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From what I have seen the answer would actually be a yes. Shadow is very hard to read at a glance but if you pay really close attention you will see aside from Maria who was his closest friend you will see that Amy is a person he does have a bit of a soft spot for. As far as Amy x Shadow x Sonic it is a love triangle but though Sonic really does care for her through all the years and all they've been through together it just doesn't seem he has romantic feelings for her. From what I have seen Amy likes both boys she likes Sonic more because she has known him longer and I don't think she realizes how deeply she could care for him.

- Legendary Yosho

Is shadamy ever going to happen or are they stuck as close friends? Im asking because they have their moments alot in a few games and plus sonic doesn't like amy that way so amy has to give up at some point. Maybe not who knows what she will do. Who knows what shadow will do next. -ZNC ARTZ

They haven't had loads of interaction, there's only two games I can think of where the two talk, of course in Shadow the Hedgehog, Amy does look towards Shadow with admiration at the end of the game, and I think in Sonic Battle, Amy gets excited when she discovers that Shadow's living in Club "Rouge", it's possible that Amy has some feelings for Shadow, perhaps due to some similarities he shares with Sonic, also, chicks dig brooding loners and bad boys. Something that's really interesting is one of story names in Shadow the Hedgehog; if you complete all dark missions, but change to hero missions when you reach Cryptic Castle, you get a story called "The Power of Love", or something similar. However, IMO I think Shadow is far too serious and focused on other things to really think about women or relationships, and I think Amy chasing Sonic is an integral part of the series and something that should not change. Myself 123 21:46, November 1, 2012 (UTC)

Oh dear Aurora, we may wanna close this asap. Shipping is "Serious Business" after all.--Kagimizu-Seeya 'round 21:49, November 1, 2012 (UTC)

I think we're safe for now, perhaps if things get too heated, then we should close it, but for now things are fine. Myself 123 21:55, November 1, 2012 (UTC)

No, because Shadow has too many things to do and I honestly don't think Amy will ever stop chasing after Sonic. She may see him as some sort of acquaintance, but you can bet your top dollar that if she saw Shadow hit Sonic or something like that, she'd go bezerk and clobber Shadow with her hammer. Ivy the cat =) 01:18, November 2, 2012 (UTC)