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Can he wait with me in Canada if we do Outland? Also, can we do Outland from within Canada?

Thank you so much. The work isn't that important as I can support him. I'm flying down and returning with him one month before the wedding. One reason is that he is a bit shy, and the second is I am hoping I can help vouch for him. Our biggest fear is him being turned back at the border...

Hello, I have proposed to my American boyfriend and he has accepted. YAY! Then we started looking into immigration. He is currently living in Florida, and I live in Ottawa. We would like for him to arrive for the wedding, and be able to stay from that point onward. I can support him while...