10 Thought-Provoking Movies Like Look Both Ways | Similar-List

Look Both Ways, which premiered on Netflix on August 17th, quickly became a thought-provoking conversation starter. The film revolves around Natalie, a young woman whose life splits into two parallel paths: one where she embraces an unplanned pregnancy and another where she follows her ambitious career dreams. As the story unfolds, Natalie wrestles with each future—one marked by motherhood and the other by personal success—and we, as viewers, are invited to explore the power of the choices that define who we become.

Lili Reinhart delivers an emotionally rich performance that resonates with fans of romantic comedies and those seeking a more nuanced exploration of life's crossroads. Look Both Ways isn't just about the events that happen to us; it's about our life-altering decisions and how those choices ultimately shape our futures. If Look Both Ways made you reflect on the parallel lives that could have been, you’ll find a rich selection of films in this list that delve into similar themes of life-changing decisions, alternate realities, and the power of choosing one’s path.

10 Thought-Provoking Movies Like Look Both Ways

About Time (2013)

About Time captured viewers' hearts by blending science fiction with heartfelt romance, making it a standout for sci-fi enthusiasts and rom-com fans. The story follows Tim, a young man who discovers that the men in his family possess the ability to travel through time. He uses this newfound gift to win the heart of Mary, the woman he loves. However, when his father falls ill, Tim is faced with an emotional dilemma: should he continue to alter the past to spend more time with his father, or should he embrace the future with the family he’s building?

While About Time doesn’t explore two distinct parallel lives like Look Both Ways, it still grapples with the consequences of choosing between two very different futures. It’s a poignant exploration of how big or small choices profoundly shape our lives. At its core, the film is a reminder to savor the present and cherish every moment, no matter how fleeting. Much like Look Both Ways, it illustrates the beauty of life's unpredictable paths and the importance of celebrating the journey wherever it leads.

Waitress (2007)

Waitress is a beautifully crafted, emotionally rich film that follows Jenna, a talented but unhappy pie maker trapped in a toxic marriage. When Jenna discovers she's unexpectedly pregnant, she faces an impossible choice: stay in the life she knows, filled with routine and unfulfilled dreams, or break free to carve out a new future for herself, her unborn child, and her passion for baking.

Much like Look Both Ways, Waitress explores the crossroads between two distinct lives, each with its challenges and rewards. Jenna’s story is a powerful example of how the most difficult decisions—whether about love, career, or family—often push us to grow the most. The film isn't just about the struggles of motherhood or love; it's about self-empowerment, personal transformation, and finding the courage to choose the life you truly want, even when the path ahead is uncertain.

The movie’s unique blend of humor and heartbreak, paired with an inspiring lead performance from Keri Russell, makes Waitress both uplifting and thought-provoking. Like Natalie in Look Both Ways, Jenna finds herself torn between two versions of the future, and her ultimate decision reminds us that the choices we make, no matter how daunting, can lead to the most profound transformations. Whether you’re seeking to connect with a character’s emotional journey or simply looking for a film that celebrates the power of choice, Waitress is a perfect match.

Brooklyn (2015)

Brooklyn is a poignant and beautifully crafted story that explores themes of identity, belonging, and the tough choices that define our futures. Set in the 1950s, the film follows Eilis Lacey, a young Irish immigrant who moves to New York City for a better life. There, she finds love with Tony, an Italian-American man who represents the promise of a new beginning. But when tragedy strikes back home, Eilis faces a life-altering decision: should she return to Ireland, where her family needs her, or remain in Brooklyn, where she has built a new life and found love?

Much like Look Both Ways, Brooklyn delicately examines the tension between two parallel lives, each offering opportunities and sacrifices. The emotional depth of Eilis’ journey reflects the universal experience of confronting the unknown and making decisions that could change everything. The film portrays the internal conflict of wanting to honor your roots while also embracing the possibility of self-discovery and independence.

The strength of Brooklyn lies in its ability to capture the delicate balance between loyalty to one’s past and the desire to build a future on one’s terms. Eilis’ struggle to choose between staying in the familiar comfort of her homeland and pursuing the freedom that Brooklyn offers is a powerful exploration of personal growth. Like Natalie in Look Both Ways, Eilis’ journey reminds us that life’s most important decisions often push us out of our comfort zones, forcing us to choose between what we know and what we can become.

With stunning performances from Saoirse Ronan and a carefully nuanced script, Brooklyn is a perfect choice for anyone captivated by the idea of choosing between two diverging paths and reflecting on the people we become due to those choices. Whether you’re drawn to themes of love, self-discovery, or the immigrant experience, Brooklyn offers a beautifully layered narrative about finding one’s place in the world and the sacrifices that come with growth.

Knocked Up (2007)

Knocked Up is a comedic yet insightful exploration of life’s unexpected turns, particularly regarding unplanned pregnancy and the challenges of building a future amidst uncertainty. The film follows Alison, a career-focused woman who experiences a one-night stand with Ben, a laid-back slacker with no clear direction in life. When Alison discovers she’s pregnant, the two are thrust into an awkward, sometimes funny, and ultimately transformative journey of figuring out how to make a relationship—and a family—work.

Though it may seem like a lighthearted rom-com, Knocked Up delves deep into the complexities of life-altering decisions, much like Look Both Ways. Both films explore the tension between an individual’s dreams and the unexpected realities that force them to reassess their priorities. Like Natalie in Look Both Ways, Alison is suddenly faced with a fork in the road: continue on the path she envisioned for her career and independence or take on the responsibilities of an unexpected pregnancy and a relationship with Ben.

What sets Knocked Up apart is its approach to the chaotic, unpredictable nature of life’s biggest moments. The film shows how life’s challenges don’t always come wrapped in neat packages, and sometimes, the most meaningful changes happen when things go off-script. While Look Both Ways focuses on parallel paths Natalie might have chosen, Knocked Up emphasizes how life can throw curveballs, forcing its characters to adapt to situations they never saw coming.

Knocked Up also humorously yet genuinely portrays relationships under stress, especially in the context of parenthood. It showcases how, even when you’re not ready for life's big changes, you can grow into your new reality and find joy in the unplanned. The film’s blend of comedy and heartfelt moments makes it a standout in exploring how life’s defining moments often come from those decisions and circumstances we least expect.

For anyone who enjoyed Look Both Ways, Knocked Up offers a perfect balance of humor, heart, and real-life challenges. It is an excellent choice for those reflecting on how unexpected decisions and life events can profoundly shape who we are. It reminds us that, like Natalie’s journey, life’s unpredictable turns may be hard initially, but they can ultimately lead to personal growth and meaningful change.

Last Christmas (2019)

Last Christmas is a heartfelt exploration of second chances, personal growth, and the often unexpected nature of life-altering decisions. The film follows Kate, a woman recovering from a heart transplant who has fallen into a life of self-destructive habits. Her world shifts when she meets Tom, a man whose quirky nature and kind spirit help her re-evaluate her choices and rediscover the importance of living a life true to herself.

Much like Look Both Ways, Last Christmas delves into the idea of having a second shot at life after a major turning point. While struggling with guilt and a sense of lost time, Kate can make different choices—improving her health, embracing love, or changing her outlook on life. Tom’s mysterious influence catalyzes Kate to rethink her priorities, ultimately leading her to confront the pivotal moments in her past and decide what future she wants to create.

The film’s focus on the fragility of life and the power of making meaningful changes in the face of adversity resonates deeply with the themes in Look Both Ways. Both films grapple with the notion that life is full of unexpected opportunities and challenges, and how we respond to those moments ultimately defines us. Where Look Both Ways explores the idea of parallel lives based on a single choice, Last Christmas asks whether it’s possible to start anew and shape a more fulfilling life, even after everything seems to have gone wrong.

Last Christmas also touches on the idea of emotional healing. As Kate struggles with her past mistakes, the film underscores how confronting our issues and taking responsibility for our actions can lead to growth. Similar to Natalie in Look Both Ways, Kate learns that life’s uncertainties and setbacks are part of what makes us who we are. The film offers a powerful message about embracing the unknown and finding hope in life’s most difficult moments.

Last Christmas offers a beautifully crafted story about transformation, redemption, and the delicate choices that can change our lives. It’s a perfect choice for anyone reflecting on the impact of decisions and the potential for reinvention, especially when we least expect it. The emotional depth of the film, combined with its optimistic message, makes it a moving exploration of how we can choose a different, more fulfilling path, no matter where we’re starting from.

Someone Great (2019)

Someone Great is a heartfelt exploration of self-discovery, emotional growth, and the challenging yet rewarding journey of moving forward after a major life change. The film follows Jenny, a woman who finds herself at a crossroads after the end of a long-term relationship with her boyfriend, Nate. As she prepares to leave New York for a new job in San Francisco, Jenny reflects on the relationship that defined much of her adult life and the future she thought she would have. Faced with the uncertainty of her love life and career, Jenny embarks on a wild final night out with her best friends, hoping to find closure and clarity before she makes her next big step.

Much like Look Both Ways, Someone Great explores the emotional rollercoaster of life-changing decisions and the internal struggle between holding on to the past or embracing the future. The film’s exploration of the heartache and liberation that come with endings and new beginnings resonates with viewers who appreciate the themes of self-empowerment and personal growth. For Jenny, breaking up with Nate is not just the end of a relationship—it’s the end of a chapter in her life, forcing her to reassess what she truly wants from her future and what kind of person she wants to become.

The film takes viewers through the highs and lows of friendship, love, and personal reinvention. Jenny’s close-knit bond with her two best friends, Erin and Blair, reminds us that, even when relationships falter, the support of the people around us can help us find the strength to move forward. Jenny's emotional vulnerability as she navigates her pain and uncertainty makes Someone Great a relatable and inspiring story for anyone facing the challenge of change. Whether transitioning from one phase of life to the next, confronting personal regrets, or making a leap into the unknown, Jenny’s journey mirrors many viewers who have had to decide between staying in their comfort zones or taking the risk to pursue something better.

In many ways, Someone Great shares a similar message with Look Both Ways—that growth comes with discomfort, but it is necessary for personal development. Jenny, like Natalie, must learn to let go of her past to embrace a future full of new opportunities. Both films remind us that while our choices can feel daunting, they often lead to unexpected and fulfilling outcomes that help shape who we are meant to be.

Someone Great is a must-watch. It’s a perfect fit for those who appreciate heartfelt, empowering films that explore the intersection of love, career, and self-discovery. The film’s vibrant energy, relatable characters, and uplifting message make it an ideal choice for anyone navigating a major life transition and looking for inspiration to embrace their potential.

Juno (2007)

Juno is a beloved indie dramedy that explores the complexities of unexpected pregnancy and the tough decisions that come with it. At the center of this film is Juno MacGuff, a sharp-witted teenager facing an unplanned pregnancy after a brief fling with her best friend, Paulie. As Juno navigates the emotional turmoil of her situation, she must decide whether to keep the baby or put it up for adoption, all while dealing with the pressures of being a teenager with a rapidly changing future ahead of her.

Much like Look Both Ways, Juno is a film about navigating a pivotal moment in life that forces the protagonist to reconsider her path forward. While Juno’s situation differs from Natalie’s—she’s not dealing with a career vs. family dilemma—her story resonates on the same emotional level. Both films explore the impact of unexpected life events and the responsibility that comes with making life-altering decisions. In Look Both Ways, Natalie grapples with whether to follow a career-focused path or embrace motherhood, while Juno contemplates the responsibilities of parenthood versus the life she could have if she chose to stay child-free.

Juno doesn’t shy away from the complexity of its subject matter. It’s both humorous and poignant, as Juno’s sardonic humor often provides levity in otherwise difficult moments. The film portrays the struggle between being true to oneself and dealing with the expectations of others, especially the adults around her. Juno’s relationship with her parents, the couple she chooses to adopt her baby, and her relationship with Paulie all showcase different aspects of how our decisions ripple out and affect the people we care about. At the same time, the film highlights the importance of community and support, much like how Natalie leans on her friends and family in Look Both Ways as she faces her crossroads.

One of the key themes that both Juno and Look Both Ways tackle is the significance of personal agency and owning one’s decisions, even when they seem overwhelming. Juno doesn’t let herself be defined by her pregnancy; instead, she navigates the challenges with determination, humor, and maturity, ultimately making the right decision for her, regardless of external opinions. Similarly, Natalie’s journey in Look Both Ways shows how taking ownership of her choices—deciding to keep the pregnancy or pursue her career—becomes central to her self-discovery and growth.

The film also highlights the role of relationships in our decision-making process. Juno’s evolving bond with her parents and the adoptive couple reflects the nuanced and complicated nature of family dynamics, while her developing understanding of her feelings for Paulie mirrors the uncertainty of relationships at a young age. Like Look Both Ways, Juno illustrates that life’s defining moments aren’t just about the big decisions themselves but also about how those decisions shape and reshape our connections with the people around us.

Juno offers an insightful and emotionally resonant experience to fans of Look Both Ways, who are drawn to films about critical decisions and the impact those choices have on personal growth. It encourages viewers to reflect on the unpredictable moments that define our lives, the difficult choices we must make, and the surprising ways those choices can lead to greater self-understanding and empowerment.

If you’re looking for a story that balances humor and heart with the complexities of life-changing decisions, Juno is a perfect companion to Look Both Ways. Both films offer a unique, candid portrayal of the decisions that shape our futures, reminding us that even the most unexpected turns in life can lead to moments of growth and clarity.

17 Again (2009)

17 Again is a refreshing blend of comedy and drama that explores the concept of second chances, self-reflection, and the consequences of our choices at different life stages. The film follows Mike O'Donnell, played by Matthew Perry, who is dissatisfied with his adult life and wishes he could return to his teenage years to relive his glory days. Through a magical twist of fate, Mike is transformed into his 17-year-old self (now portrayed by Zac Efron), giving him a rare opportunity to re-evaluate the decisions that led him to his current, unsatisfying reality.

Though 17 Again doesn’t strictly explore the idea of parallel lives like Look Both Ways, it shares a thematic connection in delving into life-changing decisions and their ripple effects. Both films examine how the choices we make—especially at pivotal moments—can alter the course of our future. In Look Both Ways, Natalie faces a fork in the road where she must choose between motherhood and career; in 17 Again, Mike is given a chance to reflect on the decisions he made as a teenager that ultimately shaped his adult life, particularly his marriage and career.

The film’s exploration of youth versus adulthood resonates with the central themes of Look Both Ways. Mike's journey back to his 17-year-old self forces him to confront the idealized version of his younger years, where everything seemed simpler and full of possibility. However, as he tries to fix his mistakes back then, he realizes that his choices—whether in his relationships or his approach to his future—are all part of what made him who he is today. Like Natalie in Look Both Ways, Mike learns that the key to growth is accepting and learning from past decisions, not necessarily changing them.

One of the key elements that 17 Again shares with Look Both Ways is the exploration of how relationships and personal growth intersect. As Mike reconnects with his high school friends, his family, and especially his teenage children, he is forced to acknowledge the impact of his past decisions on his relationships. His chance to "redo" his past helps him realize the importance of being present in his relationships and taking responsibility for how he has shaped his family dynamics. Similarly, in Look Both Ways, Natalie’s choices in both versions of her life—deciding to embrace motherhood or chasing her career—impact the people she loves and her relationships with them. Both films highlight how life-changing decisions are often about more than just personal success; they’re about how those choices affect the people closest to us.

While 17 Again has a comedic edge, especially with the fun of watching Zac Efron play a younger version of Mike, it also offers profound insights into identity and the regrets that often accompany life's big decisions. Just as Look Both Ways reminds viewers that the paths we take are full of unknowns and the weight of responsibility, 17 Again encourages us to consider how our decisions in youth shape the trajectory of our adult lives and how we can take ownership of the choices we’ve made. Like Look Both Ways, the film ultimately champions self-awareness and embracing the future with all its uncertainties.

For viewers who enjoyed Look Both Ways for its introspective look at life-altering decisions and the parallel paths people face, 17 Again offers a fun yet poignant take on a similar theme. Both films show that it’s not the choices themselves but the courage to learn from them and grow that truly matters. If you’ve ever wondered how your life would look if you could turn back time and make different decisions, 17 Again provides a relatable, heartwarming perspective on the power of self-reflection and the possibility of second chances.

Eternal Sunshine of the Spotless Mind (2004)

Eternal Sunshine of the Spotless Mind is a visually stunning and emotionally profound film that explores the complexities of memory, relationships, and the irreversible impact of life’s choices. Directed by Michel Gondry and written by Charlie Kaufman, this mind-bending romantic drama follows Joel (played by Jim Carrey) and Clementine (Kate Winslet), two former lovers who undergo a medical procedure to erase each other from their memories after a painful breakup. However, as Joel relives his memories during the procedure, he begins to question whether erasing the past is truly the right decision.

Like Look Both Ways, Eternal Sunshine of the Spotless Mind centers on the idea that our choices—particularly in relationships—profoundly impact who we are. Both films delve into how life’s pivotal moments, especially those concerning love, can shape the trajectory of our futures. In Look Both Ways, Natalie is forced to navigate the uncertainty of her life’s two potential paths, while in Eternal Sunshine, Joel’s journey through his memories challenges him to come to terms with the decisions he made and their consequences.

The film’s portrayal of Joel’s struggle to hold on to the memories of Clementine, despite their flaws and the pain they caused him, mirrors the central themes in Look Both Ways, where characters grapple with the complexity of making decisions that affect not only their futures but also the lives of others. Both films examine how memories of love, regret, or life’s significant choices define us. In Look Both Ways, Natalie faces the question of whether to embrace motherhood or continue pursuing her career; similarly, Joel in Eternal Sunshine faces the dilemma of whether he can ever truly move forward without losing the pieces of his past that have shaped him.

Eternal Sunshine offers a unique perspective on memory and identity, presenting a scenario where the desire to erase painful memories ultimately conflicts with the reality that those experiences, good or bad, are integral to personal growth. While Natalie in Look Both Ways has to decide which life to lead, Joel must come to terms with how his experiences with Clementine—both the beautiful and the painful—contribute to his sense of self. The film suggests that life’s toughest moments, while difficult, often lead to the most profound personal growth, a concept that resonates deeply with the choices made by the characters in Look Both Ways.

Both films also highlight the unpredictable nature of life and the importance of embracing the uncertainties of the future. Eternal Sunshine takes a surreal approach to explore how we might react if we had the chance to undo parts of our past, but in doing so, it underscores the importance of not erasing the lessons learned through hardship. In Look Both Ways, Natalie’s decision to either become a mother or continue chasing her career highlights the unpredictability of life’s outcomes and how, ultimately, it’s the unexpected turns in the road that shape our destinies.

What makes Eternal Sunshine of the Spotless Mind particularly compelling is its layered narrative structure, with memories being erased in reverse order, forcing viewers to gradually piece together the nature of Joel and Clementine’s relationship. This mirrors Natalie's journey in Look Both Ways, where her choices, while seemingly clear-cut at the moment, are revealed to have far-reaching consequences as her two potential futures unfold. Both films explore how the passing of time and our decisions shape the people we become and how we relate to the world around us.

Like Look Both Ways, Eternal Sunshine of the Spotless Mind offers a thought-provoking exploration of memory, relationships, and the irreversible nature of our choices. Both films suggest that life is a series of interconnected choices, each shaping who we are and who we become. If you appreciate the emotional depth and exploration of life-changing decisions in Look Both Ways, Eternal Sunshine will resonate with you on a deeply introspective level. The film reminds us that our choices—whether in love, career, or personal growth—are part of a larger journey that defines our identities, even when those choices lead us to unexpected and uncertain places.

Sliding Doors (1998)

Sliding Doors is a classic exploration of fate, choice, and the butterfly effect, where one seemingly minor decision can alter a person’s life—directed by Peter Howitt, the film stars Gwyneth Paltrow as Helen, a woman whose life splits into two distinct paths after catching or missing a train. The film follows both versions of Helen’s life, one where she goes on to meet a new romantic interest and another where she faces heartbreak and loss. The result is a thoughtful meditation on how even the smallest decisions can profoundly shape our future.

Much like Look Both Ways, Sliding Doors delves into the powerful theme of parallel lives and the impact of pivotal moments. In Look Both Ways, Natalie’s life is divided into two different realities, one where she faces an unplanned pregnancy and another where she chases her career dreams. Similarly, Sliding Doors presents two diverging outcomes for Helen based on a single, seemingly insignificant choice—whether or not she catches that one train.

Both films examine choice and destiny, showing how life’s most transformative moments often come from decisions we may not even recognize as crucial. In Look Both Ways, Natalie wrestles with the consequences of choosing between family and career, while in Sliding Doors, Helen's experience is a compelling reminder of how a single moment, like missing a train, can send her life spiraling in different directions. Both films highlight how fate, however random, often guides us to a future we might not have expected, with both wonder and regret as part of the journey.

The film also raises questions about the nature of regret and the idea of "what could have been." In one version of Helen’s life, she embraces a new relationship; in the other, she faces emotional turmoil and the loss of an opportunity for happiness. This theme of parallel lives and the contemplation of alternate paths echoes the core message of Look Both Ways, where Natalie must come to terms with the paths available to her and the consequences of her choices. Both films acknowledge that no path is without its struggles and challenges, but ultimately, our choices define who we are.

Moreover, Sliding Doors explores the theme of self-discovery, showing how our choices—whether they lead to joy or hardship—can provide us with opportunities to learn more about ourselves. Helen’s character grows and transforms in each version of her life, just as Natalie’s personal growth is shaped by the paths she considers in Look Both Ways. Both films offer the powerful message that, although we cannot always control the circumstances of our lives, we do have the power to decide how we react to them and how we shape our futures.

What sets Sliding Doors apart is its clever narrative structure. By splitting the story into two simultaneous timelines, the film allows the audience to see how the smallest actions—a missed train, an accidental encounter—can lead to drastically different outcomes. This structure emphasizes the importance of every choice in determining our life's trajectory, no matter how small. Similarly, Look Both Ways uses parallel storylines to highlight how each of Natalie’s decisions shapes the person she becomes and her life's direction.

Sliding Doors offers a profound exploration of the unpredictable nature of life and the transformative power of choice, making it a perfect companion to Look Both Ways. Both films highlight how even the smallest moments can change our lives unexpectedly and meaningfully. If you’re drawn to stories that explore the complexities of decision-making, fate, and the roads we choose, Sliding Doors will resonate deeply with you. The film serves as a reminder that every moment holds the potential for change and that the paths we take, even those we never anticipated, are what ultimately define our lives.

The films on this list, like Look Both Ways, delve into the profound impact of our choices and how those decisions define the course of our lives. Whether it's choosing between love and career, embracing change, or reliving the past, these films remind us of the importance of recognizing the power of every decision.

If you’ve ever wondered about the alternative versions of your life, these films will speak to you. They’ll encourage you to reflect on your pivotal moments and the decisions that have shaped who you are. Like Natalie in Look Both Ways, we all stand at the crossroads of life—faced with choices that can change everything.