Do Lennie and Toby Get Together in The Sky is Everywhere?

Josephine Decker’s teen romance film ‘The Sky is Everywhere’ centers around the grief-stricken world of Lennie, who struggles with loneliness upon her elder sister Bailey’s death. After Bailey’s untimely demise, Lennie confronts the lack of emotional support to cope with her loss. As she fights the hardships of life and grief, she comes across Toby, Bailey’s boyfriend. Their acquaintance suddenly grows into a companionship, as they start to seek comfort in each other. Intrigued by their chemistry, we have taken a detailed look at their intricate companionship. Let us share our thoughts! SPOILERS AHEAD.

Do Lennie and Toby Get Together?

No, Lennie and Toby do not get together. When Bailey died, Lennie’s grandmother and uncle accepted it better than Lennie, who fails to confront the fact that her elder sister isn’t going to walk into her messy room again to clear her bed up. As someone who spreads Bailey’s clothes all over the bed in hope of her sister’s return, Lennie feels isolated in her home and among her friends. As her life moves slowly forward with unbearable grief, Lennie encounters Toby. In Toby, who hasn’t moved on from the death of his girlfriend, Lennie finds herself.

Lennie starts to spend more time with Toby since she is able to share her grief with someone who is aware of its gravity and hardships. She starts to feel a sense of comfort in Toby since she is understood by him. Since Toby can understand the unbearable grief, existential crisis, and emotional heaviness she struggles with, Lennie becomes attached to him. As she becomes aware of the attachment, she realizes that it is built upon the foundation of grief and understanding rather than love. She chooses Joe over Toby because she knows that she cannot be with Bailey’s boyfriend without guilt.

Toby, on the other hand, tries to see Bailey in Lennie. The death of Bailey — who was pregnant with his child — affects him gravely and he tries to find his late girlfriend in her sister. Rather than loving or acknowledging Lennie as herself, Toby is trying to replace Bailey with someone she was most close with. By being with Lennie, Toby also aspires to keep the memory of Bailey alive. Thus, he frequently visits the Walkers to see Lennie. Even when Lennie starts to see Joe, Toby doesn’t stop his pursuit of Lennie, who continues to share her grief with him even while dating Joe.

Lennie and Toby eventually realize that they aren’t meant to be together. Lennie makes him aware that he isn’t pursuing her but his dead girlfriend through her. She also understands that Toby isn’t the way to cope with her grief and her relationship with him will contaminate her emotional attachment with Bailey’s memories. Rather than being with Toby with guilt, she chooses the beautiful life Joe offers to her. When Joe enters into her life, Lennie believes that it is Bailey who is connecting them from heaven and she steps away from Toby.

Read More: Is The Sky is Everywhere Based on a True Story?