Repetition can make anything seem normal. Even the most extreme and unfamiliar phemonema can become typical if experienced enough. And yet, sometimes things can remain stubbornly novel, in the best way. My experience with visiting Toronto regularly has aspects of both, and it's been surprisingly fascinating to think about.
For one, I live in Chicago and so visiting means taking a flight. Or technically a long drive, but it's hardly worth losing one day going and another coming back, and so I fly. When I was young flying used to be an entire experience. It might mean waking up early, heading there 4 hours early, wrestling your heavy bags to the check in counter (which are of course filled exactly up to the weight limit) and barely muddling through TSA. And of course, after all that you get the privelege of sitting in a cramped seat for 8 to 12 hours before being faced with customs on the other side.
Admittedly this experience might be a bit warped by being an immigrant. Most travel was international travel to other continents; trips that we'd save up for to go on once a year (or even less). They became a whole ordeal. In constrast, I can see why flying domestically is so much easier and so much more popular. All my intuitions about the difficulty of the airport experience were turned upside down.
American airport security is known for being especially annoying. However it turns out there are ways to bypass pretty much all of the annoying parts. If you sign up for all the optional programs, precheck/global entry/nexus/clear (and it feels like there's more every day) you can essentially skip all the bad parts. No taking off your shoes or grabbing your laptop, no having to go through immigration. Oh, plus taking only a backpack means I just stroll through the airport and onto the plane like I'm catching a bus. No baggage claim at arrivals either.
Here's something that I still find crazy. I can take the train to the airport, and I live only 30 minute away. For visiting Toronto, I also only take a spare pyjama and shirt, since that's what I normally took when I visited people for a weekend. That means if my flight is boarding at 4:30, I can start "packing" at 3:30 and still reach the gate with enough time to buy a small snack. With a flight that's 1.5 hours long the convenience is incredible.
It's also worth mentioning that the arrival airport in Toronto is one of the most convenient I've ever seen. It's on the lake and connected to the heart of downtown with a short, walkable tunnel. I can land, skip immigration, and walk over to my friends condo in about 15 minutes. It's incredible to have this easy access and it's part of the reason I'm quite happy with where I am in Chicago. I genuinely think this may be some of the best non-driving access to another city you can possibly get.
Ok enough about the logistics; what is it actually like? I lived there for 5 years, and still have so many friends and family in Toronto. I usually only go for a weekend since why burn a vacation day when it's so easy to visit, which practically means less than one and a half days of usable time to meet people. And my periodic challenge is to make sure I don't waste any second of those 1.5 days.
I'm not especially social. I don't think I have a ton of close friends, but I do have a lot of acquaintances. There's a lot of people who I would passively run into or meet while going about my everyday life, and we'd get a chance to catch up but not really try to meet outside of that. That's the way I like it, since I consider myself more introverted and don't like an abundance of social plans.
However now that I don't live in Toronto anymore, I won't get a chance to see someone unless I specifically set out time and make a plan to meet. This is especially challenging because I have a lot of widely dispersed acquaintances who don't really know each other, but I still wouldn't want to never see them again. And it's especially tricky when people aren't even super sure about their plans or availability.
So I'm left with the task of cramming in as many meetups and hangouts as I can during one visit. Usually rotating between different groups on different visits to make sure I get them all. Sometimes some close friends and family want to see me more often, after all how could I come to Toronto and not drop by? Other times I devote entire visits to specific groups of people, either spending all my time with my friends downtown or with family in the suburbs.
Sometimes it feels like I get a month's worth of social interaction during those 1.5 days. It can be tiring of course, especially on those days where I stay up late one night with one group and then wake up early the next day to meet another. But surprisingly, it's actually not as tiring as I would have expected, and I often leave feeling strangely fulfilled.
People say absence makes the heart grow fonder, and I never cease to be surprised by how fondly many people remember me. Especially since so many of these people were kind of mere acquaintances who'd I'd hang out with but not grow especially close to. It almost feels like this strategy makes for stronger bonds than before; by planning dedicated meetings and waiting so long between them we always have more to talk about; the intentionality feels valuable.
My social battery is never more empty than after a Toronto trip, but on the other hand there's a part of me that never feels more fulfilled. Not necessarily in a normal way, but for a short 40 or so hours I get to feel like a celebrity. I'm not sure how things will change socially if I ever move back permanently, but I can only imagine it wil have all been for the better.