His and Her Circumstances was overall a very good series, but nonetheless had a few flaws which kept it from being a great one.

Story:
The basic premise of the story (two "perfect" students who end up falling for each other) was very interesting and worked well. However, every once in a while certain segments of the storyline seemed to lose focus or drift off a bit.
Also, there were just WAY too many flashbacks and story summaries, especially in the second half of the series. Trudging through those just wasn't fun, and as always I dock the story vote for putting me through that unpleasantness.

Character:
The characters presented here are excellently put together. There is a large cast of individuals who are clearly defined, distinct from one another, and the chemistry between everyone honestly feels real.

Animation:
Definitely not a pretty show, as the visuals strongly show their age. Still, the creative use of still frames helped along the presentation, and despite the fact that it looks a bit primitive, it still works well for what it's trying to do.

Sound:
Character voices are very good, the english dub is surprisingly strong, and the OP is very well done and really stands the test of time. Actually, truth be told the OP is on the short list of one of my all-time favorites. It just works really well, and it really captures the mood of the series (plus the OP animation was excellent as well)

Value:
The constant flashbacks are irritating, but there are certain segments that are definitely worth rewatching. The first few episodes are great, and scattered throughout the series are a couple spots which really stand out as well.

Enjoyment:
Ultimately, I really did enjoy this series. It felt much more honest than the bulk majority of series, and I really enjoyed almost everything in here. It's too bad that they didn't clean it up a bit more, or I'd really endorse it strongly. As it is, though, it is definitely worth watching, especially if a strong, honest storyline with very interesting characters is valuable enough to you to be willing to sit through a few too many flashbacks and long-winded story summaries.