Encouragement - StarShadow Series Pt. 1

So... With all of Bonnama's shipping, Arcadi (the art muse in my head) decided to throw her own hat into the shipping ring with another ship from my writing with Epic-Prose. Featuring Witching Hour and Calm Wind's eldest, Moonshadow, she turns to none other than the Princess of Love for advice...

"Go for it, Moony. Follow your heart!" ~Cadance
"But... he's my TEACHER!" ~Moonshadow
"Ah-ah-ah! You're thinking with your head again... Just do it, sweetie. Tell him how you feel!" ~Cadance

Next in the series (when I can stop looking at the sketch and crying because the outlining will be a nightmare) - The reaction to Moonshadow's confession... 

Base used: [Base] Time With My Favorite Princess by HoneyLovePonyArtist
Programs used: MSPaint and Gimp 2 as usual

I do not own My Little Pony, or Princess Cadance... If I did, I wouldn't be drawing this crappy stuff...  

Update:
Pt. 2
Pt. 3