Okay, so in light of the recently released "Chuunibyou demo Koi ga Shitai!" anime, I'm beginning to get interested in manga that may deal with similar premises.
Anything to do with a character trying to hide an embarrassing or shameful part of their past, but it keeps getting brought up in some way.
Space Brothers - Although very brief, the main character of this story seeks employment, while trying to hide the fact that he was fired from his last job.
Aoi Destruction! - The fifth chapter is an independent story about a popular ladies' man who is trying to hide his otaku phase that he went through as a middle-schooler.
Kakumei no Hi - protagonist finds out he's actually female (intersexed) and drops out of school for a year to undergo a "sex change"... comes back and is utterly embarrassed when it comes to anyone finding out she had been the boy who dropped out