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In concert with the title of her book, Sugar’s columns are peppered with references to small, everyday things that can nevertheless change a person’s attitude or even the course of their lifetime. The motif of tiny beautiful things appears most explicitly in Strayed’s advice to her younger self, when she was dealing with drug addiction and felt too valueless to deserve the simple purple-balloon gift offered to her by a little girl. While the younger Strayed felt unworthy of such a gesture, Sugar advises her that she still has the “right to such tiny beautiful things” regardless of what she has done (352). This shares the message that all people are worthy of redemption and a second chance, as well as that some of the joys and distinctions in life emerge from small-scale objects and events rather than the grand ones society traditionally values.
Strayed demonstrates the potential profoundness of tiny, beautiful things in the image of the yard-sale toddler dress her mother picked up for her when Strayed was uncertain she wanted to have children. Still, she was drawn to the precious object, quaintly sentimental in its red velvet with a white lace collar. While Strayed’s mother was able to acknowledge the dress as “the sweetest thing” and intuited that Strayed should have it (321), Strayed was initially dismissive. However, the tiny one-dollar investment amounted to more than she could have ever imagined when the impossible feat of a long-dead grandmother buying a dress for a granddaughter she would never see came to pass. Sugar comments on this, observing “how little” and [h]ow big” the event was, and concludes that “the red dress was the material evidence of my loss, but also of the way my mother’s love had carried me forth beyond her, her life extending into my own in ways I could have never imagined” (323). Ultimately, Sugar recommends cherishing the small things, because they might have an outsized bearing on one’s future.
Smallness also occurs in the “small thing” of writing a letter in the face of someone’s pain, which is exactly the work of Dear Sugar (354). While a letter cannot change someone’s circumstances, it can offer compassion and companionship. Sugar also draws upon this idea in her advice to Abbie, the mother of a baby with a brain tumor who wonders about the existence of God. Rather than contemplating the role of heavenly magnitude in human affairs, Sugar references the more diminutive “human scale” of assistance, in the form of compassionate wishes (146). While this seems paltry compared to Abbie’s notions of a supernatural God who can right wrongs on a whim, Sugar attests to the human scale providing a grace that can help people get through even the worst circumstances.
Loss is a constant motif throughout the columns and appears in a different guise in every letter. Sometimes the correspondent’s loss is an obvious one that has already occurred—for example, in the form of bereavement or estrangement. Sugar, who lost her mother prematurely, especially empathizes with correspondents with similar experiences, and her first piece of advice is always to accept that the loss happened and that it was cataclysmic. For example, in the reply to Bewildered, the man who wants to help his fiancée get over her mother’s death, Sugar quotes a middle-aged friend who lost her mother in adolescence and told her that “it will never be okay that [their] mothers are dead” (97). She points out that the fiancée’s every experience after the death was “informed and altered by the fact that she lost the most essential, elemental, primal, and central person in her life too soon” and therefore there will be a part of her that will never be OK (98). Here, Strayed’s list of adjectives brings home the nurturing impact that a mother has on a person’s youth, thus drawing attention to the pain of its absence. At the same time, Sugar encourages all bereaved people to accept the paradox that their life can go on and be fruitful, although part of them will always be frozen in grief.
Other forms of loss in the columns are more hypothetical. This is especially evident with correspondents who want to leave a relationship because they can imagine something better but are afraid of letting go of a good partner in case they never find another. However, they know that staying in the relationship would mean loss of one’s true self, as one woman asks, “[D]o I […] rub myself out until maybe I am the person I was always expected to be?” (168). Sugar, who also made the difficult decision to leave a husband she loved, advocates in favor of preserving one’s truth and losing the other. She affirms that the uncertainty of the future with its potential losses is a fact of life that all must accept; however, it is also in one’s own power to plant seeds for good things that can replace the loss.
Tough love is a frequent motif in Sugar’s columns, as she favors telling correspondents what they need to hear to grow, both as individuals and in relationships, instead of spouting platitudes that will placate them. Sugar, who is aware that a person’s twenties are their most self-absorbed decade, in which they are both insecure and arrogant, is especially strict with those who display youthful entitlement. For example, she tells Wearing Thin, a young woman who is angry with her parents for not funding the graduate degree that she believes will be the ticket to her dream job, that it is her own attitude that needs mending. Rather than blaming her parents for her financial predicament and lack of graduate degree, Wearing Thin needs to grow up and take responsibility for doing her life herself. She tells Wearing Thin that her notion of being defined by student loans is a “threadbare cape [she’s] wrapped around [her]self composed of self-pitying half-truth” that will keep her stuck (202). She offers the perspective that Wearing Thin can follow her own example and work to pay off student loans while living her life abundantly and reaching toward her dreams. Ten years later, in Sugar’s Substack advice to Twenty-Five, the young woman who is wasting her life instead of going for her dreams, Sugar reinforces her message to Wearing Thin by stating that real life starts when one gets out of one’s comfort zone. While Sugar’s family-of-origin poverty meant that she was forced into independence and self-reliance from a young age, she often dispenses this hardship as a cure for young people who are still clinging to the parental nest.
On the other hand, the motif of tough love is prevalent in Sugar’s advice that people should maintain boundaries with relatives who are abusing or exploiting them. Sugar offers us the other perspective on Wearing Thin’s type of problem in “The Other Side of the Pool,” where a mother is desperate to get her adult sons to leave her house so that she can have the independent existence she dreams of. Using the story of her own mother’s sudden letting go of her in the swimming pool as a metaphor, Sugar shows that children—whether young or adult—will only flourish independently when you demand it of them. She tells this mother in no uncertain terms that she “need[s] to fling [her] sons away from [her] so they can learn to swim” and simply tell them to move out (163). By resorting to this tough love, the mother will enable her sons to realize their potential as adults, and the whole family will benefit by moving on from this regressed state of development.
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