You have been in Equestria for many years now, and in that time you have seen Twilight Sparkle - the first pony you ever met - change a lot. She has gone from being a small-town librarian to being the Princess of an entire nation — which doesn't do your courage any good when it comes to telling her how much you like her.
But it would seem that you have some competition, as one of her guards is also looking to win her over. When you both proclaim your feelings to her at once, she simply responds by setting the two of you a challenge: "I want each of you to plan, and then take me out on, the best date I will ever experience."
The result is something that all three of you never expected.