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I am going out with this girl who is, like me, an otaku. We are both beyond being casuals about the sorts of anime that we watch (in other words, we have seen all the major shounen and should titles, like Ghost Files, Knights of the Zodiac, Cardcaptors etc.). A lot of what I watch would probably not be good anime for watching during a date (Mad Bull 34, Wild 7, et al.), so I am just looking at stuff that I can recommend.
So far, I have picrel, Flame of Recca, UC Gundam, plus G, Wing, SEED, VOTOMS, Macross, Area 88, Leiji Matsumoto titles and some CLAMP and Yuu Watase titles.