#classicaljoy

On Maestro's end:

I think when Maestro saw Emily with the present baskets he thought it was "a cute but meaningless gesture" initially-

Second time he sees her show up at Vox's party, although he's focused on the fact Vox is hypnotizing his employees… he's tickled by the fact Emily believes in the goodness of the overlords sitting at the table (but is perhaps slightly jealous that Zeezi, Prick, and Hatchet got the attention instead- I imagine he can be petty like that)

Tries not to concern himself, but perhaps feels the slightest bit of guilt when Vox throws Emily into a chair and is awkwardly sitting next to the music overlord

Perhaps in the midst of Charlie, Vox, and Alastor bickering and ruining the party, Maestro passes a few glances over. He's rightly confused on what to do.

Seeing Emily save other sinners, damage her own wing, and sing while trying to stop that weapon is when the full-on crush starts on Maestro's part.

Viv confirmed that every sinner (except Alastor, funny that) was impacted by Emily's kind actions, so I think while Emily recovered, she was sent some presents from various sinners including Maestro… probably sent something cheesy and traditional, like flowers and wanting to hear her voice again.

He is not very good at his feelings™, so perhaps he accidentally comes off as arrogant when he writes a letter of gratitude and starts worrying how Emily might interpret it.

Although Maestro prides himself as the "strong and silent" overlord, he is very much easily flustered due to the era he most likely came from. Bro died a virgin in his 50s.

On Emily's end:

The VA for Emily confirmed that she has "high standards", and is normally able to wingwoman other relationships but struggles to find her own- so most sinners who aren't trying or are too far gone are on a no-no list!

That being said, Emily also believes in the goodness of EVERYONE, so the second she realizes Maestro is the "quiet one who scoffs at stuff but wants to rest and doesn't partake in violence much anymore"?

Neuron activation, she is gonna try to find this man's inner goodness… and if not, then he's still a hot older gentleman I mean what

A combination of "I can fix him" but also "whatever is wrong with him is kinda attractive even though I shouldn't think that!"

She tries to get through to Maestro and just knows that he can be redeemed, but is careful not to push Maestro's boundaries. Emily knows she overwhelmed Sir Pentious by accident, one thing at a time

Emily tries to bring out Maestro's better qualities, making him a little less passive-aggressive to his employees and servants, asking him about his passions and music compositions

If she can't have him, then Emily will absolutely try to play shipper on deck and see if Maestro likes anyone! (clueless girl doesn't know it's her-)

As a couple that's dating:

Although they both like music, they have… different tastes, but are open to one another's preferences! (Even if Maestro can be a little bit of a snob at first)

Emily actually finds herself quite liking some of the classic orchestral stuff! It's pretty! But Maestro cannot handle Emily singing Partition, Sweetest Pie, or Juno. Not because he dislikes it. It's just provocative and leaves him embarrassed as all hell.

Zeezi has absolutely third-wheeled and ruined some of their dates LMAO (Emily doesn't mind but Maestro hates it)

Since he took the form of some sort of fiery elk upon death, sometimes, Maestro likes being pet… but only Emily is allowed to do it since she loves cute animals, and he won't admit it to anyone else. (yes, the flames are pettable)

Remember when I said Maestro can be petty and jealous? Well any time an unwanted sinner approaches and tries to hit on Emily, he does this type of shit:

In the pilot, Maestro had an exposed portion of his brain and I think it's still there but covered up by his current phantom-inspired mask. He's extremely self-conscious about it. So to make him feel better, Emily shows him her extra eyes.

Actually, he didn't care much for Charlie's idea at all when he first saw it on some TVs at the appliance store, but he's willing to support it for Emily's sake now and defends her if someone is still mocking the concept.

Although he's shy about intimacy, Maestro is very much a romantic and will go out of his way to do things like dancing or taking Emily on elegant dates if he can.

Emily doesn't want him to go overboard and has to remind Maestro that someone like her doesn't need that, quality time in the moment is more than enough for her! 💜