By hacking into Undertale's files, you can find a secret room named Room 123 in Waterfall. By moving through the grass, you can encounter a monster trying to catch a bug. If you continue to talk to her, she'll ask you to "do something about your friend."
After examining this dialogue, I've come to the conclusion that this could match 4 different people. But who are they?
Sans is frequently implied to be following you throughout the game, and he is constantly smiling. However, when I think of this:
I don't think of it as creepy, I think of it as jolly. His smile is supposed to put you off-edge, which makes it even more surprising when he fights you at the end of a Genocide Route. You might be thinking, "What if he's doing his bad-time face?" That might be a possibility, but I doubt he makes that face all the time, especially if you're doing Pacifist at the time.
So we can officially rule out Sans as a suspect.
Flowey's smile can definitely be described as creepy. However, like Sans, he doesn't do his "evil face" all the time, especially not while he's following you. And, like Sans, this face:
It's not supposed to scare you, it's supposed to trick you into thinking Flowey was friendly. So unless the bug-catching monster was all-seeing, I doubt she would have noticed Flowey was evil. So we can eliminate Flowey as a suspect.
It is almost confirmed that Chara would be following you around the Underground. And Chara's face can DEFINITELY be described as creepy (this doesn't necessarily mean they're evil). As for the fact that the monster can see Chara, this room is only accessible through file-editing. So it would make sense that this monster cannot really be considered as an Undertale Canon character. So I think we can put Chara as Suspect #1.
This one requires a bit of inferring. If we assume that this unknown monster is Gaster:
Then his smile could defintely be seen as creepy. Considering the fact that this room can only be accessible through file editing, and Gaster is seen in almost every file-edited room, it would make sense for him to be the "one with the creepy smile".
Who do you think it is, Chara or Gaster? Or maybe Sans or Flowey? Maybe we'll never know...