|“|| Matt: I just want to be with you. Please take me with you?
Penny: Sorry, Matt. You don't belong with me, either. There's a better life for you out there. You just have to wake up and find it. Wake up. (echoing) Wake up!
This is the relationship between the humans Matt Donovan and Penny Ares. Their relationship started when Penny pulled Matt over for supposedly drunk-driving. They stayed as allies and friends after Matt explained the supernatural world to her, before Stefan Salvatore eventually got her killed, which left Matt devastated. It is revealed that Matt is hunting all vampires that step foot into Mystic Falls due to Penny's death. Matt now harbors a deep hatred for all vampires as result of Penny's death. However, after hallucinating seeing Penny as a ghost, Matt comes to terms with himself and moves on from Penny's death and starts a new, normal life away from vampires and the supernatural world.
Throughout The Vampire Diaries Series
In Things We Lost in the Fire, Penny first in the series and pulls Matt over for drunk driving. Despite him telling her that he is a fellow officer and that he is not drunk, she searches his vehicle. After the scene, she apparently arrested Matt and he was sent to jail because of this. Penny later informs Matt that he is relieved of his crime. After Matt refused to go and decided to wait for her, Penny discusses the death of Matt's class, stating she feels sorry for what had happened to him and would be devastated if the same incident happens to her. She then showed Matt a bag full of weapons, asking Matt what was what they found in his truck.
In Postcards from the Edge, Matt is still jailed in his cell while Penny studies the weapons she and her fellow officers found the night before in his vehicle. Matt lied to her and claimed that the weapons they found originally came from zombie apocalypse survivalist, which she believed. She releases Matt and told him to cheer up because a friend of hers, named Doug, got a call from the Mystic Falls city planning office to reclaim his house. Penny believes that this is a sign of support for Mystic Falls, however, Matt asked curiously which street Doug lives in. It is revealed that Penny did not believe anything Matt said as she followed the latter into a house in Mystic Falls. She asks Matt what he is doing as a vampire appears before them. Matt shoots the vampire and told Penny that if she's coming to Mystic Falls, she better bring some wooden bullets with her. In the woods, Matt and Penny are sitting on his truck, drinking. Shocked by the existence of vampires, Penny asks Matt if there are more things he should tell her. Matt tells her that one is enough. Penny then claims he is different from what she thought he would be, describing him as "cute, a little damaged in a sweet way, and insanely brave", which pleases Matt.
In I Would for You, Penny and Matt are amusing themselves with a scenario they have been playing along with on how to trap Julian's vampires for a couple of days. They are surprised by vampires from Julian's army however, Krystal and four more of them. Shortly after, Julian's vampires fall to the ground, stabbed by Rayna Cruz, who asks Matt if he knows a vampire named Stefan Salvatore. Later, Matt and Penny on Rayna's side, she interrogates a vampire at the Grill. Rayna wants to know where Stefan is. Matt covers for Stefan and teams up with Damon when he barges in. Matt shoots Rayna in front of Penny. Then, alone at the Grill, she asked him why he chose to help Damon. Skeptical about the fact that they're are some good vampires, she points out that all Matt has been talking about lately was his hate for that species. She questions his motives and she accuses him of being guilty as the vampires in what the town has become because he never took a real stand, he is hurt by this and begins to question his standpoints.
In Days of Future Past, Matt is seen standing over Penny's tombstone. It is later revealed that Stefan Salvatore had something to do with Penny's death. This explains why Matt set Rayna Cruz free from the imprisonment of the Armory and to let her chase down Stefan. Penny's death is what influenced Matt to hunt and hate all vampires, especially Stefan.
In Kill 'Em All, a flashback is shown of them deciding to get married while Stefan expresses his condolences to Matt about Penny's death, after they talk about Matt's almost-wedding.
In Gods and Monsters, Matt is still stuck in his truck and he dreams of seeing Penny's ghost. They share a heartfelt goodbye as Penny convinces him to move on and not blame himself for shooting her. Penny also tells him to move on from Mystic Falls.
- They were originally in a negative relationship being Penny arrested him when they first met.
- They later become friendly when they get to know each other.
- Penny admitted to him that she thought he was cute, implying that she has a crush on him.
- In a flashforward, it is implied that Matt loses someone in three years, this possibly references to Penny and that they are in a future, romantic relationship together.
- Matt eventually was the first person to tell her about the supernatural world and its existence in Mystic Falls.
- Penny blamed him for the problems with the supernatural world that were ruining Mystic Falls.
- Matt hates and is hunting all vampires down, especially Stefan Salvatore, as a result of Penny's death.
- Stefan Salvatore is indirectly responsible for Penny's death. It was Matt who really killed her, but Stefan compelled Matt to forget this.
- They were engaged to each other in Kill 'Em All shortly before Penny was killed.
- Penny's death is the reason Matt hates all vampires.
- Matt still blames Stefan for her death despite Matt being the one to pull the trigger and fatally shoot Penny.