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I worry this date option might be in danger of being cut, because Square's recent iterations of both characters have been cool and macho (with an extra side dish of broody in Cloud's case), with little room for the level of frivolity that such a date requires.But if Square is committed to keeping the bits of rampant goofiness that balance FF7's more serious parts, this scene needs to stay.
Sure, laughs will probably be involved, since we have a hardened soldier sporting an awful pink dress and pigtails to break into a brothel, but the scene also reveals a great deal of important, early characterization.
More than anywhere else, this is where we see Aeris' unconventional thinking come out, as she decides that the absolute best way to rescue Tifa from a bad situation is to dress Cloud up in hastily arranged drag and send him into the fray.
It also shows Cloud's determination and affection for Tifa (whether romantic or friendly, also be funny to see a hyper-realistic Cloud wearing the world's ugliest dress with a straight face. Mister T was all the rage in the 90's, and while allusions to him might hit all our nostalgia buttons, it's going to feel stale this far into the 21st century.
That isn't to say that Barrett has to speak like a proper gent or become a mute main character, either - he just needs a voice that sounds like it belongs to a real person and not a joke from the A-team.
Square-Enix has managed that balance in Advent Children and Dirge of Cerberus, giving him more modern appeal without losing his tough-guy charm.