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scylla said:
You take take a maximum of 90 days worth of medication with you when you enter Canada. Beyond that, the medication would need to be purchased in Canada. As previously explained, as a visitor in Canada - you will have no health care coverage and will have to pay for everything on your own. Even once you are a PR and have health care coverage, it's quite likely your medication will not be covered unless you or your spouse work for a company that provides additional coverage for medications (not all employers do).

An exclusion order bans you from entering Canada for a year.

Sure, you can enter Canada for 2-3 weeks and then leave. However you can't just keep leaving for a day and then re-entering over and over again. Sooner or later this will upset CBSA since you'll be behaving as a resident.

I don't plan on leaving for a day and then re-entering. I can't afford to drive how-ever-many-miles and then drive again, then show up again and go back. When I say keep it to short visits, I meant, go down there, stay 2 weeks, then leave and return home to U.S., stay home in U.S. for a while, then go back at some point.

That being said, I'm not exactly sure how much time I should allow pass before visiting Canada again. 4 months? 3 months?...

Also, will I need to specify at the border that I am visiting a friend, or a boyfriend? Curious as to how that would affect things...
 
You can say your are visiting a boyfriend but make sure you only pack for 2 weeks. That is fine. However, if you show up with winter clothes in the summer or show up with a U-haul, they will get suspicious.
 
Thanks for the answers everyone :) I have a question about laptops - Later on, however long down the road, when everything else is settled, what about when I finally do make the move and have to bring my laptop across the border? How common is it that electronic checks are done? What is that like? Does anyone have advice on this? My computer has stolen music on it. Should I just get a new clean hardrive? or something??? thanks :)
 
I haven't traveled with a notebook much but when I have, they haven't yet checked what is on it. At the most, I have had to power it up to show that it is actually a notebook and not something else.
 
searchingforchange said:
Thanks for the answers everyone :) I have a question about laptops - Later on, however long down the road, when everything else is settled, what about when I finally do make the move and have to bring my laptop across the border? How common is it that electronic checks are done? What is that like? Does anyone have advice on this? My computer has stolen music on it. Should I just get a new clean hardrive? or something??? thanks :)

I carry my laptop in and out of Canada while I was an international student and I was never checked.

Even if they check your laptop (it does happens) I don't think they are too concerned with pirated material, they are looking for child pornography of some sort.
 
it's hard to tell the age of what the people are sometimes, I look on tumblr for it, some of them look young... kind of worried how it would look to a border police, i don't know
 
searchingforchange said:
sadly i look at hentai a lot. i am afraid some of it looks youngish. I'm kinda worried.

Since hentai is basically cartoons (sexually explicit, but still cartoons and not real), it is likely that it will not be an issue. But if you don't want to chance it, then delete it.
 
https://www.youtube.com/results?search_query=Border+Security+Season+2

please watch the above episode videos/shows of CBSA.. it will help you figure out the actual procedure of what's really happening when crossing the border. Good Luck. you will learn a lot from here.