Sitting Alongside Heartbreak

Supporting friends through a polar vortex

Heartbreak feels like the most intense feeling I’ve ever experienced.
My reality with her is so much better than my reality without her. She added so much to my life.
I’m so sad.
I’m so alone. I don’t have anything anymore.
The most all-consuming black hole that I’ve ever been in, is having my heart broken.
I’ve lost her.
I go to work, then I drink, and then I come home to no one, and I sit and think about all the terrible things I’ve done.
And I’ve lost her all over again.
I can’t stop thinking about her because it’s all I have left of her.¹

During the holidays, a few of my closest friends confided that they were enduring heartbreak: dark nights of the soul marked by self-flogging and self-loathing, restless sleepless nights, minds caught in endless rumination whirlwinds. They teetered endlessly between victim and villain, trapped in that cruel internal seesaw, each swing deepening the torment of existential rejection and soul-eviscerating loneliness.

Whether the relationship ended in malice and meanness, through the exchange of cruel, unspoken resentment and contempt, or the connection simply withered away like a dying flower whose bloom was once so vibrant it seemed capable of defying time itself, the pain remains the same: undifferentiated, indivisible, offering no clear accounting of who suffered more.

As best I could, I let myself feel their sorrow, without taking on their suffering, and let my own emotions pour forth. Not from a performative place, but surrendering to whatever arose while resisting a deeper inner impulse to restrain vulnerability. There is in me an automatic, almost autoimmune instinct to regulate and contain my emotional experience, a force that lifts me out of the present and back into control.

It has taken me years to learn the discipline of simply sitting with people while they empty themselves of their inner turmoil. To meet their discomfort, their messiness, their brokenness, free from judgement, with grounded presence and embodied empathy.

Unless invited, I resist any urge to advise, to vilify or vindicate their exes, to project my own interpretations, or to insert my history as proof that I care.

I ask questions, some to bring clarity, others designed to dislodge something buried beneath words. I try not to step into the silences, leaving it for slow contemplation and meditation. I work to ensure my curiosity, anxiety, or discomfort does not disturb or disrupt.

I remember when these same friends stood where I now sit, consoling and bearing witness to my heartbreak during a season when the emptiness felt endless and hope appeared not merely absent, but extinguished forever. Those moments of total devastation when I couldn’t rise, when I confessed my mistakes, named injustices done to me, in the process of telling a fair yet honest story. When I spoke of love as something irrevocably denied, an entitlement granted to others, but forbidden to me.

I felt tremendous pride and gratitude in having cultivated close friendships that are mutually emotionally open and supportive. What brings me the most rewarding satisfaction is the knowledge that I changed. I chose courage over complacency, over fear. That in spite of my conditioning, I learned what it takes to be a good friend, in actions as well as words.

Men will do anything but cry. So men when you cry, you must fight the tears.²

At times, when real honesty was expressed harmoniously with raw emotions, I cried, not indulgent outpouring, but with eyes brimming and glassed over, as though commiseration were constrained behind an invisible pane. A silent benediction that says: I see you, I am here with you, you are not alone, and I feel the beauty in your heartbreak.

I want a great life. I want her to have a great life. She deserves that.
I put all my romanticism into that one night and I was never able to feel this again.
And my wife is sitting there looking at me, and I feel like I'm a million miles from her, and I know that there's something... wrong! You know, that I... that I can't keep living like this, that there's gotta be something more to love than commitment.
It made me feel cold, as if love wasn’t for me.
But then I think that...I might have given up...on the whole idea of romantic love.³

I loved her. I loved her so much.
And I ask her everyday why she did what she did. She took those with her when she went.
Leaving me… Angry. Empty. Confused.
And I know that hurt won’t ever go away. But there will come a day when I don’t feel it every minute. And the anger won’t feel so hot. And the other feelings will fade.
I’ll be left with only love.
A good friend once said to me, I can love you and still let you go.
So… I love you. And I let you go. I miss you.⁴

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Appendix

¹ -Diary of a CEO Clips, Steve Bartlett
-The Thunderbolts
-Castaway
-Wissking
² Men don’t cry, Michael Caine
³ Before Sunset, Richard Linklater
⁴ 13 Reasons Why