Awkward Gaming Moment: Cloud Strife in Drag

In an earlier post, I claimed that Cloud Strife was one of the most badass characters in the Final Fantasy games, certainly more so than Tidus and Vaan of later games.  However, there is one moment in Final Fantasy VII that puts this into question, which is when Cloud dresses up in drag.  For all five of you who haven't played FFVII, I'll have you know that I'm not making this up.

In an early mission in the game, Cloud wanders through the Wall Market section of Midgar, collecting items of clothing such as a dress and lingerie, and even finds himself obtaining a wig.  The point being that Cloud needs to enter a mafia leader's house where he believes Tifa has been kidnapped.  Apparently cross dressing is the only way to do this, I guess Cloud forgot that he carries a body-sized sword and is powerful enough to match Sephiroth.

So anyway, Cloudette manages to get an audience with the mafia leader, and if it wasn't awkward enough seeing Cloud in a dress:

Don't worry, because it just keeps getting more awkward...

And more awkward...

Tifa eventually barges in and finds Cloud in this awkward situation, making for one of the funniest parts in the game.  Whether you think it's funny or mentally scarring, we can all agree that this is definitely an Awkward Moment in Gaming!