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Currently you are able to watch "Amagami SS" streaming on HiDive.
There are no options to watch Amagami SS for free online today in Canada. You can select 'Free' and hit the notification bell to be notified when show is available to watch for free on streaming services and TV.
A second-year high school boy finds himself uneasy during Christmas time due to an experience in the past. However, this year at Christmas, he gets his last chance to ask out a graduating female senior named Haruka Morishima — or one of several other classmates. The story of the anime will be arranged in an omnibus format, with each heroine getting her own version of the story animated. Each heroine will sing her own version of the ending theme song.