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When asked for general advice for people in their twenties, Strayed offers that they should be “ten times more magnanimous” than they believe themselves capable of being (147). This is because people in this decade of life tend to lack humility while being insecure at the same time. However, they will grow and develop self-knowledge if they move toward generosity.
A 26-year-old man calls himself Beast because a rare blood disorder has affected his physical development. While he has managed to have a full enough life, he does not consider himself a romantic prospect for anyone and so shuts himself off from this part of life. He wants Sugar to tell him whether it is better to give up on love and concentrate on the parts of his life that are thriving.
Sugar tells him about her friend, a gay man she calls Ian, who was face was physically affected by burns when his kitchen blew up when he was 25. While Ian allowed himself to thrive and take risks with business and friendship, he unequivocally excluded himself from the romantic arena. When he died by suicide at age 44, Sugar intuited that this was because he had shut himself off from romantic love and not because he had been burned in the first place.
Sugar thus feels that Beast’s real question is not about whether someone will ever love him but about whether he is capable of keeping the possibility open for himself. She is adamant that while there are many who will reject him on superficial grounds, there are others who will see the extraordinary person he is inside and fall in love with him.
A woman called Over It wonders whether she should tell her current boyfriend about a sexual assault that happened when she was 17. While she says that it does not affect her day to day, it was a formative experience that shaped who she is.
Sugar salutes the woman for not letting what happened to her define her, as “something ugly happened to [her] and [she] didn’t let it make [her] ugly” (159). She advocates that Over It tell her boyfriend, as withholding the trauma magnifies the secret and gives it power.
A woman who calls herself Crowded complains that her two adult sons have moved back into the family home, unasked, in the wake of her ex-husband’s (their father’s) death. While she is sympathetic to her sons’ plight, she finds them sloppy and unmotivated and suffers from having no space for her personal lifestyle choices. She asks Sugar’s advice in getting these two grown men to leave her.
Sugar shares a story of being too afraid to swim by herself during her childhood swimming lessons at the YMCA. It was only when her mother entered the water with her and spontaneously let go of her hands that Sugar discovered she could swim on her own and made it to the other side of the pool. She advocates that Crowded needs to “fling [her] sons away from [her] so they can learn how to swim” (163). Their problem is that they have not fundamentally separated from their mother and so take her needs for granted.
Three women—Playing It Safe, Standing Still, and Claustrophobic—write to Sugar with a variation on the same question: Should they leave a stifling but secure relationship to go and explore who they really are?
Sugar answers their letters together because “placed alongside each other […] they tell a story complete enough that they answer themselves” (169). She experienced the same issues when she was married to a man she loved and wanted to leave at the same time. She advocates that despite their partners’ virtues, the women should end their relationships because “wanting to leave is enough” (171). She reminds them that women especially feel pressured to put others’ needs before their own; however, leaving their partners and decency aren’t mutually exclusive, and they have an ethical responsibility to be honest. In the long term, this will be an act of kindness toward their partners.
A woman who calls herself Man Juggler is opening herself up to the experience of nonmonogamous sex and enjoying it, although she feels overwhelmed with having to juggle different men. After sleeping with three men on successive nights, she wants Sugar’s advice on whether she needs to tell each of the men what she is up to.
Sugar says that it is absolutely Man Juggler’s responsibility to tell her partners that she is sleeping with other men. She should also acquire new partners at her own pace and not be afraid of the “negative space” between conquests, so that she can appreciate what she is getting (177).
A middle-aged woman called Wanting wants Sugar’s advice about entering a sexual relationship after the end of her marriage. She worries that her age and drooping body will disqualify her from the physical intimacy she desires and wonders how to be naked in front of a new man who may prefer a firmer, younger woman.
Sugar advocates that Wanting’s insecurities are common among women, including herself. She encourages Wanting to embrace her middle-aged body and give herself license to have the sexual experiences that she wants in it, despite the dominant culture’s messages. She says that being honest about her insecurities with her partners will put them both at ease, as they will likely be laden with their own.
For nine months, Needs Direction has been dating a guy whom she adores but who will not commit to an exclusive relationship with her. She is now attempting to be friends with him but wonders whether keeping him in her life is unnecessary torture.
Sugar advocates that there is nothing the woman can do to change the man’s feelings about her and make him want a committed relationship. She would be best served giving him up completely, as staying with a partner who does not love her is an entirely optional form of torture.
Daughter with (Maybe) Expired Daddy Issues is a 30-year-old woman who has made a break from her dysfunctional childhood to set up a new life in Europe. Her fiancé, however, has suggested that the woman’s father be in their wedding, despite an estrangement owing to the latter’s drunk and stoned behavior. She is conflicted as to whether to invite her father to be part of her big day.
Sugar advocates setting boundaries: The woman should be firm about the fact that she does not want her father to be in the wedding. She points out that she ought to be honest to her fiancé about why they should not invite her father and that it should ultimately be her decision. Instead, she should consider being honest with her father about her decision to leave him out of the wedding. Sugar notes that if he is a decent human being, he will respect her choice and seek to mend the error of his ways.
Haunted by His Sexual Past has met a wonderful man but is disturbed by frank stories of his sexual past, which include an orgy. She is now beset by jealous insecurities, thinking that she may not be enough for her partner.
Sugar advises that the letter writer herself is her own problem, as she is haunted by “[her] own irrational, insecure, jealous feelings” and risks pushing her boyfriend away (194). In contrast to what popular culture makes us believe, Sugar notes, the woman is not in competition with her boyfriend’s many partners, because in this moment, he has chosen her. Sugar had to learn this lesson herself when discovering an old photograph of Mr. Sugar’s dancer-bodied ex in the basement. After having a conversation, they were able to laugh about it. She advocates that the woman should learn from this example, embrace her lover’s intimate chat about his exes, and use it as an opportunity to grow closer to him.
Wearing Thin, a 25-year-old ex-student, is obsessed with her student-loan debt and resentful of her parents for not helping her with this and further supporting her by paying for a graduate degree. She feels that this issue has eroded their relationship, as all their conversations are now about student loans.
Sugar shares that her parents did not fund any of her education and that she had to do so herself through a chain of continuous jobs. She still, at the age of 43, has student-loan debt to pay off. However, this has far from ruined her life or prevented her from indulging in expenses such as expensive preschools for her children or organic shampoo. There were times, however, when Sugar, who wanted to be a writer and thought she needed glamorous experiences such as European trips and internships at magazines, felt resentful of more affluent students. In the long term, her many diverse employments also provided a bigger-picture environment and contributed to her education.
She states that Wearing Thin needs to stop feeling sorry for herself, embrace the cards she has been dealt, and fund her own way through her dreams, even if that means taking out more loans. This will finally liberate Wearing Thin’s relationship with her parents from the preoccupation of financial obligation.
A man who calls himself Gump is confused by the behavior of his “self-absorbed crazy” ex-friend of his ex-girlfriend, the former of whom he had a sexual relationship with for a fortnight (209). After this point of connection, the ex-girlfriend’s ex-friend broke it off with him to announce that she was engaged. He feels that he really connected with this woman and wonders what he should do.
Although she notes that she is a staunch anti-Republican, Sugar quotes Donald Rumsfeld’s distinction between the known and unknown elements of a situation. She concludes that while much of the ex-girlfriend’s ex-friend’s motivations are a mystery, “[he has] nothing for these women […] these women have nothing for [him]” (210).
Orphan, a 28-year-old transgender man, was disowned by his parents after telling them that he intended to have a gender confirmation surgery. He made a happy life in a new town, living as a man, and feels that he has “created an island far away and safe from [his] past” (212). However, seven years later, his parents got in touch to apologize for their initial response and to ask to be part of his life. He wonders whether to take them back.
Sugar tells Orphan that he should forgive his parents for his own sake and that refusing to accept them after their significant change in view “isn’t all that different from them refusing to accept you for who you are” (213). Instead, he should welcome them now that they have seen the light.
Bodies are a dominant issue in Part 3, as correspondents’ letters showcase the vulnerability associated with physical appearance and the defenses people put up to shield themselves from rejection by others. This is especially the case with the young man with physical differences who calls himself Beast, the middle-aged woman who fears that no one will want to be intimate with her because she has lost her nubile charms, and the transgender man who fears letting his remorseful, once-prejudiced parents back into his life. Sugar, who remains a champion of human connection, affirms that despite their insecurities, these correspondents must risk rejection and disappointment because love is what makes life worth living. She employs radical empathy and shared pain when she tells the middle-aged woman that she shares her insecurities and advocates that they “have to be as fearless about [their] bellies as [they] are with [their] hearts” (181), thereby affirming that every body is deserving of love, attention, and pleasure, regardless of whether it conforms to what a patriarchal society finds attractive. Sugar dispenses the vision of holding this truth in their hearts, even as they accept that many people will reject them from the outset. She thus encourages the correspondents looking for love to embrace this paradox, while advocating that the transgender man does not shut himself off from the renewal of his parents’ love, even as their former rejection of him will always hurt. Notably, the acceptance of one’s nonconventional body runs alongside making peace with the imperfection and unpredictability of love. While Sugar acknowledges that the media categorizes bodies by their lovability, she says that it is up to her correspondents to decide if they are capable of letting the type of love they are craving in.
A new format to correspondence is introduced in this section, in “The Truth That Lives There,” as Sugar addresses three women in unhappy relationships. While Sugar’s usual policy in her columns is Advice for Individuals, Free from Identity Politics, here, she overlooks the particulars that differentiate the women—religious or secular; married or cohabiting; partnered with someone their age or older—to address their common predicament of wanting to leave a man they love. The “Truth” that Sugar refers to in the title of this column can be found in the women’s consideration of stories that are similar to their own, including Sugar’s. This will divest them of the shame of feeling uniquely culpable in the situation of wanting to leave someone who has been good to them—and also bring home the stark truth of their own feelings by seeing them reflected in others. Here, Sugar performs the work of radical empathy and shared pain on an implicit level, as well as adopting rhetoric that creates a momentum of its own in the mantric repetition of the word “go” (170).
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