To Heart, from 1999, is an early conversion of a Bishoujo game into an Anime. The main cast consists of Hiroyuki, the random loser guy that's the protagonist of the show and Akari, his next door neighbor and constant companion, with the potential for much more. There's a strong B cast consisting of the rest of their circle, which includes the class gossip Shiho and other male character/sports star Masashi. As could be expected in a Bishoujo game conversion, there's also a large female supporting cast. Unfortunately, few of the girls undergo siginificant character development.
The 13 episodes of To Heart can be divided into three categories. The first 9 episodes are basically one-shots featuring the girl of the week, the next 2 are the Multi arc, and the last two are the finale.
The girl of the week episodes generally consist of a single girl being introduced with some sort of problem. Hiroyuki (and usually Akari) come in to help her out, the problem is solved, the episode ends, and we don't see much of her again.
The problem with the first 9 episodes is that a single episode is just too short for a character to undergo significant development. So we're stuck seeing a bunch of characters that seem interesting enough paraded on the screen. Any emotional investment we put into these girls of the week is lost, as they only show up again in cameos. I think this is an example of there being too large a cast for the length of the show, and point to Da Capo and Kanon as having done this right, the first by lengthening the show and the second by having a smaller cast. These first nine episodes are only okay, but they could have been made better with follow-ups.
We then have the two-episode arc featuring the maid android HMX-12 Multi, which is the best part of the series. Multi is a robot maid who has been placed in Hiroyuki and Akari's school for two weeks to learn how to interact with humans. She's one of two prototype models who are competing to become the new production model robot maid. The loser will be dismantled at the end of the test. Apart from cleaning, which she excels at, Multi isn't very good at being a maid, so it's up to Hiroyuki and Akari to help her to be better.
(There's actually an interesting discussion as to why people would prefer an incompetent robot made over a super-competent one like Multi's "sister", HMX-13 Serio)
The Multi arc is two episodes long, but they're two great episodes. We have an interesting new character introduced, she interacts with the mains in an interesting way, and once we get to know her they begin dangling the sword of damocles over the heads of the mains. Two episodes is long enough to pull off an interesting, and great story. I think these episodes stand alone well enough that they're probably worth watching even if you skip the rest of this series.
The last two episodes are a reasonably satisfying finale, in which Akari is finally forced to confront her feelings for Hiroyuki. (Who seems to be of the somewhat oblivious type, which is how he can become friends with so many girls over the course of the series, even when all of them have crushes on him.) The finale is good.
A problem with Akari is how willingly she goes along with Hiroyuki's dealings with other girls. While Multi gets placed in the little-sister/not-human bin as not a romantic rival, I wish in the series Akari felt a little less secure and acted more as Hiroyuki dealt with the various girls of the week. (The manga, which is told more from Akari's perspective, handles this better.)
The music and general tone of the series are somewhat melancholy, so be aware of that.
It's hard to rate this series. Overall, I'll give it a rating somewhere between okay and good (pretty good?), and reiterate that the Multi arc (episodes 10 and 11) is great.
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