Chicago, IL

Really fun city. I think the easiest big city in Asia for westerners to feel comfortable in. People are generally pretty friendly on a superficial level, quick to smile, laugh, and help. Unfortunately, becoming real friends with Japanese is much more difficult and most cannot speak English. Store staff are mechanically polite like robots, which is better than rude, but also a bit weird. A bit pricey and gets more expensive after a year of residence (after you get taxed based on previous year's salary, same for health insurance fees). You can drink in public at any time, though it's not really a drinker city like some European cities are known for. Clubs and music events are expensive unfortunately, though quite a few options. Great public transport system, can just be a bit confusing with all of the different names. The street layout is completely chaotic, which can be fun but also disorienting. You will often have no idea which direction you are facing, like you are in a giant maze. You can find most major international food options but not in great numbers. Obviously, Japanese food is everywhere though. It's technically on the water, though odds are you will live more inland. Still, you can reach the bay within an hour or so and an actual beach further south in Kanagawa within 90min. Japan itself has a lot of cool things to check out as well. Best time of year are spring (cherry blossoms) and fall (cooler, leaves changing cooler), though there are a series of summer festivals that start in August that are incredible (people dress in traditional clothes, food vendors all over, tons of fireworks, etc.) and they have a lot of Christmas lights and displays in December. Dating for men is not bad, just don't come expecting every woman wants you. As mentioned before, most cannot speak English and they're somewhat conservative overall, not big on casual sex. You may have an advantage in the dating pool if you're not an English teacher, since most western foreign guys there are and that job is known for not paying that well, and definitely do if you can speak Japanese near fluently. Some negatives besides those already mentioned: it's really humid and mold develops quickly, there are A LOT of crows that creeped me out and cicadas that are VERY noisy in the summer, finding the right specialist doctor that also speaks English can be tricky, the friends you make from other countries come and go constantly, a lot of guys with issues come here (socially awkward, major womanizers, right wing nuts, escaping something from their home country, stereotypical anime fanatics, etc.), Japanese men are not anywhere near as friendly as the women are and are more likely to be xenophobic (pretty much like every other country), living space is really small for the price, vegetable selection is pretty limited and expensive, a lot of food products contain soy, subways get really overcrowded during rush hour, popular areas get really overcrowded on weekends, it's not that English friendly especially dealing with contracts and anything government related (there is a free foreigner help service that can help you via phone and usually whatever government stuff you're dealing with will have at least one person on hand who understands English and can help you).