I think Hook has some mommy issues hence why he tends to go for women who are mothers.
He told Rumple in the Crocodile that he has had “many a man’s wife”. Most women when married would have likely become mothers soon after as that would be seen as doing their duty.
He stole Milah off of Rumple- she was Bae’s mother.
He’s flirted briefly with Snow- she’s Emma’s mother.
He’s flirted a lot with Emma- she’s Henry’s mother.
He tried to flirt with Cora until she shot him down- she’s Regina’s mother.
It seems the only woman he’s not flirted with is Belle. There are two reasons why this could be, first- her association with Rumple, and second- she’s not a mother.
The only mother Hook hasn’t flirted with so far is Regina.
All magic comes with a price!
Keeper of Felix