ménage à troisNow that you mention a regrown tail fin...although I was thinking dragon limbs were like human's and they can't grow back...maybe Toothless comes back once a year, or every 5 years or something, to get his tail fin fixed, so they still get to see each other...?


I'm thinking if there is a reunion maybe it could go something like this: (If other's have posted this, I'm sorry! I've seen/heard some theory's and they kinda blend together after a while.)
Hiccup says "There were dragons when I was a boy." right after the main story line for HTTYD3 ends and it fades into the beard scene with Hiccup telling his kid/kids the story. One of the kids, or Hiccup spots some figures flying in the distance. As the figures get closer they can tell the figures are dragons. Hiccup grabs the Dragon Blade, just in case. Then Toothless runs into Hiccup and starts licking his face. Hiccup immediately realizes it's Toothless and he's ecstatic to see him. They meet the Nightlights and then after a while Toothless and his family go back into the Hidden World.

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