This is the problem with the US Immigration. Should you be out of status even for just a day, then it is construed as being an illegal alien, and thus, laws pertaining to illegal aliens apply. The law does not discriminate whether you overstayed for one day or one year, even if you were under financial difficulties. Let this be a grim reminder that under no circumstances should you overstay in the US, as this will have lasting results on the person's record.

As for a solution to your situation, it would be best at this point to consult an immigration lawyer. I don't know where you're from in the US, but there was a good one I spoke to before, and he is based in Arlington, VA. I could email my uncle to get contact information if this should prove useful for you.

But defintely seek competent legal advice, as your boyfriend's reputation, in the eyes of US Immigration, is already tarnished. I'm sure there is a way through the legal loophole.