Crossing the Border: How it Went

This Canadian made it down & back, but weird question they asked me

As I mentioned in a note to my subscribers, I had an important personal reason to head to the US. So I wanted to share my experience here in this post. This might be interesting to others contemplating crossing, or just curious about what it’s like nowadays. But it is astounding to me that I, as a Canadian, can make this into a post. In any year before, writing about crossing the border would be as interesting as writing about walking Hugo. But here we are now in 2025.

And I will admit I was a bit concerned about this trip. I certainly was not keen to spend my money in the US right now, and of course it crossed my mind that I could be returned or worse, detained, simply for having this Substack account. Or really for no reason at all. But I needed to go and I looked on the bright side in two ways: 1) If anything went awry, I had something to write to my subscribers about! and 2) I know that I am just not important not interesting to the US border people.. Thankfully- or sadly for the content of this story- it was a largely uneventful experience. Just as it has been when I’ve crossed into other dictator-led countries, such as Russia, China and Malawi. I did have one interesting thing occur however which I’m quite curious about now. I’d love your opinion on a question I was asked by the border agent.

My goal was to get to the US, avoid being detained, and avoid being banned on future re-entry. Prior to approaching the border, I put quite a few hours into deleting content on my phone (I had to bring one but I was able to leave my laptop at home). Many recommended a burner phone. But I didn’t have time to buy one and as one legal expert on a news program pointed out, it may very well come across as more suspicious to have a relatively unused phone- where are all my text messages for example?- than to have my real but curated phone with me.

Preparation

Given my Substack focus, it was important to delete this app. As well as delete notes, photos, word files, and texts where lots of my Substack notes, drafts, memes and writings appear. I also deleted WhatsApp where I text with others about my political opinions. However, I also keep a few other social media apps that are run-of-the-mill apolitical to ensure I seemed normal. So I resurrecting my almost-defunct Facebook account and Instagram. Now I am fully aware that if the border agents were motivated, they could detain me and subject my phone to technology that finds deleted content. But I was hedging my bets that I am just not that important and I have the privilege of being an anglo white person.

I always find comfort in odds because in my career I work heavily withs statistics. And odds are almost always extremely low for things that I worry about. For this context, data shows that in June 2025, 1.3 million Canadian residents drove into and returned from the US. Almost all had no issue. Despite all of this however, I was surprisingly nervous.

At the Border

As we approached the border, the lines were relatively short compared to what we are used to. What is often a hour(s) delay was closer to 10 minutes. I had time to count the cars passing through and determined they held each for about 3 minutes per car.

Our officer was professional but very serious. We provided our passports and the officer asked the usual questions. Where do you live? What is the purpose of your trip? How long will you be down? Are you bringing anything that is not going back with you? Yes we said to that last question, for the person we needed to meet.

This apparently was not good. And here is where the questions turned unusual and my curiosity was piqued. They asked, what is the legal status of this person in the US? And I said they were an American citizen. THEN he asked, “and how did this person come to acquire American citizenship?”

We said they were born in the States. And he went back to the computer to write it down.

What? Why would that matter? Since when did that matter? A citizen is a citizen, no? We of course did not ask him.

And we know that Trump has been arguing that not all citizens are the same. In Trump’s mind, those who acquire citizenship through naturalization can lose it if they displease him. And for him, acquiring it through being born in the US might not count either if your parents weren’t citizens.

We were then lectured on US law, which the officer pointed out was the same as Canadian law (lest we think the US was being unfair?): You cannot bring other people’s goods into the US. Fair enough. But he went on and on and I wasn’t really hearing him. All I could think was that we were about to be sent to secondary inspection. That’s not unusual if you live near the border, but in the Trump era I had no idea what that could mean. Is this where they would check my phone?

But then I heard him say, “given how you have answered these questions however, that you are bringing this for a US citizen, I will allow it.”

And a wave of relief rolled over me. We started our car, and drove toward the exit. The exit now has a zigzag of giant orange barriers that are so comically close to one another, you have to drive about 1 mile an hour and concentrate so as not to not hit them with the side of our vehicle.

Over the Border

Once inside the States, I reloaded my Substack, kicking myself I had bothered to put all the work into deleting things that no one cared about. But I had to remind myself it was for insurance purposes: Insurance is bought for peace of mind but you rarely need it and that’s a good thing.

Our visit was purposeful, brief and of course pleasant. Americans are always so kind and friendly. Once I was in the US, it was of course as its has always been. Unless we talked to someone, we couldn’t tell anything was different than before. People walked their dogs, ate in restaurants, and put the trash out. They said hello, they laughed, they loaded their cars with groceries. But it’s amazing how much what is happening in the news can be so invisible in day to day life on the ground. This invisibility is partly why it’s so hard to sustain protests before most people directly experience the terrible consequences of poor political decisions in Washington.

Back to Canada

Unfortunately I knew we might have another slightly stressful experience on the return to Canada. Earlier news had noted the presence of US border agents just before the Canadian exit. Should I delete my app again? I decided to simply hide it from the Home Screen on my phone. Coming back in the early morning, there was no US border agent near the Canadian entrance and we were pleasantly surprised to see no line up into Canada either. We quickly crossed into Canada and felt a deep sense of relief to be home.

So this was my mostly very uninteresting story of one Canadian going to the US for a visit. Sorry it was not more exciting to read (if you got this far), but this was a good thing for me.

Thanks for reading!
Canada Resists