|“|| Matt: Well, you did just save my father and pretty much the entire town, so... that counts for something in my book.
Damon: Does that mean we're good?
Matt: Not by a long shot. But you keep earning it the way you did tonight, I'm not ruling anything out.
The relationship between the cured vampire Damon Salvatore and the human Matt Donovan started in Season One. Matt hated Damon at first because Damon turned his sister into a vampire. However, over the years have developed a tentative alliance as fellow members of the Mystic Falls Gang, albeit an antagonistic one. Damon always jokingly blames Matt for everything bad that happens, and Matt often seriously blames everything bad that happens on Damon.
They are referred to by the fans as "Datt" or "Mamon".
Throughout The Vampire Diaries Series
At first Matt really disliked Damon because of Damon's evil and selfish ways, and also for him turning his sister, Vicki Donovan into a vampire.
At some point when Matt arrived back at the boarding house, he saw Damon and his mom Kelly Donovan making out. He was really upset with his mother for this, telling her that she was the adult and should act like one.
In Growing Pains, Damon blamed him for Elena for turning into a Vampire. He even attacked him at the end of the episode, but Elena (now a fully in-transition vampire) pushed Damon away and sharply told him to stop hurting Matt.
In Kill 'Em All, Damon and Matt don't interact in this episode. However, Damon mentions to Stefan on a phone call that he doesn't believe Matt to be capable of releasing Rayna Cruz to hunt Stefan.
In Requiem for a Dream, Matt tricks Bonnie Bennett by allying with her to hunt down and kill Damon in Mystic Falls' woods. However, just before Bonnie kills Damon, Matt shoots vervain darts in Bonnie's back, which knocks her out. Damon thanks Matt for saving his life. They then ally to help Bonnie get through her Huntress phase.
In An Eternity of Misery, Damon originally meets Matt's father, Peter Maxwell, in order to recover something Sybil, (the Armory's creature) needs. However, Matt comes in and shoots Damon in the head in order to save his father. Later, Matt ties Damon up in chains and interrogated him. Damon reveals that he didn't know Peter was his father and he also revealed that he killed Tyler Lockwood, which Matt states he'll never forgive him for.
In Coming Home Was a Mistake, Damon crashes Tyler's first funeral and attempts to kill all his friends. However, Matt tries to stop him by shooting him in the back. This backfires when Damon puts Matt in a chokehold and force-feeds him vampire blood. Matt is disoriented in Damon's strong hold as the rest of their friends beg Damon not to kill Matt and have him turn into a vampire. After much convincing, Stefan was able to get Damon to let Matt go and Damon then vampspeeds out of there.
In Detoured On Some Random Backwoods Path to Hell, Matt is seen with Alaric helping out at the Armory. However, Matt puts the idea of fighting back in Alaric's mind. Matt later accompanies Alaric in the hunt to subdue and kill Damon due to the mess he made in everyone's lives. Matt had no problem helping Alaric kill Damon.
- Matt: "Hey, is Elena here?"
- (Damon turns around and rushes towards Matt. He grabs him by the throat and pins him up against a wall, choking him.)
- Damon: "In what world are you the one that gets to live?!"
- Matt: "Go ahead and kill me. You can't possibly hate me more than I hate myself."
- Damon: "Oh, yes I can."
- (Damon places his foot on Matt's throat and begins to push down.)
- Damon: "It should have been you."
- -- Growing Pains
- Alaric: "Yeah, and, uh, how long until that happens, huh?"
- Damon: "Pretty soon thanks to Donovan... A phrase no one has uttered ever."
- -- Age of Innocence
- Rayna: "Seems foolish of you to come back here."
- Damon (about Matt): "I know, right? To be honest... I'm not that brave. However, I did have a shockingly effective ally tell me that you were here."
- Penny (to Matt): "What the hell did you do?"
- Matt: "It's okay, Damon's a..."
- Damon: "Aw, you almost said "friend." How sweet."
- Matt: "His brother is a friend. And that's the only reason I'm helping him."
- Damon: "And the world yawned. Get rid of this thing."
- Matt: "Anything else?"
- Damon: "Yeah. You know where I can get a buzz saw?"
- -- I Would for You
- Damon: "I gotta hand it to you, Sheriff. You're a better shot than Liz Forbes ever was. May she rest in peace."
- Matt: "Those shots bought us eight hours to get Bonnie as far away from the rest of you as I can. I don't want to waste a second of it talking to you."
- Damon: "Hey. That was my way of saying thanks. Now that you're in charge, maybe you and I should start getting along. I've actually got a pretty good track record with the sheriffs in this town."
- Matt: "I did it for her, not for you. Even if you absolved her of killing you, she'd never forgive herself. I'd never forgive myself."
- Damon: "Look, man, what happened with Penny..."
- Matt: "Is my fault. And I'll be paying for it the rest of my life, starting with taking responsibility for Bonnie. So if you want to thank me, figure out a way to fix her."
- -- Requiem for a Dream
- Damon: "How are you feeling, sport?"
- Matt: "Like I just had my head rammed into a giant metal object."
- Damon: "Hashtag you're welcome. Your dad was looking pretty rough, too. I put the hell bell in the back of his truck and sent him on his way. You're not gonna do anything stupid like chase after him, are you?"
- Matt: "Well, since Stefan compelled me to ring the bell by 9:00, I'd say we're in the clear. For the record, it's hard to thank you for something that's pretty much your fault."
- Damon: "Hey. Matt. I'm sorry about Vicki. I know you'll never forgive me for what I did, but... I should have told you this a long time ago."
- Matt: "Let me guess, your emotions are back on, huh?"
- Damon: "Yep. It's gonna be a bumpy ride."
- Matt: "Well, you did just save my father and pretty much the entire town, so... that counts for something in my book."
- Damon: "Does that mean we're good?"
- Matt: "Not by a long shot. But you keep earning it the way you did tonight, I'm not ruling anything out."
- Damon: "Fair enough. Need a lift?"
- Matt: "Nah. Got to stop by the police department. I hear Mystic Falls needs a sheriff."
- Damon: "Always did like the sheriffs in this town."
- -- Nostalgia's a Bitch
- Matt and Damon have been on and off enemies/allies for most of the series.
- Damon killed and turned his older sister Vicki Donovan into a vampire.
- Damon blamed him for Elena Gilbert's transition into a vampire.
- They both had siblings who have died (and came back).
- Both of them have died at least three times.
- Damon killed him once.
- Both Damon and Matt have had romantic history with two doppelgängers from the Petrova family.
- Both Damon and Matt have dated and slept with Elena Gilbert.
- Both Damon and Matt have been flirty with Katerina Petrova (aka Katherine Pierce). However, Damon dated and slept with Katherine nearly a century ago. However, Katherine has only flirted, held a romantic attraction towards, and had nothing serious with Matt.