Sugar’s twenties

Sugar’s twenties are presented not as a finished chapter but as a life that can be understood only in retrospect: marked by her mother’s death, uncertain relationships, heroin entanglement, and the labor of becoming a writer. In answering a twenty-two-year-old who asks what she would tell her younger self, Sugar turns remembered mistakes and ordinary days into advice without pretending that age makes the past simple or fully resolved. The decade’s defining movement is from self-judgment toward a more generous, still hard-won understanding of how a life takes shape.

A decade recalled from later life

Sugar’s account is framed by a reader who has followed her column and estimates, from its writing, that Sugar is in her early forties. The reader asks what advice she would give her twenty-something self; Sugar answers from a later vantage, drawing on remembered episodes rather than offering a single rule for success. The exchange makes the age difference part of the subject: the older voice can name consequences that the younger one could not yet see, but it does not claim that time eliminates uncertainty.

That retrospective voice belongs to a broader practice in Dear Sugar. Letters arrived through an anonymous form on The Rumpus or directly by email, and many writers did not know Sugar’s identity. The letters address love, grief, money, and family troubles; their selection is subjective, guided by what moves or challenges her. Sugar’s responses often bring personal memory to bear on a stranger’s difficulty. In this exchange, advice to a young reader becomes a way to arrange the decade’s incidents into a record of continuing change rather than a neat story of lessons learned once.

Work, ambition, and becoming

The decade’s creative life is described through work that could easily be mistaken for delay or failure. Sugar recalls waitressing, writing in her journal, taking long walks, and reading poetry, story collections, novels, and the diaries of people who had died. These activities did not look like a settled career, but she recasts them as part of her becoming. The point is not that every difficult day visibly advanced a professional plan; rather, a life was taking form while she was still unsure what it would amount to.

That distinction informs her counsel about writing. She tells her younger self not to confuse a life with a career: the work is to write, keep faith, and continue. She also imagines a book whose publication day the younger woman does not yet know. The future is therefore present as possibility, not as a promised timetable. This perspective connects with Sugar’s earlier experience creating the advice-column persona: she had imagined a woman with a troubled past and a reckless voice, but often found herself relying on wit when she could not reach the pain in a correspondent’s letter. After a year she quit. Her later reflections place value not in performing certainty, but in developing the capacity to meet difficult experience more honestly.

Family, grief, and the objects that remain

The most enduring memories of the decade gather around Sugar’s mother. At Christmas near the beginning of Sugar’s twenties, her mother gave her a warm coat she had saved for months to buy. Sugar responded by criticizing its length and puffiness and questioning whether it was too warm. Her mother died by spring. The coat became her last gift, and Sugar remembers regretting for the rest of her life what she had failed to say: thank you. The episode gives her retrospective advice its sharpest domestic detail: affection can be present in an ordinary exchange, while recognition of its importance comes too late to change the exchange itself.

A red dress preserves another part of that relationship. When Sugar said she did not have a dollar, her mother reached for the dress and bought it. Sugar put it in a box inside a cedar chest belonging to Sugar’s mother, carrying it through her twenties and into her thirties. After she had a son and then a daughter, the dress remained a secret among her mother’s things. When Sugar finally unearthed it, the object held together two facts that pull in opposite directions: Sugar’s mother had bought a dress for a granddaughter she would never know, and the dress had survived as a tangible connection between them. It makes family inheritance material and specific, without undoing the loss it records.

The loss of Sugar’s mother also shapes how Sugar speaks to other people’s grief. In a response to Living Dead Dad, whose son has died in a car crash, Sugar does not claim to know how a parent survives such a loss. Instead, she draws on her own continuing love for her mother, distinguishing grief from the ugliness of what caused it: the enduring pain is also evidence of enduring love. This later act of witnessing places the twenties inside a longer emotional history. The decade is not only a set of youthful errors; it includes a bereavement whose meaning returns in Sugar’s adult responses to strangers.

Risk, self-judgment, and small openings

Sugar’s recollections include decisions she later describes as mistakes, but her advice resists turning them into a verdict on the person who made them. She recalls becoming entangled with heroin and thinking of herself as worthless while riding a bus. A little girl boarded holding two purple balloons and offered Sugar one. Sugar refused because she believed she no longer had a right to such a small beautiful thing. In retrospect, she identifies that belief, not the child’s offer, as wrong. The scene concentrates the distance between feeling undeserving and being beyond kindness: the offer does not erase the larger difficulty, but it exposes the harshness of Sugar’s self-judgment.

Other counsel concerns intimacy and choice. Sugar tells her younger self that wanting to leave a relationship is sufficient reason to change its terms, even when love remains; leaving does not prove an inability to love. She remembers being invited to take ecstasy and advises declining, and recalls proceeding with an intimate encounter after learning there was no condom, an error for which she says she alone bore the consequences. These memories do not form a simple cautionary sequence in which every outcome was controllable. Instead, they show her identifying moments when a choice mattered while rejecting the idea that a person must remain in an unwanted relationship or define herself by a past mistake.

The shape of the advice

Sugar’s recollections resist the idea that childhood issues can be permanently settled in one effort. Work done in the twenties may need to be done again; understanding develops with age and years, especially around forgiveness. This recurrence gives the decade its structure: experience does not simply accumulate into mastery, because old questions return under new conditions. The younger self is not condemned for failing to know what only later life could teach.

Her advice also unsettles the demand to measure a life against a fixed image of adulthood. She asks the younger woman to stop treating the shape of her body as a problem, warns that assumptions about other people’s ease or wealth can reveal her own naïveté, and insists that love cannot be compelled. At the same time, she acknowledges that some struggles end in loss and that holding on is not always possible. Acceptance, in this account, is quiet rather than triumphant.

The result is neither a clean redemption story nor a catalogue of regrets. The coat, the boxed dress, the balloon offered on the bus, the journal, and the waitressing shifts give the period its concrete form; the advice gathers those details into a view of becoming as something made through ordinary labor, grief, misjudgment, and renewed attention. Sugar’s older voice does not promise that everything will turn out well. It offers something more measured: the past can be faced without making it the whole measure of the person who lived it.