The 15 Best 'Dear Sugar' Columns To Read When You Need A Dose Of Compassion & Inspiration

Everyone has their own road to Cheryl Strayed. I first read Tiny Beautiful Things, a collection of "Dear Sugar" columns, when a friend sent me a copy a few months after the death of my mother. One essay in particular — "The Black Arc Of It" — became my guiding light through the darkest periods of my grief. I've read it dozens of times since then, and I've shared it with nearly all of my friends and romantic partners. It's an essay that has guided, shaped, and informed my life as a motherless daughter. Since then, her other essays have provided comfort when I was lost in relationships, lost in my writing, or lost in myself.

For the uninitiated, here's the story behind "Dear Sugar": for years, Cheryl Strayed anonymously responded to advice seekers under the pseudonym "Sugar" in a column for The Rumpus. She eventually revealed her identity, and the column took its final bow in written form. "Dear Sugar" now lives on as a podcast co-hosted by Strayed and the column's original writer, Steve Almond.

But the sage, compassionate, and sincere words of wisdom she shared over the years are still available online and in book form, as Tiny Beautiful Things.

Tiny Beautiful Things by Cheryl Strayed, $10.28, Amazon

Before you head to the bookstore to pick up your copy, here are the 15 "Dear Sugar" columns I return to again and again — and my favorite nuggets of advice from each one:

"The Black Arc Of It"


It's clear "Bewildered" is authentically and generously in love with his fiancé — so much so that he wants to know how to better address her ongoing grief, in the wake of her mother's death. In "The Black Arc Of It," Sugar writes:

"Like An Iron Bell"


"Johnny" believes he's in love with the woman he's dating. He thinks she might be in love with him, too. But they both have baggage from past relationships. Should he tell her he loves her? What the hell is love anyway? In "Like An Iron Bell," Sugar writes:

"Beauty And The Beast"


A 26-year-old man who signs his letter "Beast with a Limp" describes himself as "incredibly ugly." He writes that he was born with a rare blood disorder that has left him with physical deformities and joint abnormalities. He wants to know: Should he keep trying to find love? Or should he give up on the idea entirely? In "Beauty and the Beast," Sugar writes:

"Write Like A Motherf*cker"


"Elissa Bassist" is afraid she writes like a girl. She tells Sugar that she's depressed, but doesn't have a bad life and didn't have a bad childhood. She writes that she's jealous, she's insecure, and above all, she's worried that she will never write anything worth reading. How can she be the writer she wants to be? In "Write Like A Motherf*cker," Sugar writes:

"The Magic Of Wanting To Be"


A 64-year-old man is single and wants to find love. More specifically, he wants to ask out a younger woman he met while volunteering, but he's afraid — afraid she might say no, afraid she might say yes, afraid he might never fall in love again. In "The Magic Of Wanting To Be," Sugar writes:

"A Motorcycle With No One On It"


This particular "essay" is actually a combination of five different letters and responses. In my favorite of the five, "Needs Direction" writes to Sugar about the man they've been seeing for a year who just won't commit to them. Should they stay — or go? In "A Motorcycle With No One On It," Sugar writes:

"A Bit Of Sully In Your Sweet"


Soon-to-be wedded "Happily Ever After" wants to know if the "perfect couple" actually exists or if marriage is ultimately a doomed endeavor. In "A Bit Of Sully In Your Sweet," Sugar writes:

"The Future Has An Ancient Heart"


A professor asks Sugar to deliver a "graduation speech" to her creative writing students. In "The Future Has An Ancient Heart," Sugar delivers:

"Tiny Revolutions"


"Wanting" is a 50-something woman who is separating from her husband after years of a lonely marriage. She wants help with a two things: creating more loving relationships in her life and accepting her body. In "Tiny Revolutions," Sugar writes:

"How You Get Unstuck"


In one of the most heartbreaking "Dear Sugar" letters of all time, "Stuck" asks how she can move past her grief over the miscarriage of her daughter. In "How You Get Unstuck," Sugar writes:

"Romantic Love Is Not A Competitive Sport"


"Haunted By His Sexual Past" is dating a wonderful man, but she struggles with his openness about his sexual history. She wants to know how to stop comparing herself to the lovers of his past who she's convinced are prettier, more adventurous, better in bed, and funnier than she is. In "Romantic Love Is Not A Competitive Sport," Sugar writes:

Later, she writes one of the most famous "Dear Sugar" lines of all time, the one that's splashed across the cover of the book: "Let yourself be gutted. Let it open you. Start there."

"The Bad Things You Did"


"Desperate" has done some things they're not proud of in the past, and they don't know how to forgive themselves and move forward. In "The Bad Things You Did," Sugar writes:

"We Are All Savages Inside"


"Awful Jealous Person" is... well, jealous of all her writer friends (and not-friends and enemies) who are more successful than she is. She went to a prestigious college. She thinks she should have made it by now. In "We Are All Savages Inside," Sugar writes:

"Be A Warrior For Love"


This isn't a column, but a series of quick-fire answers to short questions Sugar received via DM. In "Be A Warrior For Love," she writes:

"Tiny Beautiful Things"


Of course, this list wouldn't be complete without Sugar's Magnum Opus: "Tiny Beautiful Things." It is not my personal favorite, but it does nicely sum up the truth that lies at the heart of every "Dear Sugar" column: You deserve tiny beautiful things. "Seeking Wisdom" asks what Sugar would tell her 20-something self, and she writes, among other things: