I wanna ship him with Discord but I doubt he could handle that dude with all the emotional baggage he has now.

@Danilo  
The final fight was much worse.

@Jades  
I doubt she stayed in the shadow world 24/7, 365 days a year for the entire time she was learning about the Umbrum. She would still have to be aware of current events, like Chrysalis getting loose again for example.

@Jades  
Possibly not.
 
I doubt the umbrum are that good at acting.

@soundtea
 
Speaking of which would Hope even know how to act?

@Vree
 
Reminds me of the Ask King Sombra blog.

“My my, aren’t you a cute couple!” the old lady at the counter said in a conversational tone. “Are you on your honeymoon here?”  
“Ah, er, actually, we’re on a, er…”  
“A tour” Hope helped out.  
“Ahh yeah, right.”  
“Make sure you visit the Crystal City. It’s beautiful there at this time of the year.”  
“I, er, think we might be skipping that…”  
“What HE’s saying” she interrupted “is that we thank you for your recommendation and we will certainly take it into consideration. In the meantime, can we get our tickets to Manehatten?”  
(Hope, stop talking for me. I can do this.) he whispered as the old lady shuffled behind the shelves.  
(We can’t risk anyone recognizing you, Sombra, you know we can’t go back to…)  
They stopped when they saw the old lady re-emerge and eye them suspiciously.  
“What did you say your name was again, young stallion?”  
“Er, my name is…Som…um…Sombrero! That’s right! Because we are…uh, Mexican dancers!”  
He glanced sideways at Hope to see if this was okay, who was covering her eyes.  
“Oh, how delightful! Are you going to perform here today? I’ll call all the little colts and fillies around to watch!”  
“Um…”
 
The legend of “Sombrero” is only just beginning…

@soundtea  
“Welcome to Fetlockshire, strangers!”  
“Hey, you guys got any crystal ponies you need me to enslave?”  
“SOMBRA!”  
“What? It’s the one thing I’m good at!”

@Background Pony #5A48  
Legends say they are still roaming the countryside today

What a shity ending

Hours later when they’re approaching the nearest town
 
Hope: “… Oh crap, Sombra has no damn clue how to act in these days outside.”

Now there’s an adorable couple!