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Number one, no, she probably doesn't. How many people in the states wear kanji on t-shirts and have no idea what it says? Those words are kinda common in the US so people in japan probably think that we think it's cool & good to say. (I love that second picture XD) On the other hand, she might know and just think they're funny. Cuz they are. Those words aren't offensive to non-english speakers, after all.
Number two, i don't have a clue who that is. Doesn't look like nagase but i don't know. *shrug*
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