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Originally Posted by FlamesAddiction
Never dealt with the weed thing, but a friend of mine has a DUI on his record, and it is hit or miss whether they let him across the border apparently.
I went with him to a Red Wings game before and the border agent was nice but made the point that he could be denied entry, but they would let him through that one time. The American border agent also said that if it was the opposite, Canada almost never makes exceptions and any American with a DUI would be denied entry into Canada. Not sure if that is true or if he was exaggerating.
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There are a lot of things they do have discretion with. A dui might not be an issue if it was a long time ago and there were no other convictions on your record. And if you're not driving and can prove you're not planning on driving during your trip it would be less of a concern. There is a weird list of crimes that are never accepted and for some reason dui's are not on that list. But typically you would be denied entry with a dui conviction because it is a public safety concern.
The discretion border officials have with pot is whether to ask you the question in the first place, and whether they should exclude you or allow you to withdraw voluntarily. If you say yes you smoked pot once you're admitting to breaking a federal law but more importantly that the issue has not been resolved legally. There are no circumstances to defend your conviction nor any way to prove you've rehabilitated so it's not an optional matter.
They're not asking because they're curious and they're not asking 80 year old snow birds.