drowning in a sea of shame, 21 and on the couch of what would have been my future in-laws’ home, head in hands, sobbing and confessing about how I had just broken their youngest daughter’s heart.
I was crying, and I mean ugly crying, the type of crying when snot and tears flood out of every hole in your face uncontrollably.
In a moment of painfully awkward silence, Nancy, my ex’s mother, said something along the lines of: “Caleb, we forgive you, and God forgives you, but you need to figure out how you ended up here.”
This woman owed me nothing and had every right to curse at me, and yet her words punched the first hole in my armour of shame.
It would still take years to claw out of this ditch of destruction, but in that moment, this woman of God extended a hand.
I wish somebody had told me earlier that I was seeking God in my next orgasm. But as theologian AJ Swoboda, “searching for eternity in the orgasm always ends up disappointing us over the long run3.”
Two months later, I found myself in the office of a gifted psychologist. Now let me tell you about the beginning of my grand unfolding.
A Prayer from St Augustine for those with Longing Hearts:
Too late have I loved you, O Beauty so ancient, O Beauty so new.
Too late have I loved you! You were within me, but I was outside myself, and there I sought you!
In my weakness, I ran after the beauty of the things you have made.
You were with me, and I was not with you.
The things you have made kept me from you – the things which would have no being unless they existed in you!
You have called, you have cried, and you have pierced my deafness.
You have radiated forth, you have shined out brightly, and you have dispelled my blindness.
You have sent forth your fragrance, and I have breathed it in, and I long for you.
I have tasted you, and I hunger and thirst for you.
You have touched me, and I ardently desire your peace.
Mary Oliver, “Wild Geese,” in Dreamwork (Grove Press: London, 1986).
Lots of this I’ve processed in counselling and with trusted mentors and friends. If it brings up stuff in you, I hope that as I share my wounds, it might prompt you to reach out for help. As activist Bryan Stevenson said, “each of us is more than the worst thing we’ve ever done”.
A.J. Swoboda, The Gift of Thorns: Jesus, The Flesh, and the War of our Wants, (Grand Rapids: Zondervan, 2024).
Such beauty in uncovering hidden shame, I am always delighted to see how the Spirit redresses us.