ANSWERS: 2
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You really should speak with an immigration attorney, but even if he did gain Canadian citizenship, he'd still be in the US illegally.
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If you get married either in the united or in canada your boyfriend will have to live in canada for a few years (4 years i think) as a landed immigrant first before he can get canadian citizenship. After you get married you will have to sponser him in as ur husband and await approval for his visa to come into canada, from that point he will have to go through the landed immigrant process before he can become a canadian citizen. Not an easy process.
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