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Annie sure is a mystery huh...

All I know is she's Janet's faithful assistant, and will always be nearby whenever Janet's in the frame :)

An even better question: in this animation Janet mentions that Annie has plenty of experience when it comes to birthing. But i dont recall any (canon) instances of Annie being pregnant. Can you expliain it?

I can explain it by saying Annie has helped Janet through multiple pregnancies, so Annie has experienced, or seen, enough births to know how to deal with them.