On The Vampire Diaries, Damon Salvatore's inner circle is pretty tight-knit and exclusive, and for five seasons, it doesn't include Bonnie Bennett. There's a lot of bad blood between the two, and both are guilty of trying to kill the other. Threats, intimidation and attempted murder isn't the basis for a long-lasting friendship.
Being trapped together in an alternate dimension for months is just the time out these two need to let bygones be bygones. As besties, Bonnie and Damon are ride-or-die... most of the time. Here are five times Bonnie and Damon's friendship were relationship goals, and five times they forgot to put the "fun" in dysfunctional.
Relationship Goal: Bonnie Frees Damon
Bonnie and Damon survive the collapse of the Other Side and four months together in the 1994 Prison World which cements their relationship as besties. Being super tight with a vampire with a shady past means Bonnie can murder Kai and ditch him without judgment. But getting rid of Kai proves more difficult, leaving Bonnie seriously injured. She makes sure Damon gets out while she stays behind on season 6's "The World Has Turned and Left Me Here." Bonnie always puts her friends first, and knowing her the arrow in her gut creates serious complications, she isn't about to deprive Damon and Elena of reuniting.
Not A Relationship Goal: Forces Bonnie To Face Kai
After finding out his mother is alive and living in another Prison World, Damon has no choice but to turn to Kai for help but Kai has a price: he wants to see Bonnie and make amends. Bonnie's struggling to adapt to life post alternate dimension and suffering from serious trauma thanks to Kai.
When Damon unwisely ambushes her with an unwanted reunion on season 6's "The Downward Spiral," Bonnie gets payback. She uses her powers to give Damon just the slightest taste of what she endured at Kai's hands. The one person she feels most connected to uses her, breaching the trust that was so difficult to build. It's one of the few times Damon is genuinely sorry for his actions and offers a sincere apology.
Relationship Goal: Damon Goes Back To Prison World
Damon's home and consumed with winning over Elena, but once he learns Bonnie is alive, he alienates friends and influences people to get her back. Damon returns to Prison World for Bonnie, twice. The first as a tangible ride home, and secondly, to save Bonnie from herself.
Months of solitude wears on the psyche, and Bon-Bon is ready to fill her lungs with carbon dioxide. Damon just needs to give Bonnie the key to getting out -- a little island off of Novia Scotia. Damon's selfless commitment to bringing people back from the brink only extends to Stefan, Elena, and Bonnie.
Not A Relationship Goal: Gives The Ascendant To Lily
Lily's only willing to help Stefan get his humanity back with some assurance from Damon they'll return to 1903 Prison World to retrieve her REAL family -- witch-pires and all-around nightmare, the Heretics.
Forced to keep his word to Bonnie or risk losing his brother to the dark side forever, Damon chooses door number two on season 6's "I Never Could Love Like That." This means handing over the ascendant to Lily, giving her the key to reunite with her friends and let Kai out of his alternate dimension lockdown -- the one he and Bonnie just left the Gemini coven leader. Just like that, Bonnie's sense of closure and safety go poof and puts her on Lily's radar. How many times can Damon do Bonnie wrong?
Relationship Goal: Bonnie Brings Damon The Cure
After helping Bonnie lock Kai in the 1903 Prison World on season 6's "A Bird in a Gilded Cage," Bonnie presents him with a thank you gift/souvenir from the 1994 Prison World -- the cure for vampirism. When Bonnie retrieves the magic that will bring her home, she grabs something Damon planned on going after himself. Bonnie doesn't lecture Damon about what to do with it, and she doesn't tell Elena. Bonnie leaves it up to Damon knowing he'll do the right thing. It's one of the few times someone gives Damon the benefit of the doubt, expecting a positive outcome.
Not A Relationship Goal: Damon Abandons Bonnie
Living an Elena-less life leads to so many bad choices, Damon decides to tap out. He's going to desiccate until Elena wakes up. This means leaving Bonnie behind for good. Damon doesn't even have the courtesy to break the news in person. Bonnie confronts Damon before he retreats from the world and calls him out on season 7's "I Would for You." Damon thinks he's saving everyone, but it's just hiding.
Bonnie and Damon don't have heart-to-heart chats, but this move makes her question if there's a friendship worth fighting for, and for Damon, it's not. Not to mention how many times he saves her life whether it's from Kai, oncoming traffic or severe head trauma. Bonnie needs a guardian angel just as badly as Damon needs her.
Relationship Goal: Bonnie Rescues Damon From Tyler
When Enzo traps Damon in a cell with Tyler whose about to go full-on wolfie, it's Bon-Bon to the rescue on season 7's "Moonlight on the Bayou." She has no magic, but she still manages to gain access to her bestie who's about to be ripped to shreds. Damon insists she leaves since Tyler can't differentiate between friend or foe when he's in his supernatural state.
But Bonnie refuses to abandon him, resulting in a nasty bump to the head that knocks her into a coma. This is the final straw for Damon who can't shake the feeling everyone he cares about most would just be better of if he wasn't around. As he sits by Bonnie's side in the hospital, he swears to do better by his second-best girl.
Not A Relationship Goal: Bonnie Tries To Stake Damon
Rayna transfers the life of the final Everlasting over to Bonnie, but as a final "screw you" to Damon, she gives Bonnie the unshakeable urge to kill vampires too. Damon believes he can talk his way back into her good graces and avoid the stake. Damon pulls out all the stops, but the one that solidifies them as one of The Vampire Diaries' epic friendships is Damon telling Bonnie he loves her just as Elena does. If that can't breakthrough b***h Bonnie, nothing can. But the urge is too strong, and there's a legitimate honesty in her hatred of Damon.
Relationship Goal: Damon Kills An Everlasting
The only way to save everyone from Bonnie, who is channeling a vampire huntress, is to go back into the Armory and destroy the final Everlasting. There's something wicked and nasty loose in the building that makes men lose their minds and their souls. Damon slaps on the hero's hair and decides to battle whatever comes his way just to give Bonnie her life back on season 7's "God and Monsters." He's still trying to make amends for his decision to desiccate, but the price for Bonnie's forgiveness turns out to be even higher than Damon anticipates. He saves the girl but makes a deal with the devil in the wake of this selfless act.
Not A Relationship Goal: Damon Tries To Murder Bonnie, Twice
Sybil can't stand any competition for Enzo's and Damon's attention, so she spends an entire day devising ways for Bonnie to die on season 8's "You Decided I was Worth Saving." Sybil sends Damon to do the job, but he gets his butt kicked by Caroline. Sensing Damon's heart isn't in the assignment, Sybil gives Bonnie an ultimatum: choose to save Enzo or Damon but not both.
Bonnie chooses Enzo, the man she loves even if it means sending Damon to hell. But Sybil isn't one for keeping her word, so Enzo's humanity switch goes off, and Bonnie is left defenseless and ripe to be torn apart by her best friend as her boyfriend watches. It's an all-time low when Bonnie gives up on Damon as readily as he gives up on himself.