I fell out of status about a year and a half ago, and I tried to file the reinstament through my University but my advisor suggests i speak with an immigration lawyer to find out what my chances are. Meanwhile I am planning my wedding to my long time boyfriend of 5 years, and my question is. will that help me or make my case worst? and how long after the marriage will i be "legal" again? What should I file?
Aside from the difficulty of reinstatement after so long, your F visa is a "nonimmigrant" visa, meaning that your intention has to be to return to your home country after you finish school. Marriage to a US citizen (assuming he's a US citizen) would not be evidence of that, if anything it may be seen as evidence that you plan to remain in the US.
You should discuss "adjustment of status" (the process of becoming a permanent resident) with an immigration attorney who can review the details of your case, and once you file the necessary applications you can receive work authorization pending adjudication of your application. Once you have work authorization you should be able to return to school - eliminating the need for an F-1 visa.
Again, I suggest discussing the details with an attorney directly. Good luck!
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I think getting your f-1 visa reinstated after one year and a half is going to be very difficult, unless you can show that circumstances out of your controll prevented you from keeping your status. If you marry your boyfriend he can petition for you so you can adjust your status. Consult with an experienced immigration lawyer to evaluate the circumnstances of your case.
While marriage with a citizen will not help you with your F1, it can help you secure a permanent resident card, commonly known as a "green card".
However when going from a nonimmigrant visa to an immigrant status, it is important to follow the process carefully and learn to take appropriate precautions.
I would highly recommend that you and your boyfriend jointly visit an immigration lawyer so both can be on the same page.
Dhenu Savla, Esq.
This answer does not create an attorney-client relationship and is not meant to be relied upon as legal advice.