Dialogue between them indicates they have a long history together; having apparently been childhood sweethearts, Crawford once asked Pearl to marry him and was deeply disappointed when she refused his proposal, as well as being clearly grief-stricken after she is assassinated by Jacob Frye as one of his minions.
In that one, Kara tries to find Supes a girlfriend.
When I entered the room I saw her holding my son to her breast, letting him suckle.
Ronald, as the next male-line heir, ought to be inheriting everything that Clare's father left to her.