One of the deep tragedies of the Star Wars universe is that Leia and Obi-Wan never met or interacted. I lament this partially because Obi-Wan was one of the only people who could have an modicum of sense for how it felt like to be Leia post-Alderaan’s destruction – who else would know what it felt like to know almost everyone you ever knew or loved was dead and lie awake at night wondering if you could have done anything different…and knowing you couldn’t have???
But also because they are the lords of snakiness and the banter would have been gold.