Shadow and Amy first met in Sonic Adventure 2 when Amy hugged Shadow from behind, as she thought that he was Sonic. Shadow seemed more amused than angry, and did nothing to stop her - the moment was broken when Dr. Eggman turned his cannon on her. At the game's end it was Amy who convinced Shadow to become a hero. She was also the only one to see Shadow crying after he remembered that Maria wanted him to save the people that live on Earth.
In Sonic Heroes, Team Dark did not confront Team Rose directly, so they don't fight each other as opposed to Team Sonic fighting the latter. The two teams met at the end of the game, where they teamed up with Team Sonic and Team Chaotix to defeat Neo Metal Sonic.
In Sonic Battle, Shadow and Amy did not fight at all, partly due to Shadow spending most of the game recovering.
In later games, Amy has shown an odd amount of faith and admiration for Shadow, regardless of him being Sonic's arch-rival. In Shadow the Hedgehog, when Rouge expresses concern for Shadow following the destruction of the Black Comet, Amy reassures 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 admiration of him.
Pre-Super Genesis Wave
Amy Rose has shown to be somewhat fond of Shadow, having an unusual amount of faith in him when he seems to lack faith in himself. Being a somewhat equally willed person, she tends to help Shadow regain sight of his purpose, and keep him in check. More than once she has realized the good in him when others failed to.
Post-Super Genesis Wave
Shadow and Amy's past interactions happened roughly the same way as they did in the games. At a later point, Shadow, along with the rest of Team Dark, reluctantly teamed up with Amy and Knuckles the Echidna to go look for Master Emerald shards. Amy teased Shadow, pointing out that he was just jealous that he had to work for G.U.N. while Sonic saved the world, to which Shadow smiled slightly in admission.
In another time, Shadow, Rouge, and Omega teamed up against Amy, Blaze and Cream to find the Sol Emeralds. They fought at first, with Shadow taking Amy out with a single blow of her own hammer (having been given orders by Rouge). Due to the angle he was drawn at, it's impossible to know how he felt about this, but after she recovered Amy convinced him that he had promised to save Mobius, so why not help protect other worlds. Shadow took this to heart and later ordered Rouge to hand over the Sol Emeralds.
Shadow and Amy's first meeting is identical to the games: in "Sonic's Big Break" Amy mistook Shadow for Sonic and hugged him from behind, and he smirked at her without comment. However on the Space Colony ARK, it was Chris who reminded Shadow of Maria, as Amy was not on the ARK at the time. Even non-ShadAmy fans were frustrated by this change, pointing out that it was only done so that Chris would have a part in the Sonic Adventure arc of the series.
In the first part of "Eggman the Video Game" of the television series, Shadow called out Sonic to fight him. After an initial confrontation with Tails and Knuckles, Amy and Sticks charged towards the edgy black hedgehog. Shadow grabbed hold of Sticks' staff, spun it and its wielder, and threw them aside. He then dodged Amy's hammer and kicked her in the face. Both girls surrounded him on both sides. They charged at the hedgehog, but he was able to teleport in time and reappear behind them. Shadow took them both up into the air and dropped them to the ground.
Shadamy has a rivalry with Sonamy (for Amy) and Shadouge (for Shadow). However despite having to be the primary rivalry for both of them, it is still a very popular ship in its own right in fan art and fan fiction.
Common rationalisation is that Sonic is too free-spirited to be tied down to Amy, who often talks about having a family, while at 12, Amy is too young to differentiate love from friendship, so when she grows up she will become interested in a man with a more serious and steady outlook on life.
Some fans theorize Silver the Hedgehog as a son of Shadow and Amy in the future.
- Amy/Shadow tag on AO3
- Amy/Shadow tag on FanFiction.Net
- Shadow/Amy tag on FanFiction.Net
- Shadamy stories on Wattpad
- shadamy tag on DeviantArt
- amadow tag on DeviantArt
- shadowxamy tag on DeviantArt
- amyxshadow tag on DeviantArt
- shadowamy tag on DeviantArt
- shadowxamy-love fanclub on DeviantArt
- ShadAmy-Shipfest fanclub on DeviantArt
- Shadamy-United fanclub on DeviantArt
- The character Shadamy from OK K.O.! Let's Be Heroes is a blatant reference to this ship; a tweet by ianjq tells fans not to "mess with her OTPs".
- Shadoumy - the polyship between, Shadow, Amy, and Rouge the Bat
- SonShadAmy - the polyship between, Shadow, Amy, and Sonic the Hedgehog
- SonShadSilvAmy - the polyship between, Shadow, Amy, Sonic, and Silver the Hedgehog