The Fiancé Dilemma Summary, Characters and Themes

The Fiancé Dilemma by Elena Armas is a heartwarming, small-town romance filled with humor, charm, and self-discovery. 

Set in the picturesque community of Green Oaks, North Carolina, it follows the quirky and spirited Josie Moore, infamous for her four failed engagements. When a mix-up forces her to introduce Matthew Flanagan, her half-sister’s best friend, as her fifth fiancé, the two find themselves entangled in a charade of fake love. As they navigate wedding plans orchestrated by Josie’s overbearing father, unexpected emotions surface, leading to a heartfelt journey of growth, forgiveness, and an authentic connection that defies the odds.

Summary

Josie Moore is no stranger to romantic missteps, having been engaged four times before without ever making it down the aisle. 

As the recently acknowledged daughter of Andrew Underwood, a wealthy and image-conscious businessman, her personal history becomes a PR challenge when Andrew announces plans for a splashy autobiography. Josie, who already feels the weight of small-town gossip in Green Oaks, North Carolina, finds herself under even greater scrutiny. 

When Andrew’s overzealous PR manager, Bobby “Shark,” spots a ring on her finger, he assumes Josie is newly engaged, prompting her to blurt out a spontaneous—and false—confirmation. Enter Matthew Flanagan, Josie’s half-sister Adeline’s best friend, who unexpectedly arrives in Green Oaks seeking refuge after losing his job. 

To Josie’s dismay, he becomes the unwitting “fiancé” in her fabricated story.

Though initially reluctant, Matthew agrees to play along, sensing Josie’s desperation to keep up appearances. 

The ruse quickly spirals out of control as Andrew and Bobby seize the opportunity to stage an elaborate wedding, all while promoting Andrew’s book. Josie is swept into a whirlwind of wedding preparations, from cake tastings to dress fittings, with her father prioritizing public optics over her feelings. 

Meanwhile, the close-knit Green Oaks community watches with a mix of amusement and skepticism, given Josie’s romantic track record.

As Josie and Matthew spend more time together, their dynamic shifts. Despite their agreement to keep things strictly platonic, they share moments of vulnerability, playful banter, and an undeniable emotional connection. 

Matthew, protective and kind, proves to be a grounding presence for Josie, who struggles with insecurities about her past. In turn, Josie’s quirky, impulsive nature helps Matthew shed his guarded exterior, even as he keeps his job loss a secret.

Tensions come to a head during a bridal fitting, where Josie, overwhelmed by the pressure and haunted by memories of failed engagements, has a panic attack. Matthew steps in, offering comfort and reaffirming his support. 

This moment of honesty deepens their bond, pushing them closer to admitting their true feelings. Shortly after, during a high-profile event orchestrated by Andrew, the couple decides to come clean. 

Matthew publicly calls off the wedding but declares their real, mutual love, defying expectations and rejecting the façade they’ve been forced into.

The fallout leads to personal growth for both characters. Josie stands up to her father, setting boundaries and demanding respect, while Matthew embraces vulnerability, revealing his struggles to his family. In the end, Josie and Matthew emerge as a genuine couple, choosing love on their own terms. 

Their journey highlights themes of self-acceptance, forgiveness, and the courage to live authentically, leaving readers with a satisfying conclusion that celebrates emotional honesty and enduring connection.

Characters

Josie Moore

Josie Moore is the central protagonist of The Fiancé Dilemma, a quirky and impulsive woman who has had a turbulent romantic history. Having been engaged four times, Josie’s past is often a source of both humor and embarrassment in the small town of Green Oaks, where everyone knows everyone else’s business.

She is also the daughter of Andrew Underwood, a wealthy and high-profile figure, with whom she has only recently started to form a connection after years of estrangement. Josie has grown up with a sense of trying to impress others and hiding her insecurities, which is reflected in her tendency to blurt out exaggerated or absurd lies when stressed.

Despite this, Josie remains cheerful and caring, often playing the role of the town’s unofficial mayor, trying to balance her own desires with the pressure of meeting others’ expectations. Her journey throughout the story is about self-forgiveness and finding real love, as she learns to stand up for herself and stop letting others define her life.

Matthew Flanagan

Matthew Flanagan, the male lead, starts the story in a vulnerable and troubled state. He has recently lost his job and is hiding this fact from his family, which sets him on a temporary journey to Green Oaks to stay at a cabin belonging to his close friend Adeline.

Matthew is described as a nice, slightly shy man with a protective streak, particularly toward Josie. When he meets her, he is unexpectedly roped into the charade of being her fiancé to help her with the public relations dilemma posed by her father.

Though initially reluctant, Matthew goes along with it, and over time, he develops genuine feelings for Josie. His character arc revolves around embracing honesty and being true to himself, including revealing his unemployment to his family and supporting Josie in standing up for herself.

His growing affection for Josie is marked by a slow-burn romance that develops as he becomes her emotional rock.

Andrew Underwood

Andrew Underwood is Josie’s father, a wealthy and influential man who has long distanced himself from her. His primary concern is the public image of the Underwood family, and he hires a PR manager, Bobby, to manage his brand, especially as he prepares to release a book.

Throughout the story, Andrew’s priorities are shown to be focused on optics rather than on truly building a relationship with his daughter. His push for Josie to appear stable by being engaged again is not out of love or care but is motivated by his desire for a polished family image.

He is depicted as distant and often selfish, more concerned with how his actions appear to the public than with the emotional well-being of his daughter. However, toward the end of the novel, he begins to recognize the strain he has caused and starts to pull back, realizing that Josie deserves autonomy and respect.

Bobby “Shark”

Bobby, nicknamed “Shark,” is Andrew Underwood’s high-powered PR manager. He is intense, blunt, and unyielding in his approach to managing the Underwood family’s public image.

As soon as he arrives in Green Oaks and sees Josie’s engagement ring, he assumes that Josie is newly engaged and immediately begins to push the narrative for damage control. Bobby is the catalyst for much of the wedding frenzy that ensues, orchestrating every detail of the supposed wedding, from cake tastings to bridal fittings, all to keep the Underwood family’s public image intact.

Despite his heavy-handed tactics, Bobby’s presence is essential to the plot as he both enables and exacerbates the tension Josie feels about her public life and her father’s manipulation.

Adeline

Adeline is Josie’s half-sister or stepsister, who also appears in the previous book The Long Game. While not a central character in The Fiancé Dilemma, Adeline plays a supportive role in the story, as Matthew is her close friend.

Her relationship with Josie is important because it offers a contrast between the two women. Adeline’s presence highlights Josie’s deep-seated feelings of inadequacy and her desire for approval from her father.

The support that Adeline offers Matthew throughout his time in Green Oaks is a reflection of their close friendship, and her connection to the main characters helps create a fuller sense of the relationships within the story.

Themes

Forgiveness and The Journey Towards Self-Acceptance

One of the central themes of The Fiancé Dilemma is Josie’s journey of self-forgiveness and healing from the emotional baggage of her past. Over the course of the story, Josie grapples with the impact of her four failed engagements and the associated feelings of shame and inadequacy.

These past mistakes become public knowledge in Green Oaks, amplifying the pressure Josie feels to meet the expectations of others, particularly those of her high-profile father, Andrew. However, as the story progresses, Josie learns to recognize that her worth is not defined by her past romantic failures.

By confronting her insecurities, acknowledging her past, and ultimately choosing to forgive herself, Josie starts to embrace the possibility of true love without the need to conform to external pressures. This healing process isn’t easy and takes time, but it serves as a powerful reminder that growth often arises from confronting and accepting one’s flaws, rather than allowing them to dictate future actions.

Reclaiming Autonomy in the Face of Societal and Familial Expectations

A significant theme in The Fiancé Dilemma revolves around reclaiming one’s autonomy, especially when faced with the intense pressures of societal and familial expectations. Josie’s journey is characterized by the constant push and pull between her desires and the overwhelming influence of her father’s public image and the expectations of Green Oaks.

Her engagement, initially born out of a misunderstanding and fabricated for the sake of public relations, serves as a microcosm of the larger theme of autonomy. Josie’s father, Andrew, repeatedly tries to manipulate her personal life for the benefit of his public persona.

He seeks to use her “fifth engagement” as a means of portraying stability in his upcoming autobiography. Throughout the novel, Josie must assert her right to live her life on her own terms, which includes rejecting her father’s attempts to control her narrative.

This theme highlights the importance of setting boundaries, making personal decisions that align with one’s own values, and prioritizing authenticity over pleasing others.

Navigating the Complexities of Public Image versus Private Truth

Another intricate theme in the novel is the tension between maintaining a public image and confronting one’s private truths. Josie’s life becomes entangled in a public relations nightmare when her engagement to Matthew is misinterpreted as yet another public spectacle, meant to placate both her father’s ambitions and the prying eyes of the small-town community.

The media, as well as the residents of Green Oaks, all want to believe that Josie’s engagement is the “real thing” despite the fact that it was born out of a misunderstanding. Matthew, too, finds himself struggling with the pressure to live up to a “perfect” image—one that hides his recent job loss and the vulnerabilities he feels.

Throughout the novel, both Josie and Matthew learn the importance of reconciling their public personas with their authentic selves. As the plot unfolds, they come to realize that the most meaningful relationships are built on honesty, not carefully crafted facades.

This theme underscores the challenges individuals face when trying to balance their internal truths with the external expectations placed upon them by society and family.

The Transformative Power of Genuine Emotional Connections

The slow-burn romance between Josie and Matthew becomes the heart of the narrative, highlighting the transformative power of genuine emotional connections. What begins as a fabricated engagement for the sake of public image gradually evolves into a deep, real relationship based on mutual respect, affection, and shared vulnerabilities.

This theme is explored through the gradual progression of their bond, where physical attraction and emotional intimacy grow simultaneously. In the early stages, their connection is framed by humor, banter, and a growing understanding of each other’s personal struggles.

As they navigate the complexities of wedding planning and public expectations, they begin to recognize the depth of their feelings, moving beyond the initial charade of being a “fake fiancé” to a truly committed couple. This slow-burn romance, where both characters face challenges and emotional growth, emphasizes that love is not about grand gestures but about the quiet moments of understanding, care, and support.

The theme of emotional growth through a genuine relationship underscores the importance of patience, vulnerability, and self-awareness in fostering lasting connections.

Challenging the Notion of “Perfect” Love and Embracing Imperfections

A final critical theme in The Fiancé Dilemma is the challenge to the idealized notion of “perfect” love and the embrace of imperfections in relationships. Josie’s repeated failed engagements reflect her struggles with meeting societal expectations about love, marriage, and success.

Each previous engagement ended in disappointment, leading her to question her worthiness of true love. In contrast, Matthew’s presence in her life challenges the superficial concept of perfection.

Their relationship is not flawless, and they both have their own personal issues and baggage—Josie’s insecurities about her past and Matthew’s secret about his unemployment. Yet, it is through accepting and embracing these imperfections that they find a deeper connection.

Their journey teaches them that love does not require perfection but rather acceptance, compromise, and growth. This theme highlights that love is most meaningful when it is grounded in the reality of who we are, flaws and all, and it encourages readers to let go of unrealistic expectations in favor of building genuine, enduring relationships.