The relationship between Damon Salvatore and Bonnie Bennett started in the episode History Repeating, when Damon sought to get the Bennett Talisman back from Bonnie to open the tomb that Katherine was locked in for 145 years (or so he believed). Their relationship improved during season 2; Damon and Bonnie worked together to help protect and save Elena. In season 3, Damon helped Bonnie find her mother, Abby Bennett Wilson, who they believed could help open the coffin they stole from Klaus that was spelled shut. Shortly afterwards, Damon made a last minute decision to turn Bonnie's mother into a vampire in order to break the spell that was allowing Esther to channel the entirety of the Bennett witch bloodline, living or dead. Esther was planning on killing all of her children, and Damon and Bonnie were trying to intervene in order to protect Klaus' vampire bloodline (from which Damon, Stefan, Caroline, Tyler and Abby were turned).
Ever since the episode, Stand By Me, Bonnie seems to like Damon better now because he was the only one who stayed on the island just to find her.
The possibility of a romantic relationship between the two is referred to as "Bamon" by fans.
In History Repeating, Bonnie had multiple dreams about her wiccan ancestor Emily, which lead the girls (Elena, Bonnie and Caroline) to decide to hold a séance. During the séance, Emily Bennett was able to possess Bonnie and use her own more mature powers to destroy the Bennett Talisman and try to prevent the release of the vampires sealed in the tomb under Fell's Church. Meanwhile, Damon reveals the reason he really came back to Mystic Falls: to resurrect Katherine with the help of the talisman, which Katherine had given to Emily on the last day of Emily's life before she was executed. Stefan tried to stop Damon, knowing that it would cause a disaster in Mystic Falls: all the vampires held in the tomb of the old Fell's Church were trapped without blood for 145 years, which caused them to desiccate slowly and painfully, and Emily was concerned that the vampires would kill the descendents of the Founding Families in retaliation.
On her way to the ruins of old Fell's Church, Damon greets Emily (in Bonnie's body) and reminds her about the deal they made a century and a half prior: Damon would protect Emily's line and Emily would protect Katherine. Damon lunged for the crystal talisman, and Emily used her power to throw him up to the branch of a tree so she could perform the ritual to destroy the crystal without his interference. Emily released Bonnie from her possession immediately afterwards. Furious, Damon attacked Bonnie, but Stefan saves her by pulling him off of her and feeding her his blood to heal her.
In Isobel (episode),Isobel and John Gilbert (Elena's biological parents) want the Gilbert Device, which Pearl stole back in 1864 from the original Johnathan Gilbert. Pearl gave it to Damon, and when Isobel and John found out, Isobel demanded that Elena, Stefan and Damon give the device to her or would kill Jeremy. Bonnie, after she learns the device is a weapon against vampires, offers to de-spell the device, which would make it useless. However, she only pretended to de-spell it because of her dislike of vampires (excluding her friends who were turned into vampires, such as Caroline). However, Bonnie makes up for it in the end by helping Elena and Stefan save Damon from death.
In The Return, Caroline is admitted to the hospital after she, Tyler, and Matt are in a car accident. Bonnie arrives at the hospital feeling extremely guilty and worried about Caroline's condition, as the wreck occurred due to Tyler being affected by the noise of the Gilbert Device that she lied about deactivating. Still, although with resentment toward Damon, she convinces him to giving Caroline some of his blood to heal her and guarantee her recovery.
In Brave New World, after Caroline is murdered by Katherine in the hospital, Bonnie is horrified to discover that Caroline has transitioned into a vampire. This caused Bonnie to lash out at Damon, who she blamed for all the misery that had occurred in Mystic Falls, and uses her powers to spray Damon with water from a hose and then set the water on fire. She was determined to get rid of Damon once and for all, but Bonnie is stopped by Elena, who reminded her not to let the vampires get the best of her.
In Plan B, Bonnie bumped into Mason and got a vision of him and who she thinks is Elena (but is really Katherine) kissing. Stefan realized what it meant, and informed Damon. Together, Bonnie and Damon incapacitate Mason and take him back to the Salvatore Boarding House where they try to find out where the moonstone was and what he and Katherine wanted with it. Bonnie, who Damon calls "Judgy", leaves as soon as she learns that the moonstone is in a well, and leaves Damon before she can find out what Damon planned to do with him.
In Masquerade, Bonnie helped Damon and Stefan with their plan to kill Katherine at the Masquerade Ball by putting a spell on a room in the Lockwood Mansion to keep vampires inside.
In The Sacrifice, Bonnie did a spell to help Damon and Stefan.
In Know Thy Enemy, Bonnie worked with Jeremy and Damon in order to find the spell they needed to harness the power of the one hundred witches killed in a massacre hundreds of years prior. Damon admitted knew where the site was because Emily Bennett had been burned there, and that he had tried to save her. He took them to the site where the witches were burned. Inside the house, Damon noticed that he could not move. Seconds later, his daylight ring stopped working, and Bonnie deadpans that the spirits didn't like him being in the house. Stefan and Damon later called Bonnie "their secret weapon" because no one except for them knew that Bonnie had her powers back and had been successful in harnessing the energy of the 100 dead witches.
In The Last Dance,Bonnie and Damon at the 60's decade dance
Bonnie and Damon figured out that Klaus (in Alaric's body) had been planning to kill her by provoking her into using more magical power than she was able while trying to kill him. Damon told Elena to run and find Stefan, and then asked Bonnie if she was still willing to do what has to be done to kill Klaus. When Stefan and Elena returned, they found Damon alone and Bonnie in the cafeteria fighting with Klaus. After a few striking blows at Klaus, Bonnie sank to the ground and Stefan and Elena couldn’t find a pulse. Damon cut in and told them to leave and that he would take care of the body, stating that the Sheriff couldn't find out about it. He took Bonnie back to the house on the witch burning site and she woke up soon after, revealing that she had only pretended to die in order to give the group more time to formulate a plan to kill Klaus. Damon and Bonnie decided not to tell anyone because the only way that Klaus would think she was dead was if everyone else did as well.
Bonnie and Damon leave after trapping Alaric and others in the house
In The Sun Also Rises, Bonnie cast a spell on John to bind his life-force to Elena's. Damon, Bonnie and Elijah leave for the sacrifice, where Klaus was planning on killing a vampire (Jenna), a werewolf (Jules) and the Petrova Doppelgänger (Elena). Jeremy wanted to accompany them, but Bonnie kissed him and cast a spell to make him pass out. Meanwhile, Alaric was furious when he discovered that he was unable to leave the house, due to the sealing spell Bonnie had placed on the house to keep him and Jeremy safe. Bonnie appeared and threw Klaus across the ground. Greta headed over toward them, but Damon broke her neck. He picked up Elena and pulled the stake out of Stefan's back. Stefan told him to get Elena out of there and revealed he won't leave until Klaus is dead. Bonnie continued to cast the spell and as Klaus weakening, Elijah approached him. Elijah began to kill him, but Klaus croaked that he did not bury their family at sea - the bodies were safe. He promised to take Elijah to them if he saved him, and told him that if he killed him, he would never find them. Bonnie threatened to kill them both if Elijah doesn't slay Klaus, adding that she didn't care if she died in the process. However, Elijah apologized and dashed away with Klaus before Bonnie could stop them.
In Homecoming, Bonnie attacked both Tyler and Damon with aneurysm spells in order to stop them from fighting each other. Bonnie stopped Damon from killing Tyler (out of fear of the implications of Tyler's sire bond to Klaus) and learned that Damon had the weapon that could kill Klaus.
InThe Ties That Bind Damon helped Bonnie find out where her mother was living, so they could ask for her help to open Klaus's sealed coffin (that was later revealed to hold Esther). Bonnie discovered something different about how Damon and Elena act with each other. After Elena won an argument with Damon, Damon told Bonnie that they kissed, leaving Bonnie shocked and giving Elena a quizzical look.
In "Down the Rabbit Hole " when Shane (Silas) claims that he will stay on the island to find Bonnie, Damon stays along to make sure he'll do it, while Rebekah stays to find Vaughn.
In "Stand By Me," Damon left Vaughn with Rebekah, so she could pursue her lead on the cure, and he was off to find Bonnie. Luckily, Bonnie walked out of the woods and found Damon, who hugged her. Bonnie and Damon drove up to Elena's house, and Damon immediately told Caroline to get him Stefan. Apparently Bonnie had shared her plan with him on the trip home. Damon told Stefan about how Bonnie needed to complete the Expression Triangle in order to gain enough power. She mentioned about droping the veil between this side and the Other Side, so all supernatural creatures have access and they can all see Jeremy, Alaric, Vicki and everyone that they ever lost.
Damon: Yes, Bonnie, I would love to know why a non-vampire was tortured by the vampire torture device that you let John Gilbert use against us. Speaking of your guilt, how's Caroline?
Bonnie: I told you: I only get what I get (Mason grabs Bonnie's arm and she screams. Damon pulls her out of Mason's grasp) That's it. That's all I got (Walks quickly up the stairs).
Damon: Hey, Judgey? (Bonnie turns around to look at him) Thank you.
Damon: You're still mad at me for what happened to Abby. Let me apologize. I'm sorry Elijah forced us to turn your mother into a vampire to save Elena's life. Didn't exactly have a choice.
Bonnie: There's always a choice. Whenever you make one, someone else suffers.
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