Fluttershy invites Discord to help her decorate Twilight's castle for a romantic Hearts and Hooves evening celebration. He agrees without thinking it through, but after his acceptance he realizes there's something else he needs to contemplate...

Fluttershy and Discord have been best friends for years; they've been more than best friends. But lately, Discord has seemed distant, while Fluttershy desperately wants to be intimate with him. The little time they do get together always seems to be interrupted by one crisis or another. She finally decides to invite him to her parent's house for Hearth's Warming, but does not anticipate all the things that could go wrong. Will she ever have some time alone with him? And even if she does, will Discord even care?

The road to redemption isn’t straight, and it isn’t downhill. Princess Celestia has asked Fluttershy to try and reform Discord through occasional visits to his prison chamber, and both his and Fluttershy’s lives connect and diverge through the relentless passage of time. And perhaps Discord can see the distant glimmer of a better life... if only Fluttershy were in it.

Fluttershy has only ventured out on Nightmare Night once, and decided never again. That is, until Discord invites her to a Nightmare Night party in his realm. He assures her by invitation and in-person that nothing scary whatsoever will occur, but it IS Discord. With their mutual friends along (and a few other surprises), will Fluttershy make it through the scariest night of the year?

Discord is near death and as curmudgeonly as ever. When his descendants are dropped off at his home to visit for Hearth's Warming Eve, he is more interested in distracting them so he can sleep. To keep them occupied, he shows them a strange crystal shard he's kept for many years, and is pulled into telling a story about his past that he had tried so hard to forget.

Taking place just after the season 6 finale, Discord and Fluttershy go to Fluttershy's cottage for a little relaxation before parting ways. Discord is somewhat confused by his "waking up" to the fact he probably loves Fluttershy, and is not sure if he should tell her or not.