People often remember their first love with a bitter-sweet feeling and this theme is mostly prevalent in 9 short tales from Kawaguchi Kaiji, adapted into short animations by 9 different directors. The stories vary from touching and nostalgic, to cheeky and fun and some even develop into a rather bitter ending. What they all have in common is the focus on male-female relationship in various interesting ways. You may be surprised to learn, that despite being short, these 10 minute animations tell just as much as a full featured movie, if not even more. Some of them aren't fully developed, so I can't give the movie a 10as a whole, but most of them are quite positive, imaginative and well-crafted. We'll get into details of each animation in a moment.

Sadly, I can't tell you anything about the general directors, art directors, the circumstances or the era the movie was created in, because there simply isn't any information available about it.

It's a shame, really, because besides Kawaguchi's charismatic storytelling, the animation is most of the time also quite intriguing and it would be interesting to know about the work process that was behind it.
I was especially taken aback upon seeing "I Want to Hold Your Hand", and "Let's Spend the Night Together". These two have so few colors, to the point of being monochromatic, and yet they are immensely expressive due to clever animation and fitting soundtrack.
Also, several times an interesting effect appears, when the animation switches to a sequence of photographs, overlapped with cells.

In short, about the 9 stories.
1. "I Want to Hold Your Hand" is named after a Beatles song, which plays in the background through most of the animation and also plays an important part in the story.
A boy wants to win the heart of a tough chick(she loves the Beatles), but is too afraid to even hold her hand and confess his feelings. It's an excellent story and together with music it brings a nice sentimental feeling.

2. "Hero" is all about a couple, once being a part of a high school rugby team, but never confessing to each other. Some nicely animated games in this one.

3. "Let's Spend the Night Together" is absolutely fantastic, even for the lack of colors. The story is incredibly fun, shady and cheeky, as we're following an office guy who gets himself in bed with the girl of a local gangster boss.

The visual expressiveness is excellent. Is it even possible to better express the thoughts of a man, who, after a hot night, is asked by his female partner: "Do you love me?" To which he answers with a quick "Yes", while at the same time the camera shows how he closes the zipper on his pants. Brilliant, I tell you.

4. "Stop the Time" is a bit unfinished(10 minutes is just not enough in this case) and I didn't fully understand the ending. A man returns to his hometown after a long time, just to find his long lost love, who now has amnesia and can't remember a thing.

5. "Betrayal in the City" is another cheeky and clever tale about a man who devises a cunning plan on how to dump his girlfriend. The inner monologue creates a funny atmosphere, even though the theme of breaking up is serious.

6. "I Can't Stop Loving You" is possibly the most average animation in the set, since the story is a bit loose. It tells about a man who has second thoughts before his wedding.

7. "Those Were the Days" is a tad better, but it's also quite unpolished. A mafia boss wants to conquer a really brave woman, who wants none of it. The rough limit of 10 minutes also shows here, since there isn't enough time for deeper story and character development.

8. "Lion and Pelican" tells an interesting story about sacrifice and goodness of a woman, who is determined to support a famous sports star all trough to the end of his career.

9. "White Christmas" is the last tale and one of my favorite in this movie. It's entangled with a warm Christmas spirit, therefore I intend to watch it every year on this joyful holiday xD. What could be prettier than a combination of the famous tune "White Christmas", snowy evening and love (despite all differences).

If you are interested in mature romantic stories and unique animation, you'll love Ai Monogatari: 9 Love Stories. It's not a perfect movie, but it contains some fabulous short animations.