The best way to describe Shira Oka: Second Chances to someone unfamiliar with the game style is as a semi "choose your own adventure" kind of game from an American publisher trying to introduce this very Japanese style game play to an American audience. The art style is nothing special and despite being primarily backdrop with little animation from the character silhouettes on screen it manages to lag a little here and there. The game play has quite some depth however as every decision affects somebody someway and you must balance six different skills in order to succeed.
Depending on what you do you make different friends and, potentially, enemies along the way with the end goal to hopefully have a girlfriend by the time you graduate. Don't be afraid to experiment with all the different options along the way, in fact I strongly encourage you to do so. The way the game works is that at various stages you either pass a given event or fail, this doesn't include every event or random encounter but rather very specific plot points and testing points. If you fail or get too many F's on your report card you are sent back in time to start over again, but armed now with the foresight and in game dialogue options of what to do better. The more often you fail, the better your chances are to succeed. In fact the only way to succeed at some points is to fail your attempt the first time so that your character can grow and learn from his mistakes. (Though that's not to say you can't choose to make the same mistake over and over again if you wish.)
There are multiple endings and outcomes, the longer you play the more opportunity you have to grow and reach the harder to get endings. The game rewards your success with experience for your character and sometimes access to cut scenes or background images. The first part is what you want to work for as each point is valuable to your success, the later is just there for the fun, though most of what you will unlock isn't all that interesting to look at. (Each ending does unlock a short video however.)
I enjoy the game, and find the replay surprisingly high for such a simple mechanic. It's basically like being in your own anime with you at the center. I got the game half off and am well pleased with the price, it is up to you if you think it is worth the full asking of $25. (I personally don't think so simply based on the lackluster art.)
Game Play: Click and watch, lots of reading, but with a focus on time management. (3/5)
Art and Sound: Decent, friendly, could be better but does make you laugh. (3/5)
Story: Heart and soul of the game, the reason you play, very nice. (4/5)
Replay Value: Practically the selling point here. Plenty of reason to try new things. (5/5)
Polish: Good, a little bug in the art sometimes. (4/5)