Is She Really Going Out with Him?

Will Havers is the male deuteragonist and Anna’s love interest. At first, Anna perceives Will as an arrogant flirt gaming to take over her column. She says, “He reminds me of a cartoon villain or the man on the cover of a romance novel. His good looks are so boringly predictable, it’s all 2D perfection, there’s no nuance to his face at all” (19). Though handsome, Will is eight years younger than Anna, a co-worker and, in her mind, not a romantic possibility. As Anna embarks on her structured dating experiment, Will serves as a counterpoint to the men she meets through arranged outings. While she seeks love offline, Will uses dating apps. However, their collaboration creates forced proximity, and Will’s refusal to fit into her meticulously crafted experiment frustrates her, making him feel like an antagonist to her mission. Will and Anna embody the enemies-to-lovers trope as their interactions are charged with a push-and-pull dynamic. While they enjoy each other’s company, Anna feels like Will is imposing on her professionally at a time when she doesn’t need any more friction in her life. Eventually, Anna learns that Will’s pestering and provocation result from his long-standing crush on her.

While many of her dates feel transactional or artificial, Will’s presence feels natural and unscripted. Every date highlights the shortcomings of seeking structured, quantifiable experiences rather than allowing for organic connection. On their trip to the Hay, Will transforms from enemy to friend as it becomes clear that Will is not malicious. Rather, his ambition stems from deeper emotional wounds. His past relationship and family struggles have shaped his approach to life. Will’s confidence and self-assuredness, which once repelled her, now become attractive to Anna as it’s something she longs to have in herself. As Anna’s life becomes more hectic, Will becomes a solid presence, whether helping her deal with a dead cat or encouraging her to advocate for competitive pay at her job. After they become lovers, Anna says, “He is tactile and familiar and unselfconscious” (247). Will becomes Anna’s healthy partner as he pushes her to grow in ways that make her a better, more fulfilled version of herself. In turn, Anna doesn’t ask Will to give up his dream of working in Paris to be with her. They both take a leap of faith in entering a relationship, not because they fit into a perfect compatibility model but because they see and accept each other completely.

Dan is Anna’s ex-husband and father to her two children. At first, Dan is an antagonistic force in Anna’s life as she adjusts to life as a single mother, navigates the complications of co-parenting, and still wrestles with how and why her marriage ended. She describes their complicated dynamic: “[…] this is what an ex-husband is: one minute exasperating and petty, the next, reminding you why you loved him in the first place” (71). The tension between Anna and Dan increases as Dan completely reinvents himself post-divorce and begins dating a much younger woman named Sylvie, whom Anna perceives as representing everything she couldn’t be for Dan. Dan becomes immersed in his new life, and though he and Anna have split custody, she takes on more of the physical and financial responsibility of raising them. Dan’s ability to quickly move on from their marriage highlights Anna’s struggles with dating and self-worth. Though she doesn’t desire reconciliation with Dan, his apparent ease in finding a new partner makes her question her desirability and whether she can move on. Their dynamic illustrates the uneven emotional aftermath of divorce; one partner may seem to transition smoothly while the other struggles to find a new start.

Dan’s relationship with Sylvie, a woman who seemingly fits the mold of a “perfect” new partner, is a foil to Anna’s sometimes messy journey of self-discovery. Sylvie represents a conventional post-divorce romance, as she is poised, put-together, and eager to integrate into Dan’s life. Seeing Dan in a new relationship forces Anna to confront her lingering insecurities and the fear of being left behind. However, as she grows through her dating experiment and evolving relationship with Will, she realizes that Sylvie’s presence in Dan’s life does not diminish her worth or happiness. Rather than viewing their marriage as a failure on her part, she comes to see it as a natural divergence in their respective paths. Hearing about Sylvie’s pregnancy brings Anna an epiphany about her journey with motherhood. It pushes her to speak to Dan about the imbalance in their co-parenting duties, leading to better communication. Dan represents the past Anna has outgrown and overcome, specifically the life she once thought she wanted but ultimately needed to move beyond. Through her interactions with him, she recognizes that true happiness does not come from fixing her past mistakes but from having the courage to accept her and Dan’s separate journeys moving forward yet remain united in their desire to love their children well.