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 delightful rom-com that explores the ups and downs of modern dating and the complexities of love and friendship.
The story follows Haleigh Berkshire, a plus-size freelance editor who’s had enough of disappointing dates and societal pressures to find the “perfect” partner. To prove that finding true love isn’t as easy as it seems, she sets a challenge: her family and friends will pick ten dates for her. However, amidst the chaos, she begins to realize that the perfect match might have been by her side all along—her best friend, Jack.
Summary
Haleigh Berkshire, a plus-size freelance editor, has had enough of the modern dating world. After yet another terrible date, she feels disillusioned with the whole process. The disappointing encounters make her question if real love even exists. Haleigh confides in her best friend, Jack Brooks, about her frustrations.
They share a close, easy-going friendship, having known each other for years, and Jack often comforts her during her romantic struggles. After one such disastrous date, Haleigh comes up with a plan to show her family that dating is not as simple as it seems.
Her challenge is simple: her family and friends will pick 10 dates for her, and if none of them work out, she gets a 6-month break from dating.
The rules are set, and Haleigh’s mom, grandfather Pépère, sister Joey, best friend Jack, and roommate Stanton will each choose two candidates for her. To her surprise, Jack insists on picking two of her dates as well. Haleigh is reluctant at first, but she agrees, and the game begins.
The first set of dates proves to be a disaster.
The first date, chosen by Haleigh’s mom, is with a man who barely speaks, making for an awkward evening. The second date, picked by her Pépère, is with a man who is old-fashioned and brings up marriage and family too soon.
Next, Stanton arranges a date with a self-absorbed influencer who talks only about herself. After these disappointing encounters, Haleigh vents to Jack, who comforts her, but she begins to wonder if she’s even up for continuing the challenge.
Haleigh’s sister Joey reminds her that she needs to be in a relationship, as being single is seen as something undesirable in their family. Joey’s insistence, along with the pressure from the other dates, makes Haleigh feel even more lost.
But as the dates continue, something unexpected happens—Haleigh starts to notice Jack acting differently. She feels an undeniable warmth when he’s around, and the comfort she has always taken for granted begins to feel like something deeper.
The next set of dates only brings more confusion. Haleigh goes on a date with Joey’s choice, a lawyer who is attractive but too robotic to spark any chemistry. Jack’s pick is a funny teacher, a refreshing change, but again, there’s no romantic spark.
The other dates, including a doctor and a bookstore owner, also fail to leave a lasting impression. But in the middle of all this, Haleigh starts to see Jack in a new light, and the lines between friendship and love begin to blur.
In the final stretch of the challenge, Haleigh goes on a date with a personal trainer, the last person picked by Jack.
While Haleigh enjoys herself, she starts noticing a subtle jealousy in Jack’s behavior. This triggers a revelation—Haleigh realizes she doesn’t want to be with anyone except Jack. However, Jack begins to distance himself, and Haleigh fears he’s found someone else.
Heartbroken, Haleigh sabotages her final date on purpose, convinced that no one can compare to Jack. She finally admits to herself that she has always been in love with him.
When she confronts Jack about his behavior, he admits he had been trying to set her up with someone else, hoping she would move on from him. Jack confesses that he never stopped loving her either, and they have a flashback to a life-changing moment during a vacation in Hawaii years ago.
On that trip, they both confessed their feelings but were too afraid to act on them, fearing it would ruin their friendship.
In the end, Haleigh realizes that all the failed dates weren’t truly failures—they led her to understand what she had been looking for all along. Jack becomes her “final date,” and they both embrace their love for each other, no longer afraid of the risks love entails.
The story concludes with Haleigh and Jack finally transitioning from best friends to lovers, marking a joyful and fulfilling end to their long and complicated journey.
“How to Get a Life in Ten Dates” is a heartwarming tale about friendship, love, and the challenges of modern dating. Haleigh’s journey is filled with humor, emotional growth, and the realization that sometimes, the person you’re meant to be with is already by your side.
Characters
Haleigh Berkshire
Haleigh Berkshire, the protagonist, is a plus-size freelance editor who is tired of the modern dating world. She is independent, sarcastic, and struggles with body image issues, which are often exacerbated by her experiences on dates and societal expectations.
Haleigh’s journey is one of self-discovery, where she learns to love herself and embrace who she truly is. Despite her external confidence, Haleigh is vulnerable and deeply sensitive to the idea of finding someone who will accept her for all that she is.
Her relationship with Jack, her best friend, is central to her growth. Throughout the book, she shifts from seeing Jack as just a friend to realizing he is the one person she’s been looking for all along.
This transition is not just romantic but emotional as well, as she learns to trust her own choices and desires.
Jack Brooks
Jack Brooks, Haleigh’s best friend and eventual love interest, is a funny, easygoing, and caring character. He has known Haleigh for years and has always been a supportive friend, offering comfort and advice.
His actions throughout the story are complicated by his own feelings for Haleigh, which he tries to suppress for fear of ruining their friendship. Jack’s character arc revolves around his struggle to balance his love for Haleigh with his desire to protect their friendship.
He initially participates in Haleigh’s dating challenge by picking two dates for her, but as the story progresses, it becomes clear that he has always been in love with her. Jack’s jealousy when Haleigh starts dating others hints at his deep feelings.
The eventual revelation that he was pushing her to move on in order to preserve their friendship shows how conflicted he is. His love for Haleigh is ultimately selfless, and their transition from friends to lovers is both tender and long-awaited.
Joey
Joey, Haleigh’s younger sister, is portrayed as pragmatic and driven. She is very much in tune with societal pressures and believes that Haleigh should be actively seeking a partner.
Joey’s perspective on relationships often clashes with Haleigh’s more cynical views, especially regarding the necessity of having a romantic relationship. Throughout the story, Joey plays the role of the well-meaning but slightly overbearing sibling, encouraging Haleigh to push through the discomfort and keep dating.
While Joey’s intentions are good, she doesn’t fully understand her sister’s deeper needs or feelings. Her character, though supportive, doesn’t fully realize that Haleigh’s struggle is less about finding a partner and more about realizing what she truly wants.
Stanton
Stanton is Haleigh’s roommate and a fun-loving, fashion-forward character. He is the more lighthearted of Haleigh’s friends and brings comic relief to the story.
Stanton plays a significant role in setting up one of Haleigh’s disastrous dates with a self-obsessed influencer. His role in the story is to represent the “modern” perspective on dating, with a focus on appearance and surface-level connections.
While he does care for Haleigh, his understanding of relationships is more about novelty and aesthetics than deeper emotional connections. His playful and somewhat shallow personality contrasts with the more serious, introspective nature of Haleigh, making their dynamic interesting.
Pépère
Pépère, Haleigh’s grandfather, is a charming, old-fashioned man who brings a sense of tradition and wisdom to the story. His choices for Haleigh’s dates reflect his more traditional views on relationships, and his insistence on marriage early in conversations is both endearing and awkward.
Pépère’s character highlights the generational gap in views on dating and love. While his intentions are good, his understanding of modern relationships is somewhat outdated.
Nevertheless, Pépère’s character serves as a reminder of Haleigh’s roots and her family’s influence on her life and choices. His involvement in the dating challenge adds a touch of humor and warmth to the overall story.
Themes
The Struggles of Modern Dating and the Inescapable Search for Connection
In How to Get a Life in Ten Dates, the protagonist Haleigh Berkshire navigates a series of awkward, uncomfortable, and at times downright bizarre dates, which highlight the challenges of modern dating. This theme is portrayed with humor, but it’s also a poignant commentary on the unrealistic expectations that often come with finding love today.
Haleigh’s disastrous experiences on her dates serve as a reflection of how difficult it can be to find a meaningful connection in a world where superficiality, miscommunication, and incompatible expectations are rampant. Whether it’s the pressure to meet societal beauty standards or the constant comparisons in online dating, the novel presents a clear image of how exhausting the search for love can be, making it all the more satisfying when Haleigh realizes that the answer may have been right in front of her all along.
The Emotional Complexities of Friendships That Blur Into Romance
The relationship between Haleigh and her best friend Jack is one of the most compelling and intricate parts of the story. Their deep-rooted bond, filled with years of shared memories, makes the transition from friendship to romantic love both difficult and inevitable.
The theme of “friends to lovers” is explored with sensitivity and depth, showcasing how the line between platonic and romantic feelings can become increasingly blurred, especially when both individuals harbor unspoken emotions. The emotional complexities of their relationship create a tension throughout the book, as both Haleigh and Jack avoid acknowledging their growing feelings for fear of ruining their cherished friendship.
This theme touches on the delicate balance of preserving a friendship while simultaneously confronting feelings that may change the dynamic forever. Ultimately, the emotional journey that both characters undergo is a testament to the transformative power of love, particularly the kind that develops over time, grounded in understanding and shared history.
The Psychological Weight of Societal and Familial Expectations on Personal Choices
Another significant theme in the book is the societal and familial pressure to find a partner. From the outset, Haleigh faces constant reminders from her family about her single status, with well-meaning but intrusive suggestions and expectations.
Her sister Joey, for example, keeps pushing her to find a partner, believing that being single somehow reflects poorly on her. The book delves into how these pressures can shape a person’s self-worth and complicate their decision-making, especially when it comes to choosing a romantic partner.
Haleigh’s experiment of letting her family and friends set her up on dates illustrates just how difficult it can be to make authentic choices when external forces are at play. The theme speaks to the broader issue of how societal norms often dictate personal life decisions, making it harder to trust one’s instincts and desires.
Haleigh’s journey of self-discovery ultimately challenges these norms, suggesting that true happiness lies in making decisions based on personal fulfillment, rather than the expectations of others.
The Disillusionment of Self-Worth and the Empowerment of Learning to Trust One’s Own Choices
At its core, How to Get a Life in Ten Dates is about Haleigh’s growth as an individual, both in her personal and romantic life. A key theme of the book is the exploration of self-worth and how it can be easily influenced by outside opinions, especially in the dating world.
Throughout the story, Haleigh struggles with her self-image, particularly as a plus-sized woman in a society that often prioritizes physical appearance. Her early frustrations with dating reflect a deeper internal conflict about her own value.
However, as the story progresses, Haleigh begins to learn that her worth isn’t defined by the judgments of others, whether they come from online dating, her family’s expectations, or even her own insecurities. This theme is highlighted through her evolving relationship with Jack, as she begins to trust her feelings and make decisions that align with her own desires, not the external pressures around her.
The book ultimately champions the idea of embracing self-love and the importance of trusting one’s own choices, both in relationships and in life.
The Tension Between Rules and Feelings in Romantic Relationships
The tension between adhering to self-imposed rules and allowing genuine feelings to dictate romantic choices is another central theme in the book. At the start, Haleigh sets clear boundaries for herself, and even her interactions with Jack are governed by a set of unspoken rules aimed at preserving their friendship.
However, as their relationship develops, these rules begin to clash with their growing feelings for each other. The story explores how rigid rules, whether they come from personal convictions or societal norms, often stand in the way of authentic connection.
Haleigh’s challenge, where her family and friends choose her dates, also reflects the idea of following rules and systems in the quest for love, which ultimately fails to deliver the kind of connection she seeks. The theme emphasizes that love cannot be contained by rules or expectations—genuine romantic connections require vulnerability, risk, and the willingness to break free from self-imposed limitations.
By the end of the book, both Haleigh and Jack break their own rules, allowing their love to flourish without restrictions.