Ref
Has had a massive crush on her from almost the moment he met her.
First meeting:
They first met when the pirate* ship Shadow was on got shipwrecked outside of the town Frey lives in.
Shadow got wounded and was taken in to the healing center (pretty much a fantasy version of a hospital) and got tended to by Frey.
He didn't want to stay there ("I can take care of myself, I don't need a doctor"), but Frey pretty much commanded him to stay until he's in good enough shape ("Either you stay here willingly, or I will MAKE you stay :)"), and so he did.
Shadow started crushing on her very quickly after being commanded to stay, although he didn't realize it at first.
Frey eventually started crushing on him a bit later on, but before he got out of the healing center.
*By pirates I mean the 'Sailing around the world, looking for buried treasure and maybe occasionally doing some illegal things' kind rather than the 'pillage and plunder' kind.
Shadow's thoughts on Frey
"She's... very kind, yet won't take shit from anyone...and so skilled and strong and independent... ///"
Frey's thoughts on Shadow
"He may seem all distant and cool, but he's really a big sweetheart! ♡"
Frey is generally the one with more energy left after they're done and often carries Shadow to the bath while showering him with praise and compliments.
Shadow is usually pretty ready to pass out after they're done, but sometimes has more energy left. He always tries to make sure Frey is doing okay before he passes out though. He also does compliments, although he's more shy about it.
They always end up having a nap afterwards unless it was something very quick and then getting something to eat and drink (sometimes even before they take a nap)