How to Get a Life in Ten Dates Summary, Characters and Themes

How to Get a Life in Ten Dates by Jenny L.  Howe is a smart and emotionally grounded contemporary romance that follows 25-year-old Haleigh Berkshire, a freelance editor whose life is defined by professional uncertainty, familial pressure, and unresolved love.

Caught between the expectations of her loved ones and her own quest for fulfillment, Haleigh launches a bold social experiment—ten dates set up by the people closest to her—to prove just how absurd and exhausting modern dating can be.  Along the way, she navigates complicated relationships, particularly with her long-time best friend Jack, and begins to uncover what she truly wants in love, work, and herself.

Summary

Haleigh Berkshire is done with modern dating—or at least, that’s how she feels after enduring a slew of mismatched encounters that include an off-putting match with someone called BeefCake20 and an ice-cold real-life date with a woman named Annie.  Her love life is nothing short of dismal, and her emotional compass keeps circling back to Jack, her best friend of over a decade.

Jack is everything she wants—kind, loyal, funny—but he’s also someone she’s determined to keep in the friend zone after a near-romantic disaster in their past.

Home isn’t much of a haven either.  Her roommate Stanton is supportive but insistent that she take more risks in love, while her mother and grandfather pepper her with questions about her relationship status and her unconventional freelance job.

Haleigh’s simmering frustration reaches a boiling point during a trip to the grocery store with her family, culminating in a feeling of emotional overload.  In a moment of clarity, Jack proposes a challenge: allow five people in her life to each set her up on two dates.

If none of the ten dates result in a connection, her family must drop the topic of her love life for six months.  Haleigh, exasperated and eager to reclaim agency over her life, agrees.

She gathers her “date-pocalypse” committee—Joey (her successful sister), her mother, Pépère (her grandfather), Stanton, and Jack—and pitches the plan.  With clearly defined boundaries like honesty about her body type and a post-experiment moratorium on criticism, the group agrees.

The dates that follow are chaotic, mismatched, and revealing.  From a brunch interrupted by an emotional support cockatoo to a hiking date that leaves Haleigh miserable and muddy, the experiment is less about finding a partner and more about asserting her autonomy.

The journey becomes even more complex when Haleigh meets Brian, a charming veterinarian picked by Stanton.  Their connection is immediate.

Brian is thoughtful and easy to be with, making her feel accepted in a way she’s rarely experienced.  They share messy but intimate dates, vulnerable conversations, and mutual admiration.

He supports her aspirations and even helps her prepare for a job interview at High Tower Publishing—her dream career opportunity.

At the same time, Jack’s emotional undercurrents start rising.  He becomes a more present and protective figure in Haleigh’s life, from rescuing her from disastrous dates to showing signs of subtle jealousy.

His carefully hidden affection begins slipping through the cracks.  A drunken “I love you” at a party sends Haleigh into a spiral, unsure of whether Jack truly meant it or if it was just alcohol-induced nostalgia.

The push-and-pull between them intensifies, as Jack remains a steady source of emotional support, grounding her through moments of self-doubt, especially after a botched interview at High Tower leaves her reeling.

Despite her best efforts, Haleigh finds herself emotionally caught between two men: Brian, whose charm, stability, and genuine kindness present a safe, loving future; and Jack, whose familiarity, shared history, and deep-rooted affection stir something deeper.  A series of candid moments with her sisters and her mother help Haleigh confront her fears, particularly about her complicated past with Jack and the real reason she’s been afraid to risk their friendship.

As her second interview with High Tower approaches, so does clarity.  Haleigh recognizes that her connection with Brian, while meaningful, lacks the emotional gravity she feels with Jack.

When Brian admits he isn’t much of a reader—something Haleigh holds dear—it crystallizes her realization that they aren’t fundamentally aligned.  After one final romantic evening, she gently breaks up with Brian.

He accepts her decision with grace, even offering her a job at his animal rescue sanctuary, a role that matches her desire for meaningful work and autonomy.

With the romantic field cleared, Haleigh and Jack share an evening that solidifies everything they’ve always danced around.  They reconnect, both emotionally and physically, finally addressing the unspoken feelings that have shaped their friendship for years.

This time, there are no hesitations—only acceptance.  Their relationship deepens into a romantic partnership grounded in history, emotional reciprocity, and shared understanding.

Haleigh’s growth doesn’t stop at love.  She learns to articulate her desires, assert her professional ambitions, and accept her own pace in a world that constantly demands more.

When Jack experiences a mental health crisis from work-related stress, Haleigh becomes his anchor, guiding him with the same compassion he once offered her.  The roles reverse, proving that love, for them, means mutual support and balanced vulnerability.

The story culminates at a family gathering, where Haleigh receives something she’s long craved—recognition and respect from the people who once doubted her.  In a moment of sweet, understated joy, Jack proposes using a toy narwhal that holds personal significance for them both.

Haleigh says yes, not just to Jack, but to a version of life where she is loved as she is, unconditionally.

How to Get a Life in Ten Dates is more than a romantic comedy; it’s a story of self-definition.  Through awkward encounters, romantic revelations, and deep emotional reckoning, Haleigh reclaims her voice, her heart, and her future.

Her journey affirms that love isn’t about finding someone to complete you, but rather discovering the courage to live a life that reflects who you already are.

Characters

Haleigh Berkshire

Haleigh Berkshire is the vibrant emotional center of How to Get a Life in Ten Dates.  At twenty-five, she is a self-employed freelance editor navigating the chaotic and frequently demoralizing landscape of modern dating, particularly as a fat woman in a world that remains deeply judgmental.

Her voice is funny, self-aware, and filled with vulnerability, reflecting a lifetime of internalized anxiety and societal pressure.  From the first failed swipe to her impassioned pitch for the “date-pocalypse,” Haleigh emerges as a woman striving to reclaim agency over her own narrative.

Despite familial pressure to conform—her mother and grandfather push for a more “traditional” lifestyle—Haleigh resists with tenacity and wit, even as she deeply craves validation.  Her evolving romantic journey, especially her conflicted feelings for Jack and growing affection for Brian, reveals a layered internal struggle between safety and self-discovery, comfort and growth.

Haleigh’s ultimate arc is not just about finding love, but about asserting the legitimacy of her desires, career, and body.  Her resilience shines through each awkward date, each moment of vulnerability, and ultimately through her brave, wholehearted decision to follow her truth—both in love and in life.

Jack

Jack serves as both Haleigh’s emotional anchor and her most persistent source of inner turmoil.  Their decade-long friendship is steeped in comfort, familiarity, and a romantic history that still quietly shadows every shared laugh and knowing glance.

Jack is tender, reliable, and unfailingly supportive, the kind of person who stages fake emergencies to rescue Haleigh from bad dates and shows up with horror movies and donuts when she’s low.  Yet beneath his steady presence lies a guarded longing and jealousy, particularly as Haleigh begins seeing Brian.

His struggle to suppress his feelings manifests in stress behaviors—obsessive cleaning, emotional fatigue, and an almost subconscious attempt to sabotage Haleigh’s budding romance with Brian.  Jack’s emotional arc parallels Haleigh’s in complexity: he must confront his own hesitations and fears about their past, and eventually acknowledge the depth of his love.

His transformation culminates not in grand declarations, but in small, meaningful gestures that affirm his commitment—culminating in his heartfelt proposal with a toy narwhal, a symbol of their unique bond.  Jack’s journey from best friend to life partner is quietly profound, grounded in shared history and earned vulnerability.

Brian

Brian enters Haleigh’s life as a breath of fresh, grounded air.  A kind-hearted veterinarian, he offers something Haleigh rarely experiences in dating: gentle curiosity, respect, and emotional safety.

Their early interactions—spilling dumplings, nervous laughter—establish a connection based on acceptance rather than judgment.  Brian listens without trying to fix, supports without expecting reward, and provides a low-pressure space in which Haleigh can just be.

His kindness extends beyond romance; even when Haleigh ends things, he responds with understanding, offering her a job at Sundae’s Sanctuary.  Brian represents the life Haleigh might have had—secure, peaceful, and filled with small joys.

But their relationship also exposes differences that matter.  His disinterest in reading, though seemingly minor, is emblematic of a broader emotional disconnect.

Despite their affection, the spark between them lacks the history and soul-deep recognition that Jack provides.  Brian’s presence in the story is vital not because he is “the one,” but because he helps Haleigh recognize what she truly needs in a partner.

He is a catalyst for self-discovery, the kind of partner who, even in heartbreak, leaves someone better than he found them.

Stanton

Stanton is Haleigh’s flamboyant, supportive roommate and a refreshing burst of levity and wisdom.  As a television producer with a flair for the dramatic, Stanton encourages Haleigh to embrace life more boldly.

He’s a loyal friend who doesn’t hesitate to call out her self-doubt while cheering her on from the sidelines.  Stanton is instrumental in nudging her toward the dating experiment and serves as a stabilizing emotional presence throughout.

He embodies queer joy, fierce friendship, and a deep well of empathy, offering Haleigh the kind of non-romantic love that grounds her when everything else feels uncertain.  His home is a sanctuary, his presence a source of laughter and occasional tough love.

Stanton’s role, while not as emotionally central as Jack or Brian, is essential to Haleigh’s personal growth.  He represents chosen family and the kind of companionship that doesn’t demand transformation but celebrates authenticity.

Joey

Joey, Haleigh’s high-achieving sister, initially appears to be a foil to Haleigh—poised, successful, and seemingly aligned with their family’s traditional expectations.  However, as the story progresses, Joey reveals her own vulnerabilities and hidden insecurities.

She, too, is burdened by the weight of familial pressure and the demand to perform perfection.  The dynamic between the sisters shifts from subtle rivalry to authentic understanding, especially when Haleigh reaches out for help preparing for her publishing interview.

Joey’s character deepens through this mutual recognition of shared struggles.  She’s not merely the golden child; she’s a woman doing her best to manage expectations, just like Haleigh.

Their relationship evolves into one of mutual respect, where both sisters acknowledge the different ways they’re trying to carve out meaningful lives.

Pépère

Pépère, Haleigh’s grandfather, is a symbol of generational tradition, love, and occasional stubbornness.  He cares deeply for Haleigh, but his affection often manifests as concern for her future stability.

His choice of Bradley Cooper (not the actor) as a date for Haleigh underscores his belief in conventional success and financial security.  Yet even when his ideas clash with Haleigh’s values, his love is evident.

Pépère represents the older worldview Haleigh is trying to navigate and gently challenge.  While his intentions are well-meaning, they also reflect the societal narratives Haleigh seeks to push back against.

Through him, the novel captures the tension between familial love and generational misunderstanding, as well as the possibility of compassion even amid disagreement.

Haleigh’s Mother

Haleigh’s mother epitomizes the dual nature of familial support and pressure.  She wants what’s best for her daughter, but often filters that desire through a narrow definition of success—stable employment, a conventional partner, and visible markers of adult life.

Her selection of Pete (and Scooter the cockatoo) as a date is both comical and revealing, suggesting her good intentions are frequently undermined by a lack of understanding.  Still, there’s a genuine love in her interactions with Haleigh, particularly in the way she participates in the dating challenge and tries, in her own way, to support her daughter.

Over time, the mother-daughter relationship reflects a slow, imperfect process of mutual recognition.  Though her mother may not always “get” Haleigh’s world, she remains a consistent, if sometimes misguided, presence in it.

Their evolving bond highlights the ongoing negotiation between individuality and familial closeness.

Themes

Body Image and Societal Expectations

Haleigh’s journey through dating and self-definition is heavily shaped by how society views and treats fat bodies, and the emotional toll that comes from inhabiting such a space.  Her decision to embark on the “date-pocalypse” isn’t merely a whimsical romantic experiment—it is a response to repeated experiences of exclusion, dismissal, and discomfort in a dating world that privileges thinness and traditional beauty standards.

She attempts to reclaim her narrative by enforcing upfront transparency about her body in the pre-date questionnaires, a move that speaks volumes about the defensive vigilance fat women are often forced to maintain just to avoid humiliation.  Her date with Bradley Cooper is a particularly stark reminder of the kind of condescension and microaggressions she has to endure—his controlling behavior, presumption of authority over her financial decisions, and efforts to fix her freelance life underscore the intersection of body-based and economic biases.

These experiences collectively paint a sobering picture of how women who exist outside normative standards are routinely pressured to apologize for, justify, or “improve” their existence.  But How to Get a Life in Ten Dates doesn’t simply dwell in the discomfort; it charts Haleigh’s growth from defensiveness to power.

Over time, she begins to recognize that her body isn’t the problem—society’s gaze is.  Her interactions with Brian are healing not because he “accepts” her but because he doesn’t see her body as something that needs excusing.

The novel ultimately illustrates the profound relief and transformation that occur when a person begins to separate their self-worth from societal expectations about appearance.

Friendship and Emotional Boundaries

The relationship between Haleigh and Jack forms the emotional core of the novel, but it is also a study in the complexity of platonic intimacy and the fragility of emotional boundaries.  Their bond is deep, sincere, and rooted in years of shared memories and silent support.

Yet, this very closeness breeds confusion.  For Haleigh, Jack is the emotional home she returns to after every failed date, after every pang of doubt or fear, and after every professional and personal setback.

Their inside jokes, shared routines, and unspoken language create a relationship that feels more like a partnership than many romantic connections.  The complication arises from the fact that their love has never been fully defined or acknowledged, instead living in the liminal space between “just friends” and something more.

Jack’s protective behavior and emotional availability blur the lines, and Haleigh’s dependence on him reflects both the comfort of familiarity and the danger of avoiding emotional risk.  As Jack begins to show signs of possessiveness and emotional strain, Haleigh is forced to confront the cost of their ambiguity.

She realizes that emotional boundaries are not just about keeping others out but about protecting one’s own clarity and growth.  When Jack finally confesses his feelings and they allow themselves to acknowledge the depth of their love, it is not just a romantic turning point—it is the culmination of years of emotional entanglement finally finding form.

Their relationship transforms only after they allow it to be redefined with honesty, vulnerability, and consent.

Autonomy and Reclaiming Life Narratives

Haleigh’s decision to let others set her up on ten dates might initially appear like a relinquishment of control, but it evolves into a powerful act of reclaiming her autonomy.  The novel positions the “date-pocalypse” not as a search for love but as a confrontation of all the narratives imposed upon her—by family, society, even herself.

At every turn, Haleigh is burdened with expectations: her mother and grandfather want her to pursue a stable, conventional life; her sister Joey sees her as adrift; and her own inner critic is often the harshest of all.  Her freelancing career, though fulfilling, is a symbol of that non-traditional path that others see as temporary or inferior.

Agreeing to the dating challenge on her terms—with explicit boundaries and rules—becomes an act of resistance.  She is not trying to be chosen; she is choosing how and if she wants to participate in the romantic marketplace.

Her decision to walk away from a relationship with Brian, despite his kindness, demonstrates how she no longer feels compelled to settle for something just because it is safe or available.  Similarly, her vulnerable pursuit of a dream job in publishing, and her willingness to bounce back from a failed interview, show a shift from fear-based decisions to bold self-definition.

By the time Haleigh accepts Jack’s proposal, it is not a surrender to destiny but a conscious affirmation of love and partnership on her own terms.  She has authored her own story.

Mental Health and Emotional Resilience

Throughout the novel, Haleigh’s mental health is both a source of struggle and a wellspring of strength.  Her anxiety isn’t romanticized or exaggerated; it is presented as a real, shaping force in her life—manifesting during dates, job interviews, and emotionally charged conversations.

Her panic during moments like the date with Bradley or the publishing interview reveals how deeply rooted her fears of failure, rejection, and inadequacy are.  Yet what sets How to Get a Life in Ten Dates apart is its insistence that anxiety doesn’t preclude resilience.

Haleigh doesn’t conquer her anxiety in some final, triumphant moment; instead, she learns how to live with it, how to understand it, and most importantly, how to create spaces and relationships that accommodate and respect it.  Her support system—particularly Stanton, Brian, and Jack—play a crucial role, but her greatest growth comes when she learns to support herself.

Her proactive decision to help Jack through his own mental health spiral further demonstrates her emotional evolution.  She becomes the grounding force in his life just as he had once been for her.

This reciprocity not only strengthens their bond but also validates the narrative that emotionally vulnerable people can still be caregivers and leaders in relationships.  The novel champions a vision of love and self-worth grounded in compassion, mutual aid, and the courage to keep showing up even when the world feels overwhelming.

Love as Safe Harbor and Mutual Growth

The romance between Haleigh and Jack ultimately transcends the cliché of “friends to lovers” because it is built not just on chemistry or longing but on years of growth, trust, and mutual healing.  Their love is not a dramatic revelation but a quiet unfolding that feels inevitable in retrospect.

What makes their connection unique is how fully they see each other—not as idealized figures but as flawed, anxious, complicated people trying to do their best.  Jack is not a perfect romantic lead; he makes mistakes, suppresses his emotions, and struggles with burnout.

Haleigh is not a passive recipient of affection; she is actively navigating her own maze of fears, ambitions, and emotional baggage.  Their journey to partnership is not about one saving the other but about choosing each other repeatedly—through awkward confessions, missed signals, and moments of deep care.

The symbolism of the narwhal proposal encapsulates their dynamic perfectly: quirky, personal, and steeped in shared history.  Their love does not “fix” them, but it offers a safe place to grow.

In the end, the romance is powerful not because it defies odds but because it honors the quiet, steadfast work of building a life together.  Love, in this story, is not an escape but a foundation—a place where each person is fully seen, held, and celebrated for who they are and who they are becoming.