Thoughtful was a male, NightWing dragonet who appears in Darkstalker (Legends). He wears wires around his horns that hang circles of glass in front of each of his eyes (spectacles), and is described by Clearsight as being handsome, but having a kind and worried aura. He is first seen stacking scrolls at the game pavilion during Queen Vigilance's Glass Jubilee. Listener had a crush on him, but Clearsight saw that he was destined to be with Whiteout, Darkstalker's sister. He was said to have a similar way of thinking to Whiteout, which leads her to the conclusion.
While Darkstalker, Fathom, and Whiteout were playing scales-and squares, Thoughtful asks if anyone would like to do a scroll stacking challenge with him. Listener, who was nearby, started to go with him, but Clearsight, who sees that he is destined to be with Whiteout, introduces him to her. After a short talk about Thoughtful's glasswork, Cascade of Dreams (in which only Thoughtful and Whiteout seemed to actually understand), the two walk away to play their game. After Quickdeath failed to assassinate Darkstalker and was killed, Thoughtful was the one who identified the body. He guarded the body with Whiteout while Darkstalker and his friends set off to find who hired Quickdeath. Later on, Darkstalker asks Whiteout about her new admirer and she says she likes Thoughtful. He was one of the reasons Prince Arctic decided to take Whiteout to the Ice Kingdom since Arctic apparently didn't like him. Thoughtful also appeared after Arctic's gruesome death, pushing through the crowd to comfort Whiteout.
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- Since Darkstalker did not have any dragonets, all NightWing animus dragons are descended from Whiteout and Thoughtful. This means that he is an ancestor of Stonemover and Sunny.
- The circles of glass in front of Thoughtful's eyes most likely act as glasses, which shows him as the first near-sighted dragon mentioned in the series that isn't blind and has something to help him see.
- This also proves that NightWings were very scientific before fleeing from the Old NightWing Kingdom.
- Unlike most dragons, Thoughtful seems to know what Whiteout is talking about.
- This could mean that Thoughtful has a very powerful mind reading power, as he is able to talk to Whiteout very successfully, while as Darkstalker, Whiteout's brother, could only see her thoughts in color.