Look Both Ways follows the life of Natalie from the night of her graduation party as the reality splits into two after the different outcomes of a pregnancy test.
Warning: This article contains heavy spoilers
As she is about to graduate from college, Natalie explains her five-year plan to Gabe. He does not agree with her lifestyle and asks her to start living in the moment. They eventually hook up.
On the night of her graduation, Natalie starts experiencing nausea. Her best friend, Cara, brings her a pregnancy test kit. The reality splits into two as Natalie takes the pregnancy test, one where the test result is negative and the other where it is positive.
While the first Natalie is excited to pursue her five-year plan, the second Natalie contemplates her life plans and whether she should keep the baby.
After finding out that she is pregnant, Natalie tells Gabe about it. Gabe promises he will be there for her regardless of her choice. Natalie decides to keep the baby and drives with Gave to her parents’ house.
At the same time, the other Natalie sets on her journey to LA with Cara to explore her career as an illustrator. She applies for a job as an assistant for Lucy Galloway and sneaks into a party to impress her. She meets Jake at the party.
While the first Natalie deals with her job applications, the second one has to confront her parents and their anxiety about the baby and Gabe as a new member of the family.
While Gabe questions his relationship with the second Natalie, Jake helps the first Natalie get a job with Lucy Galloway. Natalie admires her similarities with Jake and a romance brews up between the two.
With the birth of her daughter, Rosie, Natalie starts questioning her life as a mother and her incomplete dreams. The first Natalie questions her job under Lucy Galloway and if it has any future for her.
Both Jake and Gabe help Natalie deal with her crisis. Gabe asks Natalie to move in with her but she refuses as it would be complicated for Rosie and asks him to date new people. In the other timeline, Jake asks Natalie to move in with her and she agrees.
Gabe starts dating Miranda making Natalie conflicted about the new dynamic. Jake leaves for Nova Scotia for a year and halts his move-in plans with Natalie.
The first Natalie presents her portfolio to Lucy who calls her work unoriginal. Upset with the rejection, Natalie calls Jake but they end up in an argument and breakup. Gabe gets engaged to Miranda.
After being heartbroken in both the timelines, Natalie starts working on her illustrations. The first Natalie works on her short movie ‘Indigo’ and the other one works on ‘Night Owl’, a comic inspired by her daughter.
The movie Indigo gets selected for screening at South by Southwest. Meanwhile, Night Owl also gains popularity and the second Natalie is asked to be on a panel at the same festival.
Look Both Ways ending explained in detail:
Does Gabe marry Miranda?
Gabe asks Natalie to move in with him in his new apartment where they could take care of Rosie together but Natalie refuses as it might get too complicated for Rosie if things do not end well. She asks Gabe to date other people.
After being rejected by Natalie, Gabe starts dating Miranda which disrupts their parenting dynamic and increases the complications between the two.
Gabe gets engaged to Miranda and Natalie deals with her heartbreak.
After Gabe’s performance at the South by Southwest festival, Natalie asks him about Miranda. He tells her they broke up as Miranda was not her.
Does Natalie end up with Jake?
After Jake leaves for his work in Nova Scotia, he gets too busy and is unable to make time for Natalie. She is disappointed with the lack of communication and both of them argue. Jake breaks up with her.
Natalie’s ‘Indigo’ gets selected for screening at the South by Southwest festival and she leaves a voice mail to Jake about her happy news.
At the festival, Natalie finds Jake at the entrance of the theatre asking for a ticket. He tells her he fought with people at work to attend the screening and make time for her.
Which timeline was better for Natalie?
The first Natalie sets out on her pre-planned journey to Los Angeles to explore her career while the second Natalie decides to stay home and raise her child with Gabe.
Both of them face challenges on their way to the perfect life. While in the first timeline, Natalie questions her job with her idol, in the other one, she questions her life as a mother. Both of them contemplate how things would have been if they did not choose their current path.
Despite the challenges, Natalie gets recognised for her talent in both timelines and gets invited to the South by Southwest festival.
After fixing their issues with Jake and Gabe, Natalie in both realities, enter the washroom where she took her pregnancy test and whispers, “You’re okay”. Natalie realises that no matter if her life does or does not work out as planned, she will be okay.