A sphinx arrives to Mystic Falls and is captured by Hope, Lizzie, and Josie. The sphinx seems to have no intention of taking Landon to Malivore and reveals that he can see the future, but he will only reveal what he sees in the form of riddles. Josie realizes the projection crystal can be used to create a temporary physical manifestation of Landon's subconsciousness to trick Malivore. Simulandon keeps professing his love for Hope, but the real Landon is more reserved, pointing out that he's much more complex than his subconsciousness, and still hasn't decided if he wants to be with Hope or Josie. Landon sets up a blood transfusion from Hope to Simulandon in order to destroy Malivore using the Trojan horse. Meanwhile, Dorian and Alaric figure out that Headmaster Vardemus is actually Ryan Clarke. They evacuate the school. "Vardemus" tricks Josie into charging his trident dagger with dark magic. He then appears in Hope's room, shedding his disguise, and explains that his physical body is decaying due to a fail-safe added by Malivore to ensure Clarke's obedience. His plan is to use the dagger to transfer his mind into Hope's body, becoming a powerful tribrid. Hope, weakened from the blood loss, manages to evade him and runs outside, where she is rescued by Simulandon, who tricks Clarke into using the dagger on him instead. Clarke possesses Simulandon's body and realizes he only has a few hours to live before the physical illusion dissipates. His own lifeless body is dragged away by the zombie. Landon decides to leave Mystic Falls in order to protect the people he cares about from Malivore's monsters. Rafael goes with him. Josie and Hope make up, as Hope decides to return to the Salvatore School. Alaric and Dorian confront the sphinx, who explains that he orchestrated Landon leaving in order to keep him out of Malivore's grasp. He states that something worse than Malivore is coming, before delivering another riddle and then slashing his own throat.
- Body Horror: To demonstrate his decaying body, Clarke scratches as the side of his face, revealing his muddy golem nature.
- Body Snatcher: With his own body decaying, Clarke plans to use the trident dagger to take over Hope's body. Simulandon tricks him into using the dagger on him, though, as Clarke doesn't know that the Landon he's fighting isn't real. This proves to be his undoing, as Simulandon will disappear in a few hours.
- Cat Folk: The sphinx looks like a typical cat person, albeit one wearing Egyptian-style clothes. At the end of the episode, he calmly slashes his own throat with a claw, quickly crumbling into a pile of sand, although his words imply he might come back in the future.
- Five-Finger Discount: Apparently, Hope is very good at pickpocketing. She manages to steak Clarke's illusion ring off his finger without him noticing.
- Glowing Eyes: The sphinx's eyes glow whenever he sees the future.
- Internal Reveal: Everyone learns that "Headmaster Vardemus" is actually Ryan Clarke in disguise.
- Literal Split Personality: Sort of. With some help from "Vardemus", Josie uses the projection crystal to create a physical manifestation of Landon's subconsciousness. The Simulandon has no filter and just spouts whatever he thinks, so he's constantly professing his love for Hope. The real Landon is more reserved and is still bitter about Hope's duplicity.
- Riddling Sphinx: Sphinxes love riddles. Some of them the characters are able to solve quickly, including the most famous one: "what walks on four legs in the morning..." The sphinx captured by the witches only reveals the future in the form of riddles.
- Seers: The sphinx reveals that his people can see the future.
- Shout-Out: Lizzie refers to Headmaster Vardemus as "Headmaster Downton Abbey" due to his accent and manners.
- Take a Third Option: In the choice between Josie and Hope, Landon chooses neither, opting to leave town instead. Both girls accept his choice and make up.
- Title Drop: Spoken by the sphinx shortly before he slashes his own throat.
- Vagueness Is Coming: The sphinx is pretty vague on the threat he claims is looming on the horizon, obscuring his words even more by being a stereotypical Riddling Sphinx.
