I do not know why you are not responding, but you are not charged per question, per response, nor per answer. So after I give you my answer, you can continue to ask me questions without additional charge until you are satisfied. I apologize if it is a site issue that you posted and the post did not go through.
Once your friend is out of status even one day, all doors to fixing his status through employment, investment or study are closed to him unless he leaves the U.S. and in your friend's case, because he has overstayed longer than 180 days, it is a 3 year bar meaning when he leaves, he cannot come back for 3 years unless he gets a very hard to get visa. If he reaches 1 year on October 21, it is a 10 year bar. So what can he do? Well, he has the following options:
1) Wait for the immigration reform that comes out. If it is approved the way that they are intending, then he may be able to get Residency if he entered the U.S. early enough.
2) Apply for Asylum (he had to have done this within the 1st year of being in the U.S. unless there is a credible excuse or changed country conditions), Withholding of Removal, Convention Against Torture, or Cancellation of Removal. The first three things are if he fears to return to his home country because he believes that he will be specifically targeted due to his race, religion, nationality, social group or political opinion and that he runs a high risk of great bodily injury, torture, or death as a result. The last, Cancellation, he would have to prove that he has at least 10 years in the U.S. AND he must also prove that if he is deported, a U.S. Citizen or Lawful Permanent Resident that depends upon him will suffer exceptional and extremely unusual hardship. This hardship must be something more than emotional separation hardship or financial hardship, so it is difficult to get.
3) If he marries a U.S. Citizen (for love, of course), he could file for Residency without having to leave the U.S. and the same if he had a U.S. Citizen son or daughter over 21 that filed for him.
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