Shadow and Amy

Amy Rose and Shadow have a friendly relationship after having a short, but significant bond.

In Sonic Adventure 2, they interact twice, but each time seems to gain an odd reaction from Shadow. Amy first meets Shadow when she mistakes him for Sonic and hugs him from behind, while Shadow remains still after having been briefly caught off by her launch, and meanwhile, does not shake her off or retort to violence. When Amy senses the lack of a reaction, she releases him, causing him to glance back at her. Amy demands his name when she realizes that he is not Sonic, but he continues to watch her quietly. After Amy notices Dr. Robotnik, she also realizes the mistake she's made, and runs off screaming. During this, Shadow takes a step after her as though to either call or head after her, but simply tilts his head when she is out of range, until Dr. Eggman tells the team that he'll take care of Amy.

Later in the game aboard the ARK, Amy meets Shadow again and this times does her part in helping by begging Shadow to save the world. At first, Shadow simply replies, strangely in a non-threatening way, that it is pointless, but then Amy points out that despite people sometimes being selfish, they were still inwardly good and that saving them was right. Because of this, Shadow suddenly has a flashback of Maria begging Shadow to make people happy. When Shadow comes to his senses he goes off to fight the Biolizard, determinedly and softly telling Amy that he has to keep his promise to Maria...and her.

Amy was also the only one to see Shadow's tear after he remembered that Maria wanted him to save the people that live on Earth (Sonic Adventure 2), making her the only person to see him cry in both Sonic Adventure 2 and Sonic X.. Amy and Maria have the same insight towards humanity, thus this might be one of the reasons Shadow is nice to her, since it's unknow whether or not Shadow remembers Amy's deed in ARK. Amy has also done nothing to earn Shadow's dislike or hate and vice versa, which may be why he's respectful to her... It should also be noted that Shadow is one of the only male characters who does not view Amy as a careless girl, and has been willing, reserved and uncharacteristically soft-spoken to her within the few times they have met. It can also be noted that Shadow likes Amy, but doesn't like Sonic amongst that friendship, in spite of the connections between them, which is also the humor of their relationship. Though, it may be fact that Sonic does not know about the level of Amy's acquaintance with Shadow or the event that she was the one to convince Shadow to assist him with Earth's salvation, either.

During Sonic Battle, Amy shows excitement and concern upon hearing Shadow's survival through Rouge, but quickly becomes angry when Rouge will not allow her to see him.

In Sonic Heroes, the two do not battle, either due to general admiration and respectability between the two despite Shadow's loss of memories, or just because of plotline exclusion...

During Shadow the Hedgehog (video game), Shadow can choose to assist Amy in helping find Cream and have her fight alongside the player during the stage and in the boss battle, but this time, there is no reward in return. During this stage level is the route to an unlockable stage that is titled, "The Miracle of Love" if you allow Shadow to comply to Amy's plea to save the world, which changes the story from dark to hero story, as listed under the, "Unlockable Stage Levels" in the Shadow the Hedgehog Game Guide. This access to the stage is through player's choice and does not affect the storyline. Also, at the end of Shadow The Hedgehog, Amy shows an odd amount of faith and admiration for Shadow, regardless of him being Sonic's arch-rival. When Rouge mutters to herself, "I hope he's okay up there," Amy comforts her with her hands clasped and a cheerful smile on her face, "I'm sure he's fine, Rouge! After all, he is Shadow!"which further displays her positive outlook on the black hedgehog and her general optimism as a character.