This Is Probably The Greatest Advice Column Of All Time — And These Are The 15 Best Entries

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:

"Get comfortable being the man who says oh honey, I’m so sorry for your loss over and over again...

...I know saying those cliché and ordinary things makes you feel squirmy and lame. I feel that way too when I say such things to others who have lost someone they loved. We all do. It feels lame because we like to think we can solve things. It feels insufficient because there is nothing we can actually do to change what’s horribly true.

But compassion isn’t about solutions. It’s about giving all the love that you’ve got."

"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:

"It is not so incomprehensible as you pretend, sweet pea. Love is the feeling we have for those we care deeply about and hold in high regard. It can be light as the hug we give a friend or heavy as the sacrifices we make for our children. It can be romantic, platonic, familial, fleeting, everlasting, conditional, unconditional, imbued with sorrow, stoked by sex, sullied by abuse, amplified by kindness, twisted by betrayal, deepened by time, darkened by difficulty, leavened by generosity, nourished by humor and “loaded with promises and commitments” that we may or may not want or keep.

The best thing you can possibly do with your life is to tackle the motherfucking shit out of it. And, Johnny, on this front, I think you have some work to do."

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:

"You’re going to have to be brave. You’re going to have to walk into the darkest woods without a stick. You aren’t conventionally attractive or even, as you say, “normal-looking,” and as you know already, a lot of people will immediately X you out as a romantic partner for this reason. That’s okay. You don’t need those people. By stepping aside, they’ve done you a favor. Because what you’ve got left after the fools have departed are the old souls and the true hearts. Those are the uber-cool sparkle rocket mind blowers we’re after. Those are the people worthy of your love."

"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:

"So write, Elissa Bassist. Not like a girl. Not like a boy. Write like a motherf*cker."

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:

"I can’t say when you’ll get love or how you’ll find it or even promise that you will. I can only say you are worthy of it and that it’s never too much to ask for it and that it’s not crazy to fear you’ll never have it again, even though your fears are probably wrong. Love is our essential nutrient. Without it, life has little meaning. It’s the best thing we have to give and the most valuable thing we receive. It’s worthy of all the hullabaloo."

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:

"I have a lot of letters like yours. Most go on at length, describing all sorts of maddening situations and communications in bewildered detail, but in each there is the same tiny question at its core: can I convince the person about whom I’m crazy to be crazy about me?

The short answer is no.

The long answer is no."

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:

"A good place to start would be to let fall your notions about “perfect couples.” It’s really such an impossible thing to either perceive honestly in others or live up to when others believe it about us. It does nothing but box some people in and shut other people out and it ultimately makes just about everyone feel like shit. A perfect couple is a wholly private thing. No one but the two people in the perfect relationship know for certain whether they’re in one. Its only defining quality is that it’s composed of two people who feel perfectly right about sharing their lives with each other, even during the hard times."

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

"I hope you will be surprised and knowing at once. I hope you’ll always have love. I hope you’ll have days of ease and a good sense of humor. I hope one of you really will bake me a pie (banana cream, please). I hope when people ask what you’re going to do with your English and/or creative writing degree you’ll say: Continue my bookish examination of the contradictions and complexities of human motivation and desire; or maybe just: Carry it with me, as I do everything that matters. And then smile very serenely until they say oh."

"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:

"Real change happens on the level of the gesture. It’s one person doing one thing differently than he or she did before. It’s the man who opts not to invite his abusive mother to his wedding; the woman who decides to spend her Saturday mornings in a drawing class instead of scrubbing the toilets at home; the writer who won’t allow himself to be devoured by his envy; the parent who takes a deep breath instead of throwing a plate. It’s you and me standing naked before our lovers, even if it makes us feel kind of squirmy in a bad way when we do. The work is there. It’s our task. Doing it will give us strength and clarity. It will bring us closer to who we hope to be."

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:

"This is how you get unstuck, Stuck. You reach. Not so you can walk away from the daughter you loved, but so you can live the life that is yours—the one that includes the sad loss of your daughter, but is not arrested by it. The one that eventually leads you to a place in which you not only grieve her, but also feel lucky to have had the privilege of loving her. That place of true healing is a fierce place. It’s a giant place. It’s a place of monstrous beauty and endless dark and glimmering light. And you have to work really, really, really fucking hard to get there, but you can do it, honey. You’re a woman who can travel that far. I know it. Your ability to get there is evident to me in every word of your bright shining grief star of a letter."

"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:

"Contrary to what the Bachelor/Bachelorette television franchise and the entire spirit-decimating Hollywood Industrial Complex would have you believe, romantic love is not a competitive sport. Some of those women your boyfriend used to fuck have nicer asses than you. Some are smarter or funnier or fatter or more generous or more messed up than you. That’s okay. That has no bearing on you whatsoever. You’re not up against those women. You’re running your own race. We don’t dig or not dig people based on a comparison chart of body measurements and intellectual achievements and personality quirks. We dig them because we do. This guy—your lover, my anxious little peach? He digs you."

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."

"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:

"Forgiveness doesn’t just sit there like a pretty boy in a bar. Forgiveness is the old fat guy you have to haul up the hill. You have to say I am forgiven again and again until it becomes the story you believe about yourself. Every last one of us has the capacity to do that, you included, Desperate. I hope you will."

"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:

"You might, for example, be interested to know that the word prestigious is derived from the Latin praestigiae, which means conjuror’s tricks. Isn’t that interesting? This word that we use to mean honorable and esteemed has its beginnings in a word that has everything to do with illusion and deception and trickery. Does that mean anything to you, Awful Jealous Person? Because when I found that out, every tuning fork inside of me went hum. Could it be possible that the reason you feel like you swallowed a spoonful of battery acid every time someone else gets what you want is because a long time ago — way back in your own very beginnings — you were sold a bill of goods about the relationship between money and success, fame and authenticity, legitimacy and adulation?"

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:

"You will learn a lot from yourself if you stretch in the direction of goodness, of bigness, of kindness, of forgiveness, of emotional bravery. Be a warrior for love."

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:

"You cannot convince people to love you. This is an absolute rule. No one will ever give you love because you want him or her to give it. Real love moves freely in both directions. Don’t waste your time on anything else."