Relationship between Jester and Mollymauk

History
Mollymauk Tealeaf and Jester Lavorre first met in Trostenwald when Molly read Jester's fortune with his custom-made tarot decks for 2 copper pieces. He gained a great deal of insight on her, noting her excitability. The first card was a Silver Dragon, which denotes a person of purity and virtue, the second card was an anvil, which is a "destiny forged", and something "bright and adventurous in their future." The last card was the Serpent card, which amazed Jester. Jester also told him that she was looking for her dad, and Molly pulled the Eye card, telling her she already found a clue.

Their relationship progressed over their time in the Mighty Nein, and they grew closer in Zadash. Jester and Molly got along well during his time with the Mighty Nein. When dramatizing her Hellish Rebuke in Infernal, Jester chose phrases to make Molly laugh; without Molly there, she generally just screams. Jester grabbed his horns at one point, and he said he was fine with it.

When the Mighty Nein tried to find where Jester, Fjord and Yasha Nydoorin went after they were kidnapped, Molly shouted "The Traveler's bullshit!", and remarked that if she didn't respond something was wrong.

After the group reconvened, Jester was the first to ask what happened to Molly. She assumed he simply wasn't around first, as though she couldn't believe he was dead. She and Fjord heard the fight outside, and she carried the guilt of not being able to save him.

When Beau questioned the validity of tarot card readers, Jester defended them citing Molly, remarking that he was "super smart" and "basically a god", to the chagrin of Beau. Beau gave Jester Molly's tarot deck, and Jester declared that she was going to learn how to read them.

In "Bathhouses and Bastions" (2x90), Jester found research that led her to believe that Moonweaver-specific tarot decks were meant to be "deceptive" and "relative" to those who the deck was being read to, as are the The Moonweaver. This research allowed her to realize that Molly's tarot deck was not only self-created and incomplete but also did not correspond to more traditional tarot decks found within Exandria. Several of the cards appear to be based on members of the Mighty Nein. Jester decided to finish the deck with some of her sketches as well.

When the group found Lucien, Jester maintained hope that Molly was still in the body. She gave a fortune reading to Lucien using Molly's deck, which had been slightly modified with her own addition. She pulled the Death card, and remarked that "something must end for something new to begin".

During the Neo-Somnovem battle with Lucien, Jester said she never forgave herself for Mollymauk's death. During the resurrection ritual for Mollymauk, Jester gave Molly's tarot deck as her offering and said "So I took the cards and I've added a few to it. And I think you're going to be super impressed with everything I've been doing. But I still need you here to teach me everything because I'm kind of bullshitting, Molly. I don't really know what I'm doing, so if you could, like, come back and be my sensei, I'd really appreciate that." When the ritual initially failed, she was heartbroken, but through Caduceus Clay's Divine Intervention, the tiefling was resurrected.

Initially after his resurrection, Molly seemed confused and child-like, repeating the word "Empty" over and over again, but seemed to recognize the Mighty Nein, and referred to them as the tarot cards he had made for them, Jester's being "Joy". Jester was quick to paint a replica of Molly's original clothing using Nolzur's Marvelous Pigments, save for his coat as Yasha gave him back his original. Once the Nein are safe in the Blooming Grove, Jester attempts to talk with Molly and show him his cards, but finds that he is still vacant and unable to speak. The next morning Jester casts Greater Restoration on Mollymauk and he is able to speak, but his memories still gone, other than vague images of a dream of a circus, a beautiful woman in a red coat who showed him secrets, an angel, and adventures where he felt kingly. Jester asks what he wants to be called and he decides on "Kingsley Tealeaf". He finds Molly's old clothes a bit garish and Jester paints him a sleeveless black coat. Thinking that Kingsley needs something to defend himself with, Jester gives him the Inescapable Lash.

Kingsley asks to enlist in the crew of the Nein Heroez, joining Fjord and Jester on their future pirating adventures, until he eventually gets his own ship, naming it the Mollymauk.