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Gwendolyn Zahra Melanie von Musel de Rolo, or simply Gwendolyn de Rolo is the fifth and youngest child of Vex'ahlia and Percival de Rolo. Despite her parents being a human and a half-elf, she is not half-elven like her siblings: due to her father's pact with Ipkesh, a fiend of Dis, Gwendolyn was born a tiefling.[4][5][3]



Gwendolyn de Rolo - Mateusz Wilma

Fan art of Gwendolyn de Rolo, by MateuszWilma.[art 2]

Gwendolyn is a short tiefling girl with deep red skin, black hair with grey tips,[6] and four horns, two larger central ones framed by two smaller ones. She has slightly pointed ears, like the rest of her half-elven relatives.[7]

She looks very similar in coloration to the devil that caused her to be a tiefling.[8][5]


As of 836 PD Gwendolyn was described as very sweet and innocent.[9]

In 843 PD she was still sweet and well-behaved, although somewhat headstrong, spying on visitors and listening to what they said, arranging for her father to let her do what she wanted,[10] and convincing people to play by her rules and obey her as part of her games.[11] Despite this, her youth and innocence still become evident when she faces ill-intended emotions, such as Delilah Briarwood's hatred.[12]


Gwendolyn was born in or before 831 PD as the youngest of the five children of Lord Percival de Rolo III and Lady Vex'ahlia de Rolo. She was a tiefling, which was a notable trait in a family of humans and, more recently, half-elves. While there were rumors in Whitestone about how the cause of Gwendolyn's condition was the pacts that her father had made with fiends in his youth, the young girl turned out being charming, loved by everyone that met her.[9]

At some point in 836 PD Gwendolyn got into mischief, taking one of her father's latest creations and disappearing into the castle's dungeons with it. This prompted Percy and Vex to enlist the help of various adventurers and local elite warriors to find the little girl.[13]

In 843 PD, when Bells Hells arrived in Whitestone (with Keyleth's help) they were brought to speak with Lord Percival. Gwendolyn followed the adventurers stealthily, being barely noticed only by Orym; however, when they were about to enter Percy's office he noticed his daughter, allowing her to enter despite the grim subject they were about to deal with (Laudna's death and possible resurrection). During their conversation the young tiefling read a book about medicine, and later she got her father to let her take it with her, on the condition that she return it in good condition. Soon after, while Percy was still talking with Bells Hells, Gwendolyn came again and informed her father about what the adventurers had been talking about before they met him. Chetney took the chance to give the girl a miniature wooden rocking wolf as a gift (and a proof of his craftmanship). With Percy's approval, Gwendolyn accepted the present, and decided to name it "Galdric", in honor of the Moonlit Wolf.[14]

Orym and Gwen by Melissa Hahn

Fan art of Orym and Gwendolyn, by Melissa Hahn.[art 3]

Several weeks later, when Bells Hells were again in Whitestone, Gwendolyn spied on them again and was noticed by Orym. He saw she had a doll with a skeleton and offered to introduce her to the rest of the team. She agreed, cheerfully "commanding" the halfling to do so.[15] Initially Gwen seemed interested in the spooky stuff that Laudna was showing her, including Pâté de Rolo and her own exposed sternum. However, when the girl touched the bone she felt hatred, and although she didn't fully understand why, she left, scared of Laudna.[16] Laudna, along with Fearne and Imogen (who failed to stop Gwen by speaking in her mind), followed her to her room, but could not convince her to come out. She, however, described to Imogen what she had sensed in Laudna, telling her that she had never felt hate like that. Imogen tried to calm her down and distract her from that idea, assuring her that Laudna didn't hate her, after which Gwendolyn said that she wanted to take a nap. Before she went with her friends, Fearne left her Eyes of Charming as a gift for the tiefling, which she accepted through the bottom crack of the door.[17]

Chetney and Gwen by Elaine Tipping

Fan art of Gwendolyn and Chetney running away, by Elaine Tipping.[art 4]

The following day, Gwendolyn joined Fearne and Chetney breaking the valuable stained glass windows of Whitestone Castle. When her father saw what was happening, he seemed more proud than angry about it (although the young tiefling, encouraged by Chetney, ran away regardless).[18]


Percy de Rolo[]

Gwendolyn is, of all her siblings, the one who has the closest relationship with their father. Although he doesn't exactly consider her his favorite daughter, when he looks at her he can see several of his own negative qualities reflected, so he tries to encourage the young tiefling in the right direction.[19]

Character information[]


Gwendolyn was able to feel the deep hatred Delilah Briarwood had by merely touching Laudna's chest.[20] Later, when talking to Imogen, the girl explained she had never felt such a hate before.[21]

Notable items[]

Appearances and mentions[]


  • Her name comes from the combination of the Welsh terms gwen ("white/fair" or "holy/blessed") and dolen ("loop", "link of a chain", "ring" or "bow").
  • Since Ipkesh is a devil of Dis whose contract with Percy was signed in that layer and linked to its archdevil, the Iron Duke,[26] it's very probable that Gwendolyn will eventually manifest magic related to this legacy, such as the Thaumaturgy cantrip and the Disguise Self and Detect Thoughts spells.[27]
    • If Gwen's ability to feel Delilah's emotions through Laudna wasn't only because of the archmage's intense feelings, this might be a weaker version of Detect Thoughts, although it isn't confirmed.
  • She seems to be interested in medicine.[28] She also likes scary stuff,[29] and both interests have skeletons in common.
  • As part of her games, she considers that anyone shorter than her should obey her commands[30] (something unfortunate in a way, since she's the youngest and shortest of her siblings).
  • In a way, if Percival de Rolo were to be Bruce Wayne/Batman, Gwendolyn would be the equivalent of Robin (the superhero's classic sidekick) or Terry McGinnis (the man who takes the mantle in Bruce's old age).[31] Taliesin has stated that Gwen will probably grow up to be very much like her father, in good and bad ways.[32]


  1. See "A Gathering of Heroes" (3x76) at 2:45:33.
  2. Using as reference the fact that in that year she's considered a young girl, and the appearance she had in a portrait made 11 years before, assuming she was at least 1 then.
  3. 3.0 3.1 3.2 3.3 3.4 See Tal'Dorei Campaign Setting Reborn, p. 264.
  4. See "Vox Machina Go to Hell" (1x91) at 2:35:44.  Ipkesh has red skin, and his hair is black with gray tips.
  5. 5.0 5.1 See Tal'Dorei Campaign Setting Reborn, p. 163. Art of Gwendolyn depicts her with red skin and black hair with gray tips.
  6. See "A Desperate Call" (3x36) at 0:46:01.
  7. See Tal'Dorei Campaign Setting Reborn, pp. 264–265.
  8. See "Vox Machina Go to Hell" (1x91) at 2:35:44.  Ipkesh has red skin, and his hair is black with gray tips.
  9. 9.0 9.1 See Tal'Dorei Campaign Setting Reborn, p. 163.
  10. See "A Desperate Call" (3x36) from 0:45:57 through 1:00:36.
  11. See "A Gathering of Heroes" (3x76) at 2:44:30.
  12. See "A Gathering of Heroes" (3x76) at 2:56:44.
  13. See Tal'Dorei Campaign Setting Reborn, p. 80.
  14. See "A Desperate Call" (3x36) from 0:45:57 through 1:00:36.
  15. See "A Gathering of Heroes" (3x76) from 2:43:08 through 2:45:19.
  16. See "A Gathering of Heroes" (3x76) at 2:47:12.
  17. See "A Gathering of Heroes" (3x76) from 2:48:51 through 2:58:10.
  18. See "Fractures" (3x78) at 1:15:15.  See also at 1:28:53.
  19. See "4-Sided Dive: Why Are You Like This?!" (4SDx08) at 0:17:51.
  20. See "A Gathering of Heroes" (3x76) at 2:48:51.
  21. See "A Gathering of Heroes" (3x76) at 2:56:44.
  22. See "A Dark Balance" (3x38) at 1:39:43.
  23. See "A Desperate Call" (3x36) at 0:59:16.
  24. See "A Gathering of Heroes" (3x76) at 2:43:36.
  25. See "A Gathering of Heroes" (3x76) at 2:57:49.
  26. See "Deals in the Dark" (1x92) from 0:47:57 through 0:51:26.
  27. See D&D: Mordenkainen's Tome of Foes, 5th ed., p. 21.
  28. See "A Desperate Call" (3x36) at 0:56:20.
  29. See "A Gathering of Heroes" (3x76) at 2:47:54.
  30. See "A Gathering of Heroes" (3x76) at 2:45:33.
  31. See "4-Sided Dive: Why Are You Like This?!" (4SDx08) at 0:17:51.
  32. See "4-Sided Dive: Anxiety Game Gauntlet" (4SDx18) at 1:19:32.


  1. Official art of Gwendolyn de Rolo in 832 PD, by Jessica Scates (source). Used with permission.
  2. Fan art of Gwendolyn de Rolo, by MateuszWilma (source). Used with permission.
  3. Fan art of Orym and Gwendolyn, by Melissa Hahn (source). Used with permission.
  4. Fan art of Gwendolyn and Chetney running away, by Elaine Tipping (source). Used with permission.