Raven and Shaw were in a relationship. It is shown a lot when Raven tells Paxton that she will fly the ship to save Shaw's legs. In "Sanctum", they have a brief sexual moment before Shaw heads to the ground. When Raven finds out Shaw was killed by the radiation towers, she breaks up in tears.
Shaw and Raven first meet indirectly in Pandora's Box. Raven locks Shaw out of Eligius IV's security system. He immediately recognizes her genius and when she flips him "the bird" (text art of a bird), his response is, "Real cute."
They officially meet in Shifting Sands, when Shaw helps Raven by allowing Murphy to escape Shallow Valley. He additionally hacks the missile system preventing Diyoza from killing Wonkru.
In Acceptable Losses, Echo meets up with Raven and explains Monty's plan to take control of Diyoza's satellite from the inside the ship using Monty's flash drive. Raven likes the plan and tells Echo that they can trust Shaw to help them gain access to the ship. During Karina's funeral, Raven asks Shaw to help her get a job working at the ship but Shaw declines. Raven confronts Shaw for not standing up to Diyoza but then Shaw tells Raven about how as a kid he watched Diyoza lead the rescue after the Battle of San Francisco on TV. He tells Raven that Diyoza is not as bad as she thinks and that he is not as good as she thinks. At that point, he storms out, making it clear that he won't help Raven.
Echo suggests a plan to use Shaw's treason so that Raven can get access to the ship. Raven refuses because she would be betraying Shaw, the only person who she could count on. Against Raven's wish, Echo ratts out Shaw as a traitor. She tells Diyoza that Raven can prove that it was Shaw who disabled the missiles if she accessed the ship's computer system. Raven grudgingly complies with Echo's plan. Later on, Raven watches as a brutally beaten Shaw is brought into the church by the other prisoners. She feels guilty that Echo pushed her to betray Shaw like this.
In How We Get to Peace, Echo suggests to Raven that they should kill Shaw. Since Raven is the only other person with Shaw's skills, she would then be put in charge of the ship, which could be their way to victory. Raven doesn't like the idea. Raven is willing to do whatever it takes to save Abby and her people from Diyoza. So, she gives Echo a promise to never let Shaw suffer. Raven then talks during which she reveals that her mother died because of her alcoholism. Shaw comforts her and they share a moment.
In Sic Semper Tyrannis, at the valley, Murphy, Emori, Raven and Echo brainstorming on how to escape. Echo brings up her plan to kill Shaw so that Raven can become the pilot and use the ship against the prisoners. But Raven tells them that Shaw could be useful to them as a spy. She comes up with an idea to divide the prisoners through infighting. While the prisoners are fighting, Raven and Emori would then quickly disable the collars from their people and escape. Raven asks Shaw to come with them, Shaw refuses because he is the pilot and if he runs away with them, Diyoza and McCreary won't stop looking for them and he tells her he cares about her, Raven smiles but she threatens him. So, Shaw agrees to let them take off his collar.
Just before they escape, Kane comes in and tells them that they have to save Diyoza. He tells them about the peace plan he initiated between Diyoza and Clarke, as Raven, Emori, Echo and Shaw escape into the woods. McCreary wakes into the transport ship and declares that he's taking over the leadership. He orders his people to hunt all the traitors especially Shaw, Raven and her friends
In The Dark Year, Raven with Shaw and Murphy, Emori, Echo, Kane and Diyoza are hiding in a cave, They notice that McCreary has called off his people from hunting them and is moving them to strategic positions. They realize that McCreary knows Wonkru is coming. They figure out that Clarke must have betrayed them to McCreary. To figure out a way for Wonkru to enter safely, the Spacekru leaves the cave and starts scanning the area. Raven urges Shaw to remain behind so that he doesn't get captured and tortured by McCreary to launch the missiles. After noticing McCreary's ammunitions, Murphy suggests stealing it, leaving McCreary without weapons. Unfortunately, they're confronted by McCreary's people with more deadly weapons. Just before Spacekru surrenders, Shaw shows up and gives himself up. He tells McCreary's people that they would probably get a big reward if they take him because he's more valuable to McCreary than Spacekru. They are convinced and let down their guard. Shaw grabs the opportunity to attack them, knocking them down within seconds. Spacekru then jumps in to help Shaw in the fight. After that Raven seems disappointed. Later in the woods, Raven reveals that she was only mad because Shaw risked his life and made her worry about him. and they shared their first kiss.
In Damocles (Part 1), After realizing that they've been betrayed by Diyoza and Kane, Spacekru and Shaw radios the people of Wonkru who are in the Dead Zone to speak to Bellamy. Echo asks the remaining Wonkru to come back and fight; but Monty says they won't come because they're disheartened and there's no leader left that they can follow. So, Echo decides that they must go in and give them a leader. She asks Raven and Shaw to come with her. While Madi and Clarke sleep in the church so that Abby can have some alone time with Kane. While Madi is sleeping, Echo, Raven and Shaw sneak in and grab her. Whispering, Echo asks Madi if she's the true commander and if she wants to go lead her people. Madi readily accepts and asks Raven to turn off her collar off before Clarke comes in and askes Shaw to light. Suddenly, Clarke walks in and points a gun at Raven and Shaw to leave Madi alone. Raven calls out Clarke for betraying them. As Clarke insists on shooting them, Echo asks Shaw and Raven to stand down. McCreary has been listening through Clarke's radio the whole time. He comes in just before they can escape. He orders his soldiers to take Shaw and Raven to the transport ship so that they can launch the missiles. McCreary intends to torture Raven until Shaw agrees to launch the missiles, killing all of the remaining Wonkru. So, Shaw begs Raven to activate his collar and electrocute him to death so that he won't have to bomb Wonkru. But Raven refuses to kill him.
In Damocles (Part 2), at the transport ship, McCreary is torturing Raven and Shaw hoping one of them will break and fly the ship to launch missiles on Wonkru. They hold on strong but when McCreary threatens to cut off Shaw's leg, Raven breaks and agrees to fly the ship. Just before Raven begins to launch the missiles, Clarke arrives and threatens to kill Diyoza and McCreary's unborn baby if McCreary doesn't order his men to stop. On realizing that his men have been defeated by Wonkru, McCreary says that he would rather destroy the valley with hythylodium than let anyone else have it. He then asks Shaw to fly the ship to safety before the hythylodium hits the ground in 13 minutes and destroys every living thing. Clarke pretends to be on McCreary's side by ordering Shaw to fly the ship while pointing a shock collar remote threatening to fry her. After counting down to 3, she electrocutes Raven, knowing that Raven would be smart about the situation. Raven grabs McCreary, giving him most of the shock, and Shaw takes McCreary's gun, shooting the other Eligius prisoners in the room, as Clarke kills McCreary.
As they watch Earth burn from a safe distance in the ship, the survivors arrive on board the Eligius IV. During the meeting, they brainstorm on how to survive until the Earth is habitable again. Shaw points out that, based on hythylodium's half-life, it will take at least ten years for Earth to be habitable again. So, both Shaw and Raven propose using the cryogenic chambers that kept the prisoners alive for hundreds of years. Raven praises the cryo technology and says that they would go to cryosleep and wake up ten years later, looking the same age. Madi accepts their suggestion.