Life sucks when you're ordinary. And what makes you exactly not like them? You're a vampire. You take that cure and become human, you're no one, nothing. Trust me, losing this cure was the best damn thing that ever happened to you.
In Smells Like Teen Spirit, Damon gets introduced to Rebekah as Klaus has left her behind, after finding out that Damon has found Mikael. Elena asked Damon to keep an eye on Rebekah so that she can get Stefan to turn on his humanity again. Rebekah coyly tells Damon she knows he’s trying to distract her— then, after telling him no fight between the two of them could ever be fair, she stabs him right in the gut.
In Dangerous Liaisons, Rebekah went to Matt to apologize for what happened to him but Matt told her to leave him alone. Damon arrived to find Rebekah standing at the bar so Damon poured them both a drink. Damon tells her that she needs someone that is more durable, and Rebekah asks him who that would be. Damon and Rebekah are next seen in his bedroom, kissing and ripping off each other's clothes madly. Damon and Rebekah then have sex.
In All My Children, Elena visits Damon to apologize for what she said to him, but Damon claims that he is over it. Elena stands there shocked when she sees Rebekah standing next to Damon. Rebekah then walks past Elena with a smile on her face.
In 1912, Damon arrives at the mystic grill and sees Rebekah talking to Carol. After Carol tells Rebekah that the Salvatore owned the mills back in the day, she went over to Damon and Stefan to talk about it. Later when Rebekah catches Damon's dart, she tells Damon that Sage knew Finn 900 years ago. When Stefan leaves the bar, Damon and Rebekah force him to feed on a girl in the street as a test to see how much blood he can handle at a time. Stefan drinks, and just about drinks her dry like he did in 1912 but Damon stops him. Damon tells Rebekah to leave.
In the episode Break On Through, Sage convinces Damon to get close to Rebekah to find out why she is asking about the trees. Damon seduces Rebekah and the two end up kissing and having sex again. While Rebekah is sleeping, Sage comes into Damon's bedroom and goes into her mind, only to find out that there is another white oak tree. Damon looked at the old 1912 log book and finds that they used the white oak tree to build thewickery bridge. Sage tells Rebekah about the bridge and she is seen burning the parts used on the bridge. Damon asked Sage why she betrayed him, and she replied that he didn't tell her that Finn and the other Originals were bound together. However, Damon finds a sign which was made of the white oak tree's wood and they can now kill the Originals.
In The Murder of One, Rebekah tortures Damon after feeling betrayed because he pretended to like her and used her to get information on the White Oak Tree. Later, after Stefan tries to bargain the remaining White Oak Stakes for Damon's freedom, Rebekah lets Damon go even though they don't have all the stakes as a sign of faith. When Klaus comments on this, Rebekah responds that she respects the Salvatore's because they are willing to fight for each other and die for each other, which is more than she can say for Klaus.
In The Departed, when Rebekah comes to see Damon at the storage warehouse, Damon hides Rebekah and tells her to be quiet. The two then try to get Klaus' body out of the storage warehouse before Alaric finds them. Alaric shows up however, and stakes Klaus, with an emotional Rebekah watching. Just as he is ready to kill Rebekah, Damon yells at Rebekah to run, showing that he does in fact care about her.
In Growing Pains, Rebekah was looking through some old drawings of Klaus' when Damon shows up with a white oak stake. He tried to attack Rebekah but she pushed the stake out of his hand. Damon ran when Rebekah was shot with wooden bullets.
In Down The Rabbit Hole, When Rebekah and Damon are in Silas's cave, Vaughn attacks them. He escapes after Stefan arrives, in which Damon tells Stefan to go help Elena. Damon then revives Rebekah. Rebekah tells him that he loves Elena and he always will and he will never find peace with the fact that she may not feel the same way as a human. She also tells him that he did something selfless and he's becoming a halfway decent person.
In Bring It On, Damon walks over to Rebekah and explains to her that she is different from most people because she is a vampire. He also tells her that losing the cure was the best thing that has happened to her because if she took it, she'd become human and be a nobody.
In American Gothic, Damon, Rebekah, and Stefan go pay a visit to Katherine Pierce in an effort to find the cure. When they acquire the cure from Katherine's apartment, Damon tries to talk Rebekah out of taking the cure but she ends up drinking it. They then discover that the "cure" was just a fake and that the real one is still out there.
Damon: If there's one thing that's a guarantee in this miserable, little world is that Katherine Pierce is gone. We need to find Bonnie. Oh! And beware of the immortal Silas. He was asleep in that cave, he's awake now.
Rebekah: I'm not a scaredy cat. My brother Kol drove himself mad worrying about Silas rising. It would benefit us all to be a bit concerned. And you're one to talk about being afraid, you're also scared. You're 1,200 miles away from where you're supposed to be.
Rebekah: Stefan could've done that. Aren't you Elena's current love? It's hard to keep track these days. Shouldn't you be home comforting her? Or are you terrified of being there when she realizes that her brother's dead?
Damon: (Suddenly grabs Rebekah and she gets shot by an arrow)
Rebekah: He's right. We can't kill him. But that doesn't mean we can't tear him apart. Piece by piece. Nerve by nerve. Till the pain is so severe that your brain shuts it off to give you one tiny moment of blessed relief. And then we'll heal you, and do it again and again and again.
Rebekah: Really? Why? I heard your little chat with Stefan. I know Elena's broken the sire bond. So, why would you wanna find the cure? You'd just cure her back to loving your brother. I think you're best off leaving it for me.
Rebekah: Well, nobody could ever mistake you for subtle.
Damon: You have to take pride on your work. (To the girl he fed on) It's okay, come here, come here. (Compelling her) Now, I want you to walk very slowly to your car... off you go.
Rebekah: You know, I just don't see how this increases our odds any.
Damon: I've been on the other side of a wolf bite. First, you get really sick and you get really hungry. When the sun's gone down, imagining he's gonna be looking for his last supper. I just laid out a three course 115 pound meal for him.
Rebekah: You killed him to prevent me from finding Katherine to keep me from getting the cure.
Damon: Do you really want the cure? I mean, really. Look, let me give you a little bit of advice. See these girls--they look happy. Now, in five years, they're gonna settle from mediocre starter husband and a mind-numbing career. And about that time, they're gonna realize something you're never gonna have to learn.
Damon: Life sucks when you're ordinary. And what makes you exactly not like them? You're a vampire. You take that cure and become human, no, you're no one, nothing. Trust me, losing this cure was the best damn thing ever happened to you.
Damon: Whoa, whoa, hang on. We need her alive. The cure is not here. You check upstairs, I'll check down. I got this. So, if I was a paranoid, distrustful sociopath, where would I keep my prized possession.
Damon: Because I'd want it to be close, but not on me. Accessible, but not obvious. I wanna keep it safe, but not so safe that I'd be too difficult to grab and run. Well, that is a fancy little treasure chest. In a tank with no fish. I think I'm gonna have to check that out. Aah! Gah! Vervain water. Looks like we have a winner.
Damon has various of nicknames for Rebekah due to her cruel nature. (Barbie Klaus)
Even though they're enemies, Damon has saved Rebekah's life on numerous occasions, hinting that he might care a little for her.
Rebekah is the second character of three to have sex with both Salvatore Brothers, Stefan in the 1920's and 2011,Damon in 2010, the first Character being Katherine and the third being Elena.
Damon met Rebekkah in the episode Smells like Teen Spirit.
They had a one night stand and Elena was jealous and mad.
Damon was one of the many people who tried to talk Rebekah into not taking the cure, although instead of using threats like Klaus or thinking of it as a test like Elijah, Damon showed her what her future could be like without vampirism.