Senior Member

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Aman:
If an alien [either you, your friend, or whoever "shadowy" person is here] who is physically present in the United States and has entered into the United States with inspection [entered with valid visa or under ˜visa waiver' privilege] will ever file an application for ˜Adjustment of Status' on the basis of marrying with a USC then there absolutely won't be any problem for such alien to have his/her status adjusted even if such alien was/is in the violation of our immigration laws, i.e. working or studying without USCIS permission, or overstaying, etc... All these kinds of ˜immigration-violations' are automatically forgiven if AOS is filed based upon marrying with a USC. This is the privilege Congress has extended to an alien for the sole benefit of USC, which is called- ˜family reunification'. That said, it wouldn't be a problem for your friend to adjust his status even if he would marry his USC-girlfriend after the ˜expiry of his I-94' [being out of status].
However, it's highly recommended for an alien not to marry with a LPR/USC within 90 days of his/her arrival in the United States, otherwise there would a high possibility that USCIS might deny such alien's application for ˜adjustment of status' under the ground of misrepresentation. As entering into the United States on ˜visa-waiver program' or on ˜non-immigrant visa' with pre-immigrant intent is against the immigration laws, and it does constitute a misrepresentation and a fraud. Hence, if an alien were ever found to have misrepresented the govt., then such alien would be barred for lifetime to be entered into the United States. Though there is a waiver available to overcome this bar, depending on an individual's personal situation, but that would still be under the sole discretion of adjudication officer.
At the time of adjusting status, USCIS usually tries to determine whether or not such alien ever has/had any pre-immigrant intent if s/he has previously visited to the U.S. And, the above-said 90 days period is considered as a ˜toll period' to determine such alien's pre-immigrant intent if such alien is seemed to have visited to the U.S. on nonimmigrant visa Therefore, any attempt to try to change the status or even trying to establish a ground (like marrying) to change the status within 30 days of arrival in the United States is considered to have been involved in 100% fraud with pre-immigrant intent. Doing so within 60 days of arrival is considered 70% pre-immigrant intent. And, within 90 days- it's 30% assumption of pre-immigrant intent. After 90 days of arrival, trying to change the status won't be a problem.
The details you have provided about your friend, such as your friend having known his girlfriend-USC for the last 7 yrs or 70 yrs, and that they have met to each other many times in the past, and that they have exchanged phone calls, emails and letters to each other for sometimes, and that they are happened to be from the same country originally, and that they were only friends before but intimacy between them developed later on ONLY after his arrival in the U.S., and that they have finally decided to tie the knot and blah.. blah.. blah... [etc. etc... etc..] are not relevant here, nor these details play any significant role in securing the status ONCE parties are already married.
Good Luck.
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