Thanks for the replies guys.
@Reikai 1) I wouldn't try to ask someone out just for the sake of the "big date of the year" factor. If you aren't really feeling for someone, but think they might be fun to hang out with, then keep it casual, and do not try to make it work if it goes bad.
Feeling obligated to go out just because of the holiday is baggage you don't need. Going out because you and the other feel like is IMHO the best reason. If you feel like going out on the special day, then go ahead, just don't feel obligated.
2) When I was pursuing women (in long tern relationship now), my opening date was a comedy club. We could have conversation, but if I didn't have anything good to say there was a comedian making her laugh. In movies you can't really talk without being rude to other patrons. I don't know enough about the Christmas date to respond specifically to that.
3) About a week, unless you are worried the special girl might get asked out by someone else first.
1. Not really asking just for the sake of "big date of the year" factor. However, I did think it would be a good time to make a change and actually put effort into getting to know people. I plan on keeping it casual, just going for fun like I said.
2. The comedy club sounds like an interesting idea. In my mind the "typical" Christmas date thing is like... walk through roppongi hills (a place here) to see illuminations:
go for dinner, whatever, then I get lost. lol.
3. One week. Alright.
Hi Reikai, out of interest are you Japanese or just living in Japan? Is the the girl you plan to ask on a date Japanese?
1. Back when I was single a friend and I had what I suppose could be called a dating game. Twice a year, in random locations, we both had to ask out people we liked the look of. Obviously we got rejected by more than said yes but someone always said yes. We explained to the girls that it was just a day out somewhere and it was about having fun more than anything else. It was always a double date which meant that any awkward silences were few. The winner of our game was the person that got a second date. I think that this is the kind of thing you are thinking about and I don't see it as rude or selfish. Instead of approaching it as a date though I would approach it from a point of view of meeting someone new just for a bit of fun and conversation. At the very least you might make a few new friends.
2.Women aren't an entirely a different species think back to your previous relationship and think what made your first date good that time. Personally when it is just for fun as described above then my friend and I always found activity type dates worked well. Ten Pin Bowling, ice skating, dry slope bobsleigh, fun fair, zoo. Fun things to do that allow you to interact with your date. I imagine the only bad thing on any kind of date is long silences or only one of you talking.
3. I think same week is fine.
Its very complicated, but lets just say I'm the closest to a Japanese person that a non-Japanese can get. I'm Asian of Chinese descent, born here, grew up here, speak Japanese, work in a Japanese company, look Japanese etc. However, I don't hold a Japanese passport. People always assume I'm Japanese until I tell them my name (which is a Christian name and rather odd for a Japanese person to have.)
1. Heh, that sounds hilarious! If I can find a friend to do that with me, that would be awesome! This is sort of the thing I'm looking for. I might not have feelings for anyone right now, but perhaps I can use the date to find out.
2. I see. Bowling sounds nice, Ice skating too. The others aren't too available here =p.
4. Additional question: I kind of plan to ask a few girls I know out, just randomly. Girls being girls will probably answer with something similar to "I'll think about it." What should I do at this point? Move on? Wait for a reply?