Creepy AI: The Borg Queen
Lieutenant Commander Data (Brent Spiner) has been captured aboard the Borg cube threatening Earth and the reptilian Borg Queen (Alice Krige) immediately sets to work tricking him to give up critical information about the Enterprise's defenses. When none of that works, she tries to seduce it out of him, cooing "Are you familiar with physical forms of pleasure?" in his ear.
That's creepy enough coming from a cyborg, but it's ickier still when we learn the lovable but definitely not human Data knows the ways of love. "I am fully functional," Data says, "programmed in multiple techniques." Cue passionate tonsil tennis between a robot and a cyborg. Ew!