Is She Really Going Out with Him Summary, Characters and Themes

Is She Really Going Out with Him? by Sophie Cousens is a heartwarming and hilarious contemporary romance about love, second chances, and self-discovery. 

The story follows Anna Appleby, a recently divorced single mother who, after swearing off romance, is forced to jump back into the dating pool for the sake of her job. But there’s a catch—her children get to pick her dates, and online apps are strictly off-limits. As Anna navigates a series of disastrous yet comedic encounters, she finds herself drawn to an unexpected connection with her charming and competitive colleague, Will Havers. With humor, wit, and emotional depth, the novel explores how love isn’t about fairy-tale perfection but about finding someone who truly sees and values you.

Summary

Anna Appleby has officially sworn off dating. After a painful divorce from her ex-husband Dan, she’s content with her life as a single mother to Ethan and Jess, focusing on her career as a columnist for Bath Living. 

Who needs love when she has a cat, control of the remote, and freedom from the chaos of modern dating? 

However, when her position at the magazine is threatened by her office rival, Will Havers, she pitches a daring idea to save her job: she’ll go on seven dates—chosen by her children—all without using dating apps.

At first, Anna treats the experiment as nothing more than work, fully expecting the dates to be a disaster. 

And, as expected, they are. From an egoistic celebrity to a reckless driver with road rage, each encounter proves more disastrous than the last. Her kids, though well-intentioned, set her up for failure, suggesting speed dating events, awkward coffee shop meetups, and even a hopeful run-in with their friendly mailman. 

Every outing reminds Anna why she had sworn off dating in the first place. Meanwhile, her ex-husband Dan isn’t making life any easier. Now in a relationship with someone new, he’s about to have another child, stirring up old wounds and insecurities in Anna.

Throughout this chaotic dating experiment, Anna’s dynamic with Will begins to shift. What started as a workplace rivalry—filled with sarcastic jabs and competition—gradually develops into something deeper. Will, always confident and a bit cocky, seems to genuinely enjoy sparring with Anna, but beneath his teasing, there’s an undeniable chemistry brewing between them. 

As they spend more time together—whether it’s working late, exchanging sharp banter, or sharing quiet moments of vulnerability—Anna starts questioning whether she’s been looking for love in the wrong places all along.

Despite their growing closeness, Anna refuses to acknowledge her feelings. She convinces herself that real love should follow a set pattern, that she must go through the motions of dating “the right way” before she can find happiness again. 

However, as her dates continue to fail spectacularly, she begins to recognize a crucial truth: love isn’t about checking boxes or following a script—it’s about genuine connection.

Things come to a head when Anna and Will share an unexpected yet deeply intimate moment. Just as she’s on the verge of opening up, a misunderstanding drives them apart, leaving Anna confused and emotionally vulnerable. She begins to spiral, questioning not just her romantic future but also her worth outside of societal expectations. A particularly embarrassing moment during a school reading session—where she rants about fairy tales misleading people about love—becomes a turning point. She realizes she’s spent too much time trying to fit into a predetermined narrative rather than embracing what truly makes her happy.

Determined to take control of her own story, Anna finally acknowledges her feelings for Will. 

She seeks him out, willing to take a chance despite her fears of repeating past mistakes. In a heartfelt confession, she lets go of her doubts and embraces the messy, imperfect, but deeply real love she’s found with him.

The novel concludes with Anna no longer bound by the need for a picture-perfect romance. Instead, she chooses a relationship that feels right for her—one based on mutual understanding, laughter, and shared imperfections. 

As she moves forward with Will, she embraces the idea that love isn’t about fairy-tale endings but about finding someone who sees and values you for who you truly are.

Characters

Anna Appleby

Anna, the central character, is a recently divorced, middle-aged mother of two, juggling the complexities of single motherhood, career pressures, and the societal expectations of finding love again. Throughout the story, Anna evolves from a woman who has shut herself off from romantic relationships to one who learns to embrace vulnerability.

Initially, she seeks love through external expectations—dating different men in traditional settings suggested by her children. Over time, she comes to realize that the best connections are those that emerge unexpectedly and naturally.

Her transformation is not just about finding romantic love, but also about self-acceptance. She learns that love does not fit into a neat, fairy-tale package.

Will Havers

Will starts as Anna’s workplace rival, but his relationship with her deepens throughout the novel. He is charming, witty, and intelligent, but beneath his cocky exterior, there is a more vulnerable side that he reveals as he becomes closer to Anna.

Will’s gradual shift from an office competitor to a romantic partner highlights the theme of love emerging in unexpected ways. His relationship with Anna isn’t without complications—misunderstandings and moments of emotional distance arise—but Will is pivotal in helping Anna break away from her fixed ideas of romance and embrace a relationship based on genuine connection.

Dan Appleby

Anna’s ex-husband, Dan, plays a significant role in the story, despite not being a primary character. He represents the traditional expectations of family and love that Anna is trying to move away from.

Dan’s new relationship, coupled with the arrival of a child with his new partner, further complicates Anna’s emotional journey. His continued presence serves as a reminder of the life Anna once had and a push for her to redefine her idea of happiness and romantic fulfillment.

Ethan and Jess

Anna’s children, Ethan and Jess, are central to the plot as they unintentionally push Anna back into the dating world. Their innocence, suggestions for dates, and candidness help to reveal Anna’s inner conflicts and desires.

Through their eyes, the reader sees Anna not just as a mother, but as a woman with her own dreams, fears, and evolving identity. They provide both comic relief and poignant moments of realization for Anna, guiding her towards a greater understanding of herself and her needs in relationships.

Themes

The Struggle Between Societal Expectations and Personal Desires in the Search for Love

Throughout the novel, Anna grapples with the tension between society’s traditional narratives of love and her own personal desires. After her divorce, Anna feels the weight of expectations placed on single mothers, especially in terms of their need to find love again.

These expectations, often steeped in conventional romantic tropes such as online dating and matchmaking, conflict with Anna’s desire for something more organic and less formulaic. This internal struggle is heightened by the pressures from her work, where her column about dating becomes a reflection of these societal norms.

The novel explores the concept of dating as a performance, showing that the search for love often feels like an imposed task rather than an organic experience. Eventually, Anna’s journey teaches her that love cannot be dictated by external factors, and that true connection is found when one allows themselves the freedom to redefine their desires.

The Power of Vulnerability in Building Meaningful Relationships

One of the key themes of the book is the idea that vulnerability is crucial for genuine emotional connection. Anna starts the novel resistant to opening up, particularly when it comes to romantic relationships.

She holds onto her belief that maintaining control of her life—both in her career and her personal affairs—is the key to avoiding further heartbreak. However, as her interactions with Will evolve, she begins to realize that vulnerability is not a weakness, but a strength.

Her willingness to open up and be emotionally available leads to deeper, more meaningful connections, not just with Will, but also with her children and even with herself. Will’s character is similarly shaped by his own vulnerabilities, and together they learn that true intimacy is born from sharing fears, dreams, and flaws without the need for perfection or pretense.

Rewriting the Narrative of Love

The novel explores how traditional fairy tales and idealized notions of romance can be limiting and unrealistic. Anna’s experience with love, especially post-divorce, is messy, awkward, and anything but perfect, but it is through these imperfect moments that she finds real connection.

The fairy-tale endings Anna once believed in are deconstructed, as she learns that love doesn’t follow a predictable storyline. From her disastrous dates to her evolving relationship with Will, Anna realizes that love is not about checking off boxes from a societal script, but about authentic connection.

This theme invites readers to rethink the romantic ideals often portrayed in media and literature. It challenges the notion that love must fit a conventional mold to be valid.

Learning to Choose One’s Own Path

Anna’s journey is ultimately about self-discovery and personal growth. Throughout the novel, she evolves from a woman who feels defined by her role as a mother and ex-wife to someone who begins to reclaim her identity as an individual.

As she faces the ups and downs of dating, work pressures, and motherhood, she begins to realize that she is worthy of love—not because she fits into a traditional mold, but because she is a unique and multifaceted person.

Anna’s relationship with Will symbolizes this growth, as she learns to embrace her flaws, her mistakes, and her desires. The theme of self-acceptance emphasizes the importance of recognizing one’s own value and choosing a path that aligns with personal happiness rather than conforming to external expectations.

Through this theme, the novel highlights the transformative power of letting go of societal pressures and learning to trust one’s own instincts when it comes to matters of love and self-worth.