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The 10 Best Movies Like Look Both Ways

Look Both Ways hit Netflix on August 17th and has already caused quite a discussion since the release of its trailer, pleasing Lili Reinhart fans alongside rom com lovers. This dramatic flick pays homage to its clever title by following Natalie as she suddenly finds her life split into two parallels: one where she discovers she is pregnant and the other where she chases her dream career.

The movie is a highly anticipated addition to the romance genre that encourages viewers to reflect on important life changes and how they can impact one’s future. Here are a few other movies that do exactly the same thing for fans looking for more titles with similar themes and storylines.

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About Time (2013)

Stream On Starz

About Time captivated fans from the offset due to its ability to cater to sci-fi lovers in addition to rom-com fans. This unconventional flick follows Tim as he employs his time-travel talent to woo Mary. But when his dad falls ill, he is met with a heart-wrenching dilemma about whether to stay in the past with his dad or pursue his future family.

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Although About Time doesn’t explicitly show two parallel lives like Look Both Ways, its use of time travel leads to Tim having to choose between two different moments in his life. The movie is one of the saddest but most wholesome romantic flicks and, similar to Look Both Ways, it urges viewers to celebrate every encounter in life, including which path it takes them down.

Waitress (2007)

Available To Rent On Apple TV

Waitress may be an award-winning Broadway musical, but before it moved to the stage, Jenna Hunterson’s story was originally told on the silver screen. Jenna is a pie-making waitress who gets pregnant and battles with planning her escape or continuing her everyday life, with the added excitement of her affair with the town’s sweet new doctor.

The movie is known for its feminist undertones captured through its trio of powerful women who consistently support one another through pep talks of empowerment. Jenna’s love life mirrors the parallel lives of Natalie, as she must either stick with the man she’s always known or go with a man that she could easily fall in love with. And whilst both films are similar, Waitress stays true to its theme of self-empowerment with Jenna’s choice to stay single, in the end.

Brooklyn (2015)

Available To Rent Or Buy On Apple TV

Brooklyn stars Saoirse Ronan in her best character yet as she takes on the role of Eilis Lacey, a young Irish woman who boards a ferry to Brooklyn to find better job prospects. Her time in the big city sees her fall in love with Tony, but upon returning home, she is torn between her old life and the one she made for herself across the water.

Eilis’s character battles with the same predicament as Natalie with her conundrum in the final scene, resulting in many viewers debating whether she made the right decision, even today. The movie is a sweet but sad story about chasing a life that abandons familiarity and instead, provides more independence, which is seen through both Eilis and Natalie as they pursue successful careers.

Knocked Up (2007)

Stream On FuboTV

Directed by Judd Apatow, Knocked Up is largely based on his own experience with his wife, Leslie Mann (who also stars in the film), as they navigate the birth of their first child together. Alison, a successful career woman, finds herself pregnant after a one-night stand with jobless Ben, leaving the pair to navigate through pregnancy.

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Knocked Up follows the same storyline as Look Both Ways and gives viewers a front-row seat as the unlikely couple get to know each other as they come to terms with the idea of becoming parents. The movie offers a comedic view into a life-changing moment and highlights the complex emotions that come with having a baby, especially with a stranger.

Last Christmas (2019)

Stream On FuboTV

Last Christmas is considered one of the most romantic holiday movies, but also contains many important messages between its humor and romance. Aspiring singer, Kate, attempts to return to her old life after a heart transplant, but in a twist of fate, she meets Tom, who subtly helps her embark on a new life of healthy habits.

The movie may have crushed viewers’ hearts with its emotive plot twist that waved goodbye to a romantic ending, but ultimately it left both Kate and fans with a new outlook on what is important in life. Throughout the movie, fans are reminded of how fragile life is, and when one is given another chance, they should always choose the most fulfilling option, as seen in both Natalie and Kate’s characters.

Someone Great (2019)

Stream On Netflix

Someone Great is arguably one of the most underrated Netflix original movies to date, now finding larger fame after being reposted continuously on TikTok due to its powerful messages about growth. The movie follows Jenny as she approaches her final night in NYC after she receives a job promotion which results in the end of her nine-year relationship.


The movie sees Jenny continuously reflect on her relationship with Nate, which encourages many viewers to relate to her desire to stick with familiarity. However, by the end of the film, Jenny chases her career and mirrors the life-changing decision Natalie faces. The movie is celebrated for its depiction of how positive growth can be uncomfortable (also hinted at in the Look Both Ways trailer).

Juno (2007)

Available To Rent Or Buy On Apple TV

Paulie holding Juno's pregnant belly in Juno (2007)

Juno is one movie that fans likely can’t believe turns 15 this year, still earning new fans today and sparking something of a cult following. The quirky flick follows Juno, a teen who finds herself pregnant and faced with many decisions regarding her future, as well as the future of her child.

Similar to one version of Natalie’s parallel life, Juno decides to keep the baby and explores the pregnancy experience whilst also emphasizing the responsibility that comes with raising a child, whether a teenager or an adult, playing into the same dilemma as Natalie’s character.

17 Again (2009)

Stream On HBO Max

17 Again tells the story of Mike O’Donnell who, at 37, finds himself wishing he could turn back time and change some of the decisions he made in high school to improve his life as an adult, but when his wish is granted, it soon changes his outlook.

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Whilst the movie is a comedy, it employs a similar storyline to Look Both Ways that provides viewers with a raw and realistic insight into how people are in control of their own destinies. At first, 17 Again might leave viewers wanting to return to their youth, but it soon sees fans appreciating the life they have, whilst also reminding them that they have the power to change their present but not their past.

Eternal Sunshine Of The Spotless Mind (2004)

Stream On Peacock Premium

Eternal Sunshine Of The Spotless Mind paved the way for other essential break-up movies when Joel and Clementine undergo a procedure to rid themselves of the painful memories of their past relationship.

The movie utilizes a past and present narrative that provides viewers insight into the relationship between Joel and Clementine, whilst being juxtaposed with Joel’s procedure to forget it. Eternal Sunshine Of The Spotless Mind highlights how every decision, relationship, and memory in life has bearing on whom a person becomes, and like Look Both Ways also stresses the importance of these big life choices.

Sliding Doors (1998)

Stream On HBO Max

Sliding Doors is an iconic film and continues to be referenced by fans who refer to themselves as having a “sliding door” moment. The movie follows Helen when her life is suddenly split into two where one version walks in to find her partner cheating and the other misses it by minutes.

Similar to Look Both Ways, the movie envisions two lives for its main character, resulting in many fans debating which would be the better. Helen’s character encourages viewers to think about how their lives can drastically change just by a chance encounter or a late train. Sliding Doors provides viewers with an intriguing yet romantic watch where fans root for Helen to choose the right man as well as the right life.

NEXT: 10 Movies That Will Trigger An Existential Crisis According To Reddit

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