I have lived in Japan off-and-on for about 12 years. Before I got married (to a Japanese) I was running a harem of four regulars and three semi-regulars. I still game a little when I'm out on my own or with guy friends just to stay sharp and to have the confidence that comes with having spinning plates. I think Skotch and others in this thread have given some great advice, to which I would add the following:
1. Style- Don't worry about trying to match the Japanese on style or fashion. I suggest going with Western classic style instead. I'm talking tweed pants and blazers, waistcoats, driving caps, sweater vests over OCBDs, full-length peacoats in the winter, etc. Of the Japanese, only senior citizens usually dress this way. So, as a foreigner if you dress this way, and dress well, you will really stand out. The women will think you're cool because you look like western characters they see in the movies. Also, dressing this way is much cheaper than trying to match what you see the Japanese wearing in trendy nightspots in Tokyo. Don't go overboard, of course, and try to look too much like Sean Connery. But, find a classic style that fits your physique and face and go with it. I dress this way and get a lot of looks and compliments from random women around Tokyo.
2. Business relationships- Business relationships are really important in Japan, as in most Confucian societies. Most of the time, if you see an attractive female at her work while you are conducting your business, whatever it is, she won't be receptive to you approaching her trying to get a date, because she considers it inappropriate for a work situation. However, if you establish a business relationship with her employer, that will change. This applies to any type of business, be it your local dry cleaner, your neighborhood bar, your landlord's business office, a corporate customer of your company, or the local post office where you drop your mail. Be very professional, polite, and correct the first few times you conduct business with the women working in these offices. Once you start to see a change in their demeanor towards you, such as giving you familiar expressions with their face and eyes, then go ahead and make a bold but polite request to exchange personal information.
You can also use business relationships to benefit you in other ways. For example, my former landlord used to hook me up with baseball tickets the he got through his company. When I was having trouble opening a bank account, he jumped in and got it squared away. If you're going through a dry spell, your business associates/contacts will even try to hook you up with single women, although you should be careful about using this avenue for obvious reasons.
3. Venues- I suggest taking dates to cheap Izakaya. Not only does this save you money, but it actually makes it easier for you to establish intimacy and kino with them. In a regular restaurant it is likely that you will be sitting across the table from them. In an Izakaya, you can sit at the counter or a small table in which you will be right next to them. Izakaya have cheap, fruity alcoholic drinks that girls like to drink like water. You can get out of there with spending as little as $30-$40 for the both of you.
4. Love hotels- As Skotch mentioned, it can be difficult to get a woman to go to a love hotel with you because there is no plausible denial. I've tried to find strategies to get around this and I've found one that works moderately well. As the evening progresses and kino is escalating and she is warming up from it and the alcohol, I casually mention love hotels in passing during the conversation. My comments about them are warmly humorous and positive, nothing negative or pejorative at all. That way, it's in her mind that a love hotel for your situation is no big deal. At the end of the evening when it's time for end game, it should be a little easier to lead her into the hotel. Logistics is important here. You should arrange the evening so the last restaurant or bar that you are in is as close as possible to the love hotel that you're planning on taking her to. Then, of course, as you're walking to the hotel keep talking, joking, and laughing the entire time so her logical mind doesn't kick in.
5. Leadership- As Skotch mentioned, you need to be as alpha, masculine, and in charge as you can be. If your Japanese is not proficient, you may have to depend on the girl for certain things, such as ordering your food. You still need to try to keep as much control as you can. For example, if you're unfamiliar with the area, ask her for a list of restaurants, but then you make the decision as to which one you two will go to. If you're in a cocktail bar and she's wavering on which drink she wants, ask her which ones she is considering and then choose one for her. Most Japanese women love to be in a feminine, submissive role and turns them on to be with a masculine man. They want to be seen with a cool, collected, strong-framed man (but not an asshole, of course). You may be tempted to let the woman take charge because of her language and cultural knowledge. Resist this temptation as much as possible.
If I think of any more advice that no one has mentioned, I will post it here.
1. Style- Don't worry about trying to match the Japanese on style or fashion. I suggest going with Western classic style instead. I'm talking tweed pants and blazers, waistcoats, driving caps, sweater vests over OCBDs, full-length peacoats in the winter, etc. Of the Japanese, only senior citizens usually dress this way. So, as a foreigner if you dress this way, and dress well, you will really stand out. The women will think you're cool because you look like western characters they see in the movies. Also, dressing this way is much cheaper than trying to match what you see the Japanese wearing in trendy nightspots in Tokyo. Don't go overboard, of course, and try to look too much like Sean Connery. But, find a classic style that fits your physique and face and go with it. I dress this way and get a lot of looks and compliments from random women around Tokyo.
2. Business relationships- Business relationships are really important in Japan, as in most Confucian societies. Most of the time, if you see an attractive female at her work while you are conducting your business, whatever it is, she won't be receptive to you approaching her trying to get a date, because she considers it inappropriate for a work situation. However, if you establish a business relationship with her employer, that will change. This applies to any type of business, be it your local dry cleaner, your neighborhood bar, your landlord's business office, a corporate customer of your company, or the local post office where you drop your mail. Be very professional, polite, and correct the first few times you conduct business with the women working in these offices. Once you start to see a change in their demeanor towards you, such as giving you familiar expressions with their face and eyes, then go ahead and make a bold but polite request to exchange personal information.
You can also use business relationships to benefit you in other ways. For example, my former landlord used to hook me up with baseball tickets the he got through his company. When I was having trouble opening a bank account, he jumped in and got it squared away. If you're going through a dry spell, your business associates/contacts will even try to hook you up with single women, although you should be careful about using this avenue for obvious reasons.
3. Venues- I suggest taking dates to cheap Izakaya. Not only does this save you money, but it actually makes it easier for you to establish intimacy and kino with them. In a regular restaurant it is likely that you will be sitting across the table from them. In an Izakaya, you can sit at the counter or a small table in which you will be right next to them. Izakaya have cheap, fruity alcoholic drinks that girls like to drink like water. You can get out of there with spending as little as $30-$40 for the both of you.
4. Love hotels- As Skotch mentioned, it can be difficult to get a woman to go to a love hotel with you because there is no plausible denial. I've tried to find strategies to get around this and I've found one that works moderately well. As the evening progresses and kino is escalating and she is warming up from it and the alcohol, I casually mention love hotels in passing during the conversation. My comments about them are warmly humorous and positive, nothing negative or pejorative at all. That way, it's in her mind that a love hotel for your situation is no big deal. At the end of the evening when it's time for end game, it should be a little easier to lead her into the hotel. Logistics is important here. You should arrange the evening so the last restaurant or bar that you are in is as close as possible to the love hotel that you're planning on taking her to. Then, of course, as you're walking to the hotel keep talking, joking, and laughing the entire time so her logical mind doesn't kick in.
5. Leadership- As Skotch mentioned, you need to be as alpha, masculine, and in charge as you can be. If your Japanese is not proficient, you may have to depend on the girl for certain things, such as ordering your food. You still need to try to keep as much control as you can. For example, if you're unfamiliar with the area, ask her for a list of restaurants, but then you make the decision as to which one you two will go to. If you're in a cocktail bar and she's wavering on which drink she wants, ask her which ones she is considering and then choose one for her. Most Japanese women love to be in a feminine, submissive role and turns them on to be with a masculine man. They want to be seen with a cool, collected, strong-framed man (but not an asshole, of course). You may be tempted to let the woman take charge because of her language and cultural knowledge. Resist this temptation as much as possible.
If I think of any more advice that no one has mentioned, I will post it here.