*le drumroll*

I Headcanon Caleb as a Trans man.

Inspired by this headcanon:
https://www.tumblr.com/blue-jacket-blues/729301403152089088?source=share

Extra notes I'd like to add: If Caleb's mom lived to see her son, I'd imagine she'd be very supportive of him. So what? The doctors were wrong for telling her she had a girl, because that's her SON, not her DAUGHTER.

Caleb, once free of the Fog and and once the whole glitch thing is over, he would definitely tell Alastor. I'd like to believe Alastor doesn't really give a sh*t about it, in a positive way. Thats still his friend, trans man or cis man.

Caleb's always worn his hair long, because he just like how that looks on him. Plus, I'd like to imagine he grew up along with a few native american people in his town or somewhere near, so he most likely saw the men wear their hair long and this decided to keep his hair long.

Caleb would 100% get top surgery (AKA Teetus Deletus), and you can't convince me otherwise. So what if it causes him pain? His leg already causes him enough trouble as is, this will be nothing. Besides, Alastor, Cobalt, Louise, and the other killers are gonna help him after.

I also imagine that he is Demisexual Demiromantic because in the quotes for his valentine's  day skins, it always stated that he never participated, and how cupid always tended to pass him by.

One of the things Caleb is greatful for in the modern day is finally having words to express what exactly he is, (Trans, Ace Aro), because back then it was just a complex jumbley mess. Now it's plain and simple, just how he likes it.