I have a headcanon that Elaine took in Calico Jack a long time ago when he was still a baby, and he views her more like a mother figure who is rude and dangerous in public, but quite kind to him.
so, here a little hc on Calico Jack's coming out as a transgender when he was a teen :
CJ: E-Elaine... I have something I'd like to tell you.
E: What-? What is this huh?
CJ: I think that... that I'm not a girl. not at all. I... never felt like who I am.
E: so... you wanna say that you-
CJ: yes.. I think I'm a transgender.
CJ: are you... mad at me?
E: ...no. not at all, I would never.... so, listen here. I want you to know that you're very strong as being trans. I have never felt this. like, gender euphoria and other stuff.. but. you're valid for me. you're a strong boy.
CJ: ...o-oh... I thought that you would-
E: I'm not homophobic. I'm a lesbian, how the hell I can be homophobic-?! erm, nevermind. so, how can I.. call you for NOW???