It's a US made dating sim. And it's most certainly comparable to the big name Japanese ones (and as I said on Twitter, has far more depth to it than Love Plus which is considered one of the big name dating sims in Japan).
The basic plot is that you're dead beat loser. A not-so-capable angel is then tasked with helping you turn your life around. She does this by sending you back to the start of high school.
The aim then is to make friends/date the people you meet and to better your life within the three years of high school.
Without giving too much away, but as the title suggests, the angel can send you back to the start whenever she deems it necessary, giving you a second chance when you blow it (or when worse happens).
Like most dating sims, you build up your character through multiple choice dialog selections (some timed -- in which options will vanish after a few seconds), and through selecting activities to perform for the week/weekend (these raise your stats).
As for replay value, there are around 10 endings and apparently a true ending that is only available after finishing all other endings.
The only downside to it is probably the voice acting and some small errors in dialog, but you can disable the speech and the small errors don't really detract from the game at all.
Also, if you don't understand the stats all that much, it doesn't really matter. If the angel thinks your having too much trouble, she offers you a one time super boost to your stats which will carry over through all subsequent loops (ie, each time you're sent back, a new loop starts).
While you don't carry the visible stats over (ie, the ones to do with school subjects) to a new loop, you do carry over XP, character stats and character traits.
Also, there's a demo:
http://www.shira-oka.com/play-the-demo.html But seriously, for it's sale price; this is definitely a game worth getting.