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Romances

Yrene Westfall

Yrene is Chaol's wife.

Chaol first meets Yrene in Tower of Dawn, shortly after Yrene is appointed as Chaol's healer. At first, Yrene hated Chaol, because he was Adarlanian, and Adarlan's army destroyed her home in Fenharrow. Over time, they warmed up to each other, and they both told each other about their own lives. They first had sex on Yrene's birthday, when Hasar held a desert party for her. They later got married, and Yrene became pregnant.

Aelin Galathynius

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Chaol and Celaena first interact in the salt mines of Endovier, after Dorian's arrival. At the beginning, Chaol does not trust her, and is persuaded she might attempt to escape Rifthold, and fears about the prince's life, when he is alone with the infamous assassin, however, Chaol does train Celaena for the royal tournament, and soon the two of them develop some kind of a bond—Westfall offers Sardothien an amethyst ring as a gift. During one of the banquets, which Sardothien attends incognito, Chaol tries to force her into returning back into her apartments, what does not succeed. The two of them share a dance. Westfall continues to support Adarlan's Assassin until the finals, encouraging her to fight off Cain and the demons.

Celaena and Chaol grow closer. On his birthday, Celaena arranges for a fancy private dinner for the two of them. She admits that she has not killed any of her targets; rather, she faked their deaths. Chaol exclaims that she is crazy and reveals his fear that the king will order Chaol to kill Celaena as punishment for being her friend. Celaena tells him that she plans to be out of the king's servitude before he finds out, living far away. Chaol worries that she will not return if she does this and realizes just how much he hates the idea of her moving far away and marrying someone else. He then tells her that he would go with her and that he would give up his duties to be with her. They kiss passionately; eventually they ride in the carriage back to the glass castle. Once they arrive in Celaena's chambers, they make love.

Things are going well until the rebels capture Chaol. Upon reading the note the rebels left for her, Celaena slips into "the killing calm" and hastily heads to the warehouse mentioned in the note. Meanwhile, Chaol overhears his captors discussing a "she" and, realizing that they are talking about Celaena, threatens to rip them apart if they harm her. When Celaena arrives, she kills several people without hesitation. After the fight pauses, Archer venomously accuses Chaol of knowing about the threat to Nehemia's life for more than a week and of being the person assigned to question her. Chaol admits to knowing about the anonymous threat but denies being the questioner.

When Celaena reaches the castle to find Nehemia and her two guards slaughtered in the princess's chambers, she flies into a rage and recriminates Chaol for her death. In their fight, she deeply scratches his cheek with her nails, leaving a permanent scar. Dorian intervenes before Celaena can kill him.

Chaol is heartbroken, but he has no choice but to carry Celaena to the dungeons. He displays a great deal of self-loathing and remarks that he deserves it if the wound on his cheek scars. After her release from the dungeons, Celaena remains angry with Chaol. She even embarrasses him in front of the king by implying that he doesn't know how to do his job. Chaol spots Celaena's will, signed two days prior to Nehemia's death, and discovers that she has willed every copper to her name to Chaol because she understands that returning to his father, should he lose his position, because he has no money would destroy him. Celaena tells him that she will not change the will.

Dorian, believing that Celaena is in serious trouble, entreats Chaol for help. Chaol readily agrees, and the two of them break into Celaena's chambers to find them empty. They find the tunnel and follow it. When the creature from the Wyrdgate grabs Fleetfoot, Chaol pursues it and rescues the dog, but the creature then turns on him. Celaena rushes to his rescue: She enters the portal, shifts into her Fae form, wards off the monster long enough for Chaol to retreat, and then creates a rift between them and the monster to keep it from returning before they can close the portal. As Celaena kills Archer, Chaol watches in horror, struggling to reconcile the woman he loves with this killer.

Celaena apologizes to Chaol for scarring him and tells him that she really did love him.

Fearing for her safety, Chaol agrees to return to Anielle if his father supports his plan to send Celaena to Wendlyn. Celaena does not seek Chaol out to say goodbye because there is so much she wants to ask, but she is afraid. Chaol locates her anyway. She tells him that she will always pick him; Chaol tells her that he loves her. She boards the boat and gazes at him as the boat sets sail.

Nesryn Faliq

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In Queen of Shadows they start showing interest in each other. Finally Aelin encourages them to pursue each other. In the British version of Empire of Storms there is a chapter from Chaol's point of view in which a romance between them is strongly hinted at.

Lithaen

Before knowing Celaena, Chaol had an affair with Lithaen. It is unknown how long it went on for, and Chaol speaks of it with great seriousness. The affair ended when Chaol discovered Lithaen in bed with Roland Havilliard, Dorian's cousin, and Chaol punched Roland. Dorian makes mention of the affair as "appointment to Captain of the Guard. If anything, it had improved his standing among the guards and lesser nobles. Lithaen's betrayal led the profoundly wounded captain to develop a total mistrust of others.

Friendships

Dorian Havilliard

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Chaol is Dorian Havilliard's good friend since early childhood, but Celaena's arrival has in some way severed that relationship. His love for Celaena is evident to Dorian.

Chaol and Dorian's relationship becomes more difficult as they both realize that they share somewhat romantic feelings for Celaena. However, after Celaena and Dorian sever their romantic ties, this makes way for Chaol and Celaena's relationship. Throughout their relationship, there are often bumps—most of those from Celaena—however they still remain close friends, although it is often implied that something has shifted in their relationship. His relationship with Dorian strains slightly when Dorian suspects his feelings for Celaena. Although both he and Celaena deny their feelings for some time, Chaol admits to not liking Celaena with anyone else, particularly when she danced with Prince Dorian during the Yulemas ball in.[3] This continues when Chaol and Celaena finally confess their feelings for one another, choosing to exclude Dorian, knowing that he'll likely figure it out anyway.

Chaol and Dorian's relationship remains strained, although Chaol claims that the reason behind everything he is doing is to help his prince. Eventually the two come to an understanding, but their friendship is never the same. There is a showdown with Dorian's father, the king, in which the king has not only arrested Aedion Ashryver for treason, killed Dorian's lover, Sorscha, and then commands the death of the captain resulting in Dorian exposing his magic to give Chaol time to escape the castle. Chaol's last words to Dorian are "I love you," before he flees.

Later, even when Dorian is possessed by a Valg prince, Chaol is fiercely protective of him. Aelin almost cuts of Dorian's head, to kill the demon inside him, even if it would kill Dorian. Chaol gets extremely angry at Aelin for that, and continues to protect Dorian despite the demon possessing him. Once Dorian's Valg collar is removed, Dorian returns to normal. When Chaol and Dorian are reunited Dorian informs Chaol that he has made him the king's hand.

Manon Blackbeak

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Aedion Ashryver

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Kashin

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Sartaq

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