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Content Warning: This section of the guide includes themes of cursing, parental neglect, and child abandonment.
Handler describes her early adult attempts to learn how to ski. One year, she and a man had a skiing date. She felt embarrassed and annoyed when he skied down a double black diamond ahead of her and criticized her for failing to get down the mountain. Not long later, Handler ended Chelsea Lately and spent four months in Whistler in British Columbia, Canada. She devoted her time to learning how to ski and soon began wintering in Whistler. In 2020, she bought a chalet here. Her managers advised against it, but she was determined, given the upcoming election and her desire to be happy.
Handler remembers her last session with Dan. She took his advice and listed the kind of man she’d want to be with post-therapy. She includes the list. The man would be emotionally strong, a skier, loyal, loving, and independent. Handler is glad she wrote the list even if she wasn’t looking for love then. Per Dan’s encouragement, she also decided to make a gratitude journal.
Handler describes her experiences during the winter of 2020. She wanted to spend the next lockdown in Whistler and secured a residency with Vogue Theatre in Vancouver to get her visa. Once in Canada, she quarantined with her dogs for two weeks per Canada’s guidelines. During this time, she read and journaled every day. She includes her 14 entries.
After quarantine, Handler started skiing every day. She woke up happy every morning. She still loves her Whistler house and is so thankful she has this place.
Handler recounts more of her experiences in Whistler. When she first bought her house, she didn’t know anyone in the area. Her friend connected her with a local named Donna. Handler didn’t want to ski with Donna because she’d been enjoying her alone time but made herself go. On the mountain, she met Donna and her friend Lucy, both of whom were in their sixties. Handler was surprised when the women treated her rudely and insisted Canadians didn’t want Handler there. Handler ignored their comments and skied with them. The women were competitive and condescended to her when she didn’t keep up. Then on one slope, Donna fell. Handler saw it as karma. At lunch, Handler decided not to eat with them and had a margarita at the bar alone instead.
Handler reflects on women like Donna and Lucy who put other women down. Her experience with them taught her about sisterhood and intolerance. At this point in her life she wouldn’t waste time with unkind people. In the following days, she hired a different woman to guide and teach her on the mountain.
Handler describes her friend from Whistler, Angela Shoniker, or Ange. Ange is a feisty, energetic, competitive athlete. She competes in all sorts of events and never stops moving. She also “has a temper” (108), which will go off if others are incompetent, slow, or lazy. Handler finds her outbursts funny but knows she’s strong, too. Last year, Ange saved a man from an avalanche. She reflects on how powerful Ange is.
Handler recalls one of her past relationships. She was dating a divorced man “with three daughters, ages eight, nine, and seventeen” (111). Both of their parents traveled for work and the eldest often cared for the younger two while they were gone. Handler wasn’t ready to meet them two months into the relationship, but the girls showed up at the boyfriend’s house unannounced on Valentine’s Day. Confused, Handler joked with the younger two who she began calling Whoopsie and Oopsie. She spoke to the eldest (who refers to as Poopsie) outside. Poopsie was upset because her dad promised to take her out but now he was bailing on her. Handler called the boyfriend and insisted he take Poopsie out while she stayed home with the younger girls. The boyfriend resisted but Handler didn’t give in. She was bothered by his behavior and told him the girls needed him.
The boyfriend tried to invest in the girls over the following days, but it didn’t last. Poopsie was particularly hurt by his disengagement. Meanwhile, Handler started seeing the girls regularly. A month later, the girls’ mom invited Handler on their family vacation. She worried her ex would work the whole time and the girls would misbehave if Handler wasn’t there. Handler’s friends warned her against going but she went for the girls.
Handler spent the majority of the vacation with Whoopsie and Oopsie. They joked that Handler was like a stepfather and started calling her Father. Handler fell in love with them. She is open about being child-free but she values her role in the girls’ lives.
The boyfriend spent more time with Poopsie in the following months. In the spring, he and Handler took her prom-dress shopping. Poopsie told Handler how grateful she was for her and admitted her dad’s last girlfriend had been jealous of her.
Handler reflects on her relationships with the girls. She always feels good investing in their lives. Their dynamic is rewarding and giving.
Handler and the boyfriend broke up not long later. Handler realized she loved the girls more than him. The boyfriend accused her of hurting the girls. Handler went to her therapist, who suggested she talk to Poopsie about the breakup, but not the younger two. Handler wrote Poopsie an email but never heard back.
A few weeks later, the girls’ mom contacted Handler, telling her how much the girls missed her. Handler’s friends didn’t think she should get involved with them again but Handler loved them. She started attending their games and concerts events and seeing them regularly. Meanwhile, she read parenting books. Then one night, Poopsie called Handler for help. Handler gave her a ride and let her sleep over. Handler never told her parents about this because she wanted to make her feel safe. She reflects more on these relationships. She cares about the girls’ lives because she cares about family.
Handler shares more about her relationships with the girls. She stayed in their lives over the next five years. Poopsie was in college but Handler saw Whoopsie and Oopsie consistently. Handler had a better dynamic with their dad now and one summer he asked her to take Whoopsie and Oopsie on vacation. Her friends advised against it, but Handler took the girls to her house in Mallorca anyway.
At 13 and 14, the girls often fought. The trip was difficult but Handler didn’t give up. Back at home, she started taking parenting classes. She read more parenting books, too. She showered the girls with love. Then one night, she took Whoopsie to a show. Backstage, Whoopsie showed Handler the playlist she made to feel calm. Handler was amazed, and wondered what other secret parts of her there were. In reflection, Handler asserts that while she’s child-free she is still a parent.
The anecdotes presented in Chapters 15-22 trace Handler’s work Finding Joy and Fulfillment in Personal Relationships. Handler frames this network of romantic and interpersonal experiences within the context of her time in Whistler. Whistler comes to symbolize Handler’s Pursuit of Authenticity and Personal Growth; this setting represents her private reality—a realm that is independent of her public image and offers her the space and calm to develop as an individual. Because Handler makes time to grow as a person, she is better able to invest in those around her. Over time, her self-reclamation begets her newfound devotion to cultivating lasting healthy connections.
The chapter “Looking for Love?” offers intimate insight into Handler’s outlook on love, romance, and intimacy. In much the same way that Handler describes the ideal woman she’d like to be in Chapter 1, in Chapter 16, she describes the ideal man she’d like to be in a relationship with. She is letting her reader into a vulnerable aspect of her internal world and her therapy work with Dan. Using a confessional tone, she admits that she “wasn’t sure that [she] was even the relationship type,” but decided to take Dan’s advice and describe “what a post-therapy relationship might look like for [her]” (85). This is an example of a personal growth exercise Handler completes along her journey toward authenticity. The exercise also chronologically precedes Handler’s subsequent descriptions of her relationships, including her bad skiing date, her uncomfortable skiing outing with Donna and Lucy, her musings on her friend Ange, and her foray into Poopsie, Whoopsie, and Oopsie’s lives. Handler is thus ordering her vignettes in a linear way to show how her internal work is directly impacting her interpersonal relationships. She begins to apply the things she learns in therapy to her interactions with others. For example, her decision to teach herself to ski after the bad skiing date captures her refusal to shape her life and sense of self around a man; she takes lessons to empower herself. Her decision to ski with Donna and Lucy despite her new introverted habits shows her desire to keep challenging herself socially. Her admiration for Ange exemplifies her refusal to condescend to other women and her insistence on surrounding herself with strong, positive energy. Finally, her investment in Poopsie, Whoopsie, and Oopsie conveys her discovery that she can be loving, parental, and giving while standing by her decision to remain child-free.
Handler’s relationship with Poopsie, Whoopsie, and Oopsie captures the essence of healthy, joyful, and fulfilling relationships. Handler is introduced to the three girls via her now ex-boyfriend. Although she thinks she’s falling in love with their father, Handler never lets her feelings for the boyfriend compromise her attention to the girls. Even when her friends and family warn her against getting too attached to the girls or letting their parents manipulate her, Handler stands up for what she believes in: showing love to those in need. In Chapters 20 and 21, Handler renders her experiences with the girls in vivid detail. These anecdotes have a cheerful, buoyant mood, but are also coupled with Handler’s more challenging bouts of reflection. The marriage of these tonal registers conveys Handler’s capacity for both joy and sincerity. Handler also describes her feelings for the girls and her decision to invest in their lives using assertive declarations:
I didn’t give a shit. I didn’t care if I was being manipulated by the parents. I loved these girls, and I wasn’t going to let the worry of potential future problems interrupt what joyfulness we were all experiencing in the present. The girls and I had bonded, and there was no going back (130).
Handler’s adamant tone captures her profound devotion to Poopsie, Whoopsie, and Oopsie. Furthermore, her devotion to the girls subtly conveys her personal growth. Handler has progressed in her personal growth journey to the point where she’s ready to make sacrifices for others, particularly innocent, loving individuals like the girls. Handler shares her de facto parenting stories on the page to further humanize herself and to illustrate how life-changing deep, selfless relationships can be. Such forms of intimacy aren’t limited to the romantic or sexual realm either.
Handler closes each of these chapters with grateful passages of reflection. She does so in order to share how her experiences are changing her and to offer self-help lessons to her reader. Her experiences, she suggests, are not anomalous; rather, they are examples of how rewarding life can be if one opens her arms to it.



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