Originally Posted by
The Drunkard Kid
As the title says, Twilight's Bella Swan vs. Futurama's Phillip J. Fry the first.
1) Arena fight, before either gets any powers
2) Arena fight, vampire Bella vs. Fry with Super Cream. If he gets stomped, also give him a hundred cups of coffee right before the match starts, or the Robot Devil's hands, or his space tapeworms, or whatever combination may be needed to give him a decent chance.
3) They are trapped in a moderately difficult escape room and have to get out legitimately before the heat death of the universe.
4) They go on a date.