8 Times Cheryl Strayed’s ‘Dear Sugar’ Column totally nailed Love and Life

In terms of life advice, the Dear Sugar section of Rumpus.com, a column once written anonymously by author Cheryl Strayed, was tough to beat.

I say ‘was’ because sadly, the column doesn’t exist anymore (it stopped in 2012). But luckily, its wisdom has been immortalized in the profound book, Tiny Beautiful Things: Advice on Love and Life from Someone Who’s Been There, a collection of the letters and responses from the column.

The letters and responses, mini-essays covering every sort of emotional problem, are stunningly full of truth and should probably be read by everyone of reading age.

Here’s eight times that Sugar totally nailed life and love.

What love is and when to say the words

Appeared in ‘Like an iron bell’.

This letter is from a dude who is plagued by the question of whether to tell his new girlfriend that he loves her. He has a twenty year failed marriage behind him, and associates love with ‘promises and commitments that are highly fragile and easily broken.’

Sugar tells him this:

“It is not so incomprehensible as you think, sweet pea. Love is the feeling we have for those we care deeply about and hold in high regard. The best thing you can possibly do with your life is tackle the motherfucking shit out of love.

“You aren’t afraid of love. You’re afraid of all the junk you yoked to love. And you’re convinced that withholding one tiny word from the woman you love will shield you from that junk.

“But it won’t. We are obligated to the people we care about and who we allow to care about us, whether we say we love them or not. Our main goal is to be forthright – to elucidate the nature of our affection when such elucidation would be meaningful or clarifying.”

How to deal with parents that don’t accept you as you are

Appeared in ‘That ecstatic parade’.

This letter is from a man who feels suffocated by his parents whom he lives with (he is 21). They know he is gay but will not acknowledge it. He won’t move out because he cannot pay for himself. Besides, he is reluctant to ‘run away’ from his problems.

Sugar tells him this:

“Figure out how to pay the rent. Your psychological well-being is more important than free access to a car.

“We are all entitled to our opinions and religious beliefs, but we are not entitled to make shit up and then use the shit we made up to oppress people. This is what your parents are doing to you. And by choosing to pretend you’re straight in order to placate them, you’re also doing it to yourself. You must stop.

“I encourage you to leave your parent’s home not so you can make some giant ‘I’m gay!’ pronouncement but so you can live your life with dignity among people who accept you while you sort out your relationship with them from an emotionally safe distance.”

How to deal with crushes when you’re married

Appeared in ‘A motorcycle with no one on it’.

This sweet letter is from a person that describes themselves as ‘crushed in middle age’ (a.k.a crushing on someone). They ask what they should do with ‘all the delightful but distressing energy’, given that they are married and cannot/will not act upon it.

Sugar says:

“You’re clear that you don’t want to act on that crush, so trust that clarity and be grateful for it. My inbox is jammed with letters from people who are not to clear. They’re tortured with indecision and guilt and lust. They love X but want to fuck Z. It is the plight of every monogamous person at one time or another. We all love X but want to fuck Z.

“Z is gleaming, so crystalline, so unlikely to bitch at you for neglecting to take out the recycling. Nobody has to haggle with Z. Z doesn’t wear a watch.

“Z is like a motorcycle with no one on it. Beautiful and going nowhere.”

On dealing with parents that get divorced in your adulthood

Appeared in ‘A new, more fractured light’.

This letter (not available online) is from a person asking how they can reconnect with their father in a genuine way, after he left their mother for a younger woman. They are furious and hurt and cannot look upon their dad in the same way.

Sugar instructs:

“Find a way to weave your father’s failing into the tapestry of your lifelong bond. Bravely explore what this new relationship means to him and ask where you fit into it. It’s going to be difficult but that’s no surprise. The story of human intimacy is one of constantly allowing ourselves to see those we love most deeply in a new, more fractured light.

“Look hard. Risk that.”

How to deal with losses of faith

Appeared in ‘The human scale’.

This powerful letter is from a woman whose 6 month old child has a tumor. She wants to know whether to attribute the successful surgery to God, after her faith hit a rock when her baby became ill.

Sugar sympathizes:

“Suffering is a part of life. I know that; you know that. I don’t know why we forget it when something truly awful happens to us, but we do.

“Countless people have been devastated for reasons that cannot be explained or justified in spiritual terms. To do as you are doing in asking ‘if there is a God, why would he let my little girl have to have the possibility of life threatening surgery’ – understandable as the question is – creates a false hierarchy of the blessed and the damned. To use our individual good and bad luck as a litmus test to determine whether or not God exists constructs an illogical dichotomy that reduces our capacity for true compassion.

“What you learned as you sat beside Emma in the intensive care unit is that your idea of God as a possible non existent spirit man, who may or may not hear your prayers, and may or may not swoop in to save your ass when the going gets rough, is a losing prospect.

“So it’s up to you to create a better one. A bigger one. Which is really, almost always, something smaller.”

On finding love when you aren’t ‘attractive’

Appeared in ‘Beauty and the beast’ .

This gut-wrenching letter is from a guy whose life is otherwise great, but who feels left out in the cold romantically, because of his disfigurement. He asks whether he should just close off that part of him.

Sugar says this:

“You say that people like you, but don’t consider you to be ‘a romantic option’. How do you know that? Have you ever asked anyone out on a date, or to kiss you, or to out his or her hands down your pants?

“I mean to inquire – without diminishing the absolute reality that many people will disregard you as a romantic possibility based solely on your appearance – about whether you’ve asked yourself if the biggest barrier between you and the hot monkey love that’s possible between you and the people who will – yes without question – be interested in you, is not your ugly exterior but your beautifully vulnerable interior.

“What do you need to do to convince yourself that someone might see you as a lover instead of a friend? How might you shut down your impulse to shut down?

“These questions are key to your ability to find love, sweet pea.”

On dealing with loneliness/desperation

Appeared in ‘The magic of wanting to be’.

This letter was from an aging single man desperate for love and scared to overwhelm the object of his affections, a colleague he met, with his needs.

Sugar tells him this:

“Your longing for love is just one part of you. I know that it feels gigantic when you’re all alone writing to me, or when you imagine going out on a date with a woman you desire.

“But don’t let them be the only thing you show. It will scare people off. It will misrepresent how much you have to offer. We have to be whole people to find whole love, even if we have to make it up for a while.

“It’s about the down in the dirt art of inhabiting the person you aspire to be, while carrying on your shoulders the uncertain and hungry man you are.”

On forgiving yourself for past transgressions

Appeared in ‘The bad things you did’.

This letter is from a person who used to steal a lot, and who no longer does but carries the guilt of his former ways. He asks whether disclosing the stealing would be helpful.

Sugar tells him this:

“The people you stole from don’t need you to ‘fess up. They need you to stop tormenting yourself over all those things you took that don’t much matter anymore. I’m not sure why you haven’t been able to do that so far, but I imagine it has something to do with the story you told yourself about yourself.

“The narratives we create in order to justify our actions and choices become in so many ways who we are. They are the things we say back to ourselves to explain our complicated lives. Perhaps the reason you’ve not been able to forgive yourself is that you’re still too invested in your self loathing.

“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.”

These are just my selection of the letters. There are a lot more in the book, which I wholeheartedly encourage you to read on the next duvet day.