"Tootsie Pop Licking Challenge!" is the 40th installment of Ian is Bored.
This video shows Ian trying to finish a tootsie pop in the most ways he can. It eventually becomes more painful as Ian overexaggerates and is shown with his tongue bleeding and eventually dying.
Ian quickly rubs the tootsie pop on his tongue and removes it with his mouth still wide open afterwards. The title card appears.
Ian welcomes viewers to another episode of Ian is Bored and says he will be seeing how many licks it takes to get to the center of a tootsie roll pop.
The camera shifts to another angle and he begins counting aloud. Ian first licks the candy by bringing it to the center of his tongue, sliding it to the tip and removing the pop from his mouth. Other times, he brings it just past the tip of his tongue and slides it to the end of his tongue and out once more. After 105 licks, he shows the tootsie pop to the audience.