Relationship between Jester and Caleb

Relationship
Jester and Caleb are very close friends. Their relationship has evolved significantly since the beginning of the campaign. It had a rocky start, as Jester came from a sheltered, lavish upbringing and Caleb has a very troubled past and came from a poor household, which means their world views are very different. Initially, their interactions mostly involved teasing from Jester. However, it has since evolved. Caleb fell in love with Jester, which has heavily influenced his goals and view of the world, and Jester has in turn come to rely on him to provide emotional understanding and support.

Caleb has been "a little in love" with Jester since their waltz in, although he regards his feelings as "useless" and "a problem" and feels that either Beau or Fjord would be better for her.. Caleb appreciates Jester's positive attitude and playfulness that remind him of the life he could have had, if things had gone differently for him, and during the time before he revealed his past to her enjoyed the fact that she saw him as he could or should have been. Although he hides his feelings, Caleb often goes out of his ways with gestures to please or help Jester, and she always thanks him sweetly. Jester, on her side, has never brought up romantic feelings towards Caleb, but cares a lot about him. She often asks him questions, teases him, and tries to cheer him up. She has several times admitted to him her doubts and fears that she hides from the rest of the party.

Caleb was attracted to how Jester treated him like the good person he should have been if his traumas hadn't happened to him. Caleb knew that, despite his feelings, he would not be the best person for her to have a relationship with, because he had ambitions that would always mean he put her second.

History
Jester was friendly but blunt toward Caleb when they first met. The first thing she ever said to him was that he smelled really bad and that he should take a bath. Although he seemed not to be bothered at the time, Caleb later admitted her jokes about him being dirty had previously made him uncomfortable. Now that he has gotten to know Jester, he is fine with it.

Caleb stated on many occasions that Jester is likable and charming. He showed her his spellbook in the same way he showed it to Nott. Caleb likes that Jester cheers him up. He thinks she is an "amazing woman" but suspects that her cheerful personality is sometimes an act.

When Jester returned from the Pillow Trove and revealed that she had not gotten the expected care package from her mother, Caleb offered her 50 gold of his money to cheer her up. She declined, saying that that was nothing, and the two began to quarrel over what constituted "a lot of money". Caleb claimed 50 gold was more money than his family had ever made, to which Jester responded that basically had been her daily allowance growing up; frustrated with her inability to be happy with the money they did have, Caleb smeared mud over his face and then stormed off, though Jester later apologized for her unintentional insensitivity.

During the festivities in Hupperdook, Jester asked Caleb to dance and, very drunk after the drinking contest, he accepted. During their waltz, he told her, "You were always a better dancer than me, Astrid. You were always so good." When she reacted in surprise, he realized it was not Astrid but Jester in his arms, and broke away to start stumbling off. Jester stopped him, took him upstairs, and tucked him into bed, saying, "I'm sure Astrid loves you very much."

In a conversation in Darktow, he asked Jester if she was sweet on Fjord, and when she said she didn't know, said that her confusion was a little outside his realm of experience. When she asked about Astrid, he confirmed that Astrid had been his girlfriend.

After Caleb was attacked by the captive scourger and watched her be executed in front of him, Jester walked up and took his hands, telling him that she knew that it was very hard and didn't go the way he was hoping. She told him if he needed anyone to talk to about it or anything, she was here for him.

After a conversation with Essek during which Jester felt she fumbled her explanation of the Traveler, Caleb noticed that Jester was worried. He told her that the Traveler was lucky to have her, and that although he was the transmutation wizard, she was the one who changed people. She confessed to him that the Traveler didn't reply when she called to him earlier and she wondered if that meant she's a bad cleric. Caleb reassured her and showed her the amber-colored unicorns he could now produce with Major Image, suggesting their use for Traveler Con. Jester was amazed, and she hugged him.

In the middle of the night, as the Nein camped on their way to visit Isharnai, neither Caleb nor Yasha could sleep. During their whispered conversation, she asked him, "Do you love her?", not specifying who she was talking about. Caleb appeared to panic, and told her, "It's too late." Liam later confirmed on Talks Machina that Caleb panicked because he thought nobody could tell he was in love with Jester, and that Caleb regarded his feelings as "useless" and "a problem", thinking that either Beau or Fjord would be better for her.

Before and during Traveler Con, Caleb helped Jester organize the event. On each day, Caleb used Programmed Illusion to create a Traveler-themed image in a different location that would last indefinitely, thrilling Jester (and the village children), as well as arrows pointing up the volcano path. During the event's opening ceremony, Caleb cast illusions around the stage to enhance the experience, as well as Major Image to give Jester giant butterfly wings flapping gently. Caleb then noticed a nondescript man standing next to him casting a spell to create a vine throne for Jester, and recognized him as the Traveler, who seemed a bit jealous.

While in Rexxentrum, Caleb led the Mighty Nein to a tavern, and nudged Jester towards Fjord as he led Beau to the dance floor. However, immediately after Jester kissed Fjord's cheek when he gave her a tiny porcelain unicorn, Caleb danced Beau over and swapped partners, dancing away with Fjord.

Caleb worried most about how Jester would react to his past if she learned of it. When in Felderwin he shared with the party his real name and a bit of his past, he omitted that he had killed his parents and spent eleven years in an insane asylum. Instead of reacting in horror, she told him she believed he was a good person. It was not until much later, after receiving Trent Ikithon's invitation to dinner while in Rexxentrum, that he finally shared that he had killed his parents. Jester hugged him and told him she was sorry he felt like he had to hide that.

When Caleb created his tower, he put a lot of care into each member's living quarters. He completely recreated Jester's bedroom from Nicodranas, although he updated it a bit to make it more elegant. On the underside of the bed's canopy is the same painting that she did of Nicodranas, the lighthouse and the sea, but the painting is undulating ever so imperceptibly, and one can hear quiet sounds of the city and the ocean after staring at it for a moment. On her bedside table, similarly to all the other bedrooms, Jester found five books, including a children's book entitled Der Katzenprinz. Because the book was written in Zemnian, she brought it to Caleb, and he read it to her.. After Caleb learned of the budding romantic relationship between Jester and Fjord, he seemed to pull back from interactions with her. However, when half the party spent the night in the Elemental Plane of Fire, he asked for her help to put the power source into his antimagic necklace, which he had tried and failed to do several times. She was successful, and she urged him not to blame himself for the party being pursued by Trent and all that had followed from that.

Trivia

 * Jester's and Caleb's playlists have featured a song about the other character.
 * In Jester's first playlist, Laura wrote "A song for Caleb. Jester wants to help him step away from the flames. She just doesn’t know how to." as commentary for the song Put the Fire Out by The Colourist.
 * Caleb's second playlist originally featured the song She by Dodie. Liam chose the song because he thought the lyrics about not feeling allowed to love a girl resonated with Caleb. The song was later removed from the playlist to avoid hurting fans by associating the song, which is about a woman's feelings for another woman, with a man's feelings for a woman.