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Content Warning: This section of the guide includes discussion of gender discrimination, sexual violence, and addiction.
Shields emailed Ali Wentworth in 2017 to ask if she could appear in an episode of Wentworth’s show, Nightcap. Shields loves performing in comedies, which she discovered after appearing in an episode of Friends in 1996. Wentworth responded happily, and the episode sparked a new, close, and unexpected midlife friendship: “One of the best things about making friends in this era, I’ve found is that those friends have only known you in this era. As much fun as shared history can be, sometimes it can also keep you stuck in the past” (127). Studies show that as we age, friendships are critical to our health. They even correlate to longer lifespans. Shields is “intentional” about her friendships now (129). She no longer feels obligated to befriend others and instead pursues friendships that are rewarding. Her female friendships are no longer characterized by jealousy or competition: “I no longer feel left out when my friends have other unique friendships or groups of friends with whom I am not as close” (131). Instead, her friendships are enriching. She does not have a core group of friends but “pockets” of diverse friendships that are fulfilling in different ways. Her perspective on and approach to friendship have changed with age and experience.
Shields dropped off her eldest daughter, Rowan, at Wake Forest University in 2021. She was surprised at the tears that arrived as she and her family drove away from campus. She and her daughters have always enjoyed spending time together, something that friends have noticed. While Shields knew that she had to let Rowan spread her wings, she also took pleasure in her daughter’s “pull” to return home: “You want them to love home, but you want them to be okay on their own. You want them to be independent, and yet there’s some delight when they still need you” (138). Shields’s mother ill-equipped her for life away from home, something she worked to avoid with her own children.
A new phase begins once one’s children leave home. Shields was already considering starting her business, Commence, before her first daughter went to college. She had more time to dedicate to her own interests once she became an empty nester. This phase brought “freedom of discovery […] [she could] now cater to [her]self” (141). The emptiness comes with mourning but also leaves space for new ventures. Shields states that one need not feel guilty if their entire life is not centered around their children. She made a point to work close to home when her girls were young because she knew that her time with them was limited: “[A]s much as work has always been a source of fulfillment for me, it has never given me the same pure joy that my family did” (147).
Research demonstrates that empty-nest parents find new fulfillment when their adult children become “social contacts” (147). Parental happiness increases as children grow up. Indeed, Shields admits that she and Rowan have developed a new friendship that did not exist when her daughter lived at home because she had to consistently parent her.
Shields no longer finds being alone scary. She takes pleasure in solitude, which she distinguishes from loneliness. She enjoys being with herself; one of her favorite new pastimes is enjoying a meal out with a good book or going to the theater alone: “It’s like riding in a car with someone and not feeling compelled to speak” (149). Though her children will always come home to visit, her relationship with them has permanently shifted in a new, positive way.
Shields had an unsettling encounter with a man during a social occasion in which he expressed his dismay that she was 58: “[T]he moment my actual age was brought up, his demeanor and the entire, previously comfortable exchange morphed. The fact that I, someone who he presumably remembers best as the pinup from his childhood, could be close to sixty, ruined something fundamental for him” (153). Shields condemns her objectification and the idea that her age is shameful. This interaction exemplifies how her experiences with men have changed with age. She is either treated with reverence because of her celebrity status or “invisible” (154). She refuses, however, to let the male gaze determine her value. The absence of the male gaze is an indication of how society sees an aging woman.
Sheilds says that male costars have often been difficult to work with because of their egos. They will correct her as if she is inexperienced, which is evidence of their insecurity. Men with highly successful careers do not display the same misogynistic disdain. She asserts that successful, confident women threaten men.
Shields met her husband, Chris, in 1999. They began dating after her divorce from Andre Agassi and married in the early 2000s. Some question how their marriage has survived for so long, but their relationship is not without its flaws; for example, she finds his teasing about her poor cooking skills irritating and has found ways to express her discomfort without an argument. She does not need her husband the same way she did when their children were young; the two must be intentional about spending time together. Divorce later in life has become more common as couples find that they are no longer compatible once their children have left home. The empty nest has forced Shields and her husband to “reexamine” their marriage. For example, Shields likes to go to bed early, while Chris enjoys late-night dinners out. She joins him on these outings occasionally because it is important that they socialize together. Chris, in return, spends time playing backgammon with her. Women’s sex drive decreases with age, and Shields finds sex painful sometimes because of the nonconsensual medical procedure that was performed on her, but she also acknowledges intimacy’s importance in maintaining a marriage’s health.
Shields ends the chapter by stating that she loves her family but also refuses to love them at the “expense” of her own happiness or well-being (168).
Shields’s youngest daughter, Grier, confronted her about never wearing or using many of her luxury items of clothing. This confrontation led Shields to ask what she was waiting for to “deserve” to wear them (170). She continues to work with her therapist to determine what childhood experiences led her to feel undeserving of enjoying what she earned. Her father wanted to protect her from the vanity of celebrity, so he frowned upon her wearing expensive clothes. So, she rarely spent the money she earned on herself as she grew up. When she later purchased designer items, she hid them away, not wanting to ruin them. She was determined to use them after turning 50. After Grier confronted her, asking why she owned nice things that she allowed to collect dust, Shields became even more determined to enjoy what she earned without concern for others’ perceptions: “It is a momentous shift when you start learning from your kids” (173).
Shields always wanted to be a mother. Her complicated relationship with her own mother, who had an alcohol addiction, shaped the way she reared her daughters. She frequently felt “skittish” as a child, constantly worried about her mother’s reactions to her (175). In contrast, she has parented her daughters so that they feel safe and have a stable family life. Shields always deferred to her mother’s opinions growing up. However, when Shields’s daughter was born, Shields realized that her mother knew little about children. Because Shields’s mother couldn’t dominate her granddaughters the way she had controlled Shields, her interactions with them were limited.
Shields’s conflicts with her children reached an apex when she entered menopause. They did not understand the hormone fluctuations that affected her mood. They were also entering womanhood during this time. Instead of shaming her daughters for their blossoming sexuality, like her mother did, Shields had open discussions with them so that they would not carry the shame she once did. In the Pretty Baby documentary, she reveals the story of a sexual assault, which she had not shared with her daughters. Grier was reduced to tears, and Shields realized that she should have discussed it with them first.
Shields enjoys this new phase of life in which her relationships with her daughters have grown stronger, despite them living away from home. They still call and visit frequently, and they feel comfortable discussing personal issues with her in a way that Shields never did with her own mother.
Getting older not only impacts one’s self-perception but also affects external relationships. These include relationships with one’s children, partner, and friends. Shields emphasizes Empowerment Through Aging as she writes about the newfound freedoms that come with getting older and the agency that this inspires in one’s personal and social life.
A key theme in this section is the idea that middle age does not have to be synonymous with stagnation. Her blossoming friendship with Ali Wentworth stands out as an example that counters this notion. Many women, by middle age, have an established circle of friends. According to Psychology Today, “[S]ome studies support the belief that making friends after retirement and even in midlife is more challenging. Earlier in life, school, college, and work provided ready-made social networks with all sorts of friendship possibilities. Older people often lack those natural networks” (Selig, Meg. “12 Ways to Make Friends in Mid-Life and Beyond.” Psychology Today, 7 Nov. 2022). Shields’s willingness to reach out to Wentworth for a professional collaboration led to a deep friendship, illustrating that confidence and initiative can yield unexpected rewards.
Another major topic explored is “empty nest syndrome.” According to Psychology Today, “Empty nest syndrome refers to the distress and other complicated emotions that parents often experience when their children leave home” (“Empty Nest Syndrome.” Psychology Today, 26 Feb. 2019). Shields again employs polemic reflection to acknowledge these feelings but counters that becoming an empty nester is also empowering because mothers have more time for themselves and their relationships. No longer engaging in the day-to-day work of parenting, she now finds time for solitude and pursuing new interests, including launching a business (and authoring this book). She has also reconnected with her spouse in a way that is not dependent on their mutual need for support while rearing children.
Perhaps most significantly, Shields’s relationships with her two daughters have changed in positive ways. While she fondly remembers their childhood, she also embraces the evolving dynamic of friendship and mutual learning that emerges as they grow older. For example, her daughter Grier’s criticism encouraged her to interrogate her own sense of self-worth and unlearn the self-criticism that her own mother instilled in her: “It was as if all my years of undermining my success and saving my stuff because I worried about what my mom would say just melted away. I felt like I had been given some sort of reprieve” (173). This moment represents a generational shift, where Shields has successfully fostered confidence in her daughters that she lacked in her own youth. In turn, her daughter’s insight has helped Shields address lingering issues of self-worth, demonstrating the reciprocal nature of their bond.
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