Hook has some sort of mommy issues because every woman he flirts with is a mother.
He told Rumple that he has had “many a man’s wife”.- Since there was no contraception in FTL, it is very likely that once a woman became a wife, she’d become a mother soon after.
Milah- Bae’s mother.
Emma- Henry’s mother.
Snow- Emma’s mother.
Cora- Regina’s mother (Hook attempted to flirt but Cora shot him down)
Regina- Henry’s mother
The only woman Hook hasn’t flirted with is Belle. This could be because of her connection and loyalty to Rumple or because she isn’t a mother.
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Keeper of Felix