Cheryl Strayed and Mr. Sugar

Cheryl Strayed and Mr. Sugar’s relationship is marked less by effortless understanding than by their willingness to speak plainly when understanding fails. Across the book, their partnership appears in intimate conversations, shared work and childcare, and Mr. Sugar’s recognition that Cheryl Strayed’s grief for her mother remains part of her life. The relationship’s defining movement is from guessing what a partner wants toward asking, listening, and making room for what is true.

Meeting and Building a Partnership

Cheryl Strayed met the man who became her husband after a difficult stretch in which she had married while in college, divorced, and spent years concealing that she had not completed an English degree. His response to her unfinished education was direct: he encouraged her to finish, not because he wanted her to, but because he could tell that she wanted to. She initially thought he was being an asshole, and the two did not raise the subject again for a year. The exchange shows both the friction in their early communication and his ability to notice an ambition she had not acted on.

Their shared life is also presented as a practical arrangement between two working artists. When their children were four and six, Cheryl Strayed and Mr. Sugar were paying preschool tuition that had nearly bankrupted them. During the children’s infancy, they hired a part-time nanny for twenty hours a week at fifteen dollars an hour and divided the remaining childcare between themselves. When the nanny arrived, the couple worked in their shared basement office, each trying to get on with individual work while their children often settled down for a nap. Cheryl Strayed measured the expense against uncertain artistic earnings, wondering whether she had made enough to cover even one hour of care. The detail makes their partnership a matter of economic negotiation and daily labor, not simply affection.

Learning to Ask and Answer

An early sexual misunderstanding became a formative lesson in how the two approached intimacy. A few days into their relationship, Cheryl Strayed made a comment about desire and power that Mr. Sugar interpreted as a request for a particular kind of sexual behavior. He acted on that interpretation for a time, believing he was giving her something she wanted. When they eventually compared what they thought the other desired, they realized that neither wanted the activity they had been performing; each had been trying to satisfy the other through an assumption.

The discovery ended not in accusation but in laughter and a conversation about how the mistake had arisen. Cheryl Strayed told him what did not appeal to her, and he asked what did. She describes this exchange—questions followed by answers, and then questions in return—as the beginning of the way they proceeded together. Nearly fifteen years after the relationship began, she presents that practice as more durable than the intensity of their early attraction: they had to risk saying what was true about themselves, including truths that might feel embarrassing or unexpected. The episode offers a specific contrast between performing a guessed-at preference and building intimacy through explicit communication.

Years later, an object from the bathroom where the misunderstanding first took shape became a private emblem of that shared history. Before the couple moved out of the house, Mr. Sugar carefully peeled a Made in Argentina sticker from beneath the bathroom sink and made Cheryl Strayed a card with it. The sticker had outlasted the original setting, and he transformed it into a message for her. Its significance rests in the ordinary persistence of a place and an old joke-like reference: their relationship carries its beginnings forward without requiring the original room to remain.

Grief and the Continuing Place of Her Mother

Mr. Sugar’s partnership with Cheryl Strayed also includes her continuing grief after her mother’s death. In one account, Cheryl Strayed is thinking about how to answer a letter from Johnny. One evening she tells Mr. Sugar what is occupying her thoughts; they discuss Johnny’s troubles, after which Mr. Sugar turns off the light and falls asleep. Cheryl Strayed remains awake, thinking through her reply, then gets up, walks through the house, and sits at the kitchen table in the dark with a glass of water. Her cat joins her. The scene does not present Mr. Sugar as solving the correspondent’s problem or her own; it shows that she can bring the question into their shared life, even as the work of composing an answer continues alone.

Her mother’s absence is not treated as a sorrow that marriage or family life has erased. Cheryl Strayed recalls that her mother’s final word to her was love, spoken when she was too ill to manage a fuller phrase. She also describes the lasting pain of not being present when her mother died and the final moments that remain fixed in memory. In another reflection, a jar of stones her mother had kept briefly gives Cheryl Strayed the sensation of holding her, before she recognizes that no object can restore her. These memories clarify what support from a spouse means in the book: not undoing the death, but living alongside a grief whose reality persists.

When Cheryl Strayed urges a bereaved man to make room in his life for his fiancée’s dead mother, she identifies Mr. Sugar as someone who has done this for her. She also names friends and acquaintances as sources of similar care, so the evidence does not make him the only person who has helped. Rather, his place in her account is that of a husband who acknowledges the continuing significance of a loss. The mother remains part of Cheryl Strayed’s emotional life, and their marriage can recognize that presence instead of demanding that grief be finished.

Shared Life and Mutual Recognition

The book connects their private bond to the larger demands of work and parenting. Cheryl Strayed recalls how she and Mr. Sugar tried to balance making a living, caring for young children, and paying for help; the costs could exceed what her artistic work brought in. She also describes the affection and attention in their household through small episodes, including telling him about the letter she was trying to answer and sharing the fact that she was thinking about someone else’s distress. Their partnership is thus shown as a setting where individual work and responsibility for others continually meet.

Taken together, the episodes describe a relationship sustained by repeated acts of recognition. Mr. Sugar notices that Cheryl Strayed wants to complete her degree; they learn to ask rather than infer what the other wants; they share the financial and caregiving strain of raising children; and he makes room for her mother’s enduring importance. None of these gestures abolishes uncertainty, economic pressure, or bereavement. Their significance is that the couple’s life is not built on pretending those difficulties have disappeared. It is built on acknowledging them and continuing to make a shared life around what remains true.