Okay, I've got one:
What's the most ambitious thing you've ever done in shipping fanfiction?
For me, it was writing a fanfic involving Batman. Okay, it was a drabble, and I used The Brave and the Bold's Batman, but I think I should get points for attempting to pair him with Red Tornado. No matter the incarnation, Batman is one of, if not the most iconic superheroes of all time, and it's hard to characterize someone so well-known without feeling like you committed a mortal sin. Still, I like to believe I at least captured Tornado to an admirable extent. When I'm done with this post, I'll try to track down that drabble and link to it here so you can judge for yourself.
I do, however, hope to top that in a big way. Now, any Fairy Tail fan knows Lisanna had feelings for Natsu before being sucked up by the Anima, which of course pisses of the hardcore NaLu fans. Well, what I hope to accomplish is, put simply, pair Lucy and Lisanna together. Of course, I'll have to watch my characterization very carefully for both characters, since we hardly know anything about Lisanna up to this point, and I need to explain Lucy's lesbianism in a way that makes the reader believe that there is, in fact, a chance that Lucy and Lisanna could end up together in canon. It's tough work, but it will all be worth it in the end, and hey, I'm putting aside plans to start a Let's Play of FireRed for the sake of this fic, so I had better put in the extra effort!
Pokemon Y Friend Code: 3282-3535-2249
Friend Safari: Pansage, Petilil, Gogoat
As of now, my focus is on Safaris with starters (barring Wartortle and Quilladin), but give me your Safari anyway. Chances are I'll find something interesting.