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If you liked Kanon (2006) add

...then you might like Clannad: After Story add

If you've seen Kanon you know what to expect with Clannad Afterstory and vice versa. Neither of these series are afraid to sacrifice main characters. Both of them have multiple, ongoing story arcs and both of them are quite sad stories until the last few episodes. Afterstory is much more similar to Kanon than Clannad the original series was mainly because Afterstory had much less of a focus on comedy and more on the drama that unfolded after the first series was over.

If you liked Shakugan no Shana add

...then you might like Toradora! add

The main female leads Shana from Shakugan no Shana and Taiga from Toradora were voiced by the same Japanese voice actress (Rie Kugimiya) and have similar character traits. Toradora and Shakugan no Shana are both romantic comedies and for the most part are centered around a male lead and a strong somewhat tsundere female lead (Tiaga *definitely* is) supported by a fairly small group of other characters. Even though Shakugan no Shana is a more combat oriented anime than Toradora, the major difference between the two is for the most part, where and toward whom the inevitable violence is directed. :) In both anime series, the female lead gradually shifts from a more combative somewhat distant personality toward a much more caring affectionate one, at least when it comes to the male lead.