|“||Hypothetical Question: If Jeremy Gilbert's life was hanging by a thread, could I credibly just let him die? Because his death would be really convenient for me.||”|
Jeremy officially met Katherine for the first time in Masquerade, while she was posing as Elena. He wasn't fooled by her act, and knew who she really way. He delivered a message to her from Stefan and Damon, and told her that they were ready to hand over the moonstone. When Katherine asked him why they would send him as a messenger, he informed her it was because they knew that he wasn't afraid of her.
He met her again in The Sacrifice, when he tried to retrieve the moonstone from the tomb she was locked in, underneath the ruins of Fell's Church. He successfully retrieved the moonstone; however, she attacked him and fed on him until Stefan eventually saved him.
In The Reckoning, Katherine kidnapped Jeremy when she found out from Bonnie that Jeremy could contact Anna, as he is a medium. She decided to use to get information from Anna about Mikael. After they got the information, Katherine and Jeremy became partners in order to find Mikael in the cemetery in Charlotte. When they reached the cemetery, Katherine tries to awaken him by using blood from various animal and human sources, but it doesn't work. Later, after Mikael fed on Katherine and drained her, it is presumed Jeremy told Mikael to look for Klaus in Mystic Falls, and helped Katherine after she was drained.
In Down The Rabbit Hole, Jeremy and Bonnie discovered Silas' tomb. Then, Katherine, who was disguised as Elena, came into the tomb to grab the cure. The only way she could do this was to awaken Silas, so, Katherine bit Jeremy, fed his blood to Silas, and then grabbed the cure before taking off. Once Silas was finished feeding on Jeremy, he snapped his neck, which killed him.
In I Know What You Did Last Summer, Damon returned home to the Salvatore Boarding House just after Silas had attempted to kill the now-human Katherine. Damon pushes Katherine toward the now-alive Jeremy, and orders him to take Katherine somewhere, and warns him not to tell Damon where he's going, due to Silas being able to read his mind. Jeremy drove Katherine away, but because Silas threatened Stefan in order to motivate Damon into returning Katherine, Damon ultimately called Jeremy and instructed him to bring Katherine back. Katherine catches on to what Jeremy was told to do after he turned the car around, and once she learns that Jeremy won't protect her, she tugs the steering wheel out of his hands and drives them into a utility pole. Jeremy was severely injured and lying in the road, but Katherine chose not to help him in order to get away before Silas could find her.
In True Lies, Matt and Jeremy were sent by Damon to find and catch Katherine. They found her when she was assaulting a woman who was spying for Silas, and they tie her up and drive Katherine away in order to hide her from Silas. Katherine, who had come down with a cold for the first time since she was a human in the 1490s, repeatedly complained about her illness, and managed to convince them to get her some medication at a gas station. The boys allowed her to use the restroom, but once they were occupied, she tried to run away from them. She was spotted by a gas station attendent who was also compelled to spy for Silas, so Matt knocked him out in order to give Jeremy time to find Katherine and get them all out of there.
They drove her into the woods and set up camp. Katherine was sitting by the fire, and saw a shotgun across from her. Jeremy noticed her her eying the shotgun, and tells her to not even try it. Katherine responded that she had never fired a gun in her life, as she was much more deadly when she was a vampire. Some time later, Katherine was still by the fire, trying to warm herself as she recounted all of the terrible things she had managed to survive. Jeremy felt sympathy for her, so he walked over and draped a blanket across her shoulders, which did not go unnoticed by Katherine. They heard Matt telling Jeremy to run from the woods when Silas had found him, and he grabbed Katherine and ran off with her. They ran toward the truck, where Jeremy threw her Matt's keys and instructed her to drive off without him. She hesitated and asked where he was going. When he reminded her that he needed to find Matt, she warns him to look out for himself--she tells him that the only reason why she survived for 500 years was because she only thought of herself. Jeremy retorted that this was the reason why she was always treated like an object, rather than a person, and ran off without her.
Jeremy headed back towards the woods, where he found Matt's body, he has a broken neck when Silas suddenly appears. Silas realized that the Gilbert ring kept Matt from dying, and after a moment, the two began to fight. Jeremy was a better fighter, but eventually, Silas gained the upper-hand by stabbing himself through the chest in order to stab Jeremy as well. As Jeremy collapsed onto the floor, Silas raised the hatchet to finish him off, but is interrupted when he is shot in the chest. Jeremy looked behind him to see Katherine with their shotgun in her hand, having saved his life. He tells her he thought she didn't know how to use a gun, but she quipped that she figured it out, and shot Silas again.
- Katherine: What is it Jeremy?
- Jeremy: I have a message from Stefan.
- Katherine: Oh?
- Jeremy: He and Damon want you to meet them at the edge of the lake by the woods. They brought the moonstone.
- Katherine: And why are you their little messenger?
- Jeremy: Because they know I'm not afraid of you.
- Katherine: Hmm, you Gilbert men, so courageous. How's John by the way? Were they able to sew his fingers back on?
- Katherine: The youngest Gilbert. This is an intriguing surprise.
- Jeremy: I’m here for the moonstone.
- Katherine: Yeah, yeah, the moonstone. It’s very popular today.
- Jeremy: Just give it to me.
- Katherine: Naïve little Gilbert. If you want it, you’re gonna have to come here and get it.
- Jeremy: This isn't going to work.
- Katherine: I think that your witchy girlfriend's worried that you've run away with your ghostly lover.
- Anna: They're looking for Mikael.
- Jeremy: Mikael!
- Katherine: Mikael. Is that his name?
- Damon: Who's Mikael?
- Anna: The vampire who hunts vampires. You don't want to wake him. He will kill all of you.
- Damon: What's she saying?
- Katherine: Hello!
- Jeremy: He's a vampire and a Hunter, and you guys would be idiots to wake him.
- Damon: Don't fall asleep, Jer. You might have a concussion.
- Jeremy: Thanks for the concern, dick.
- Katherine: Oh, stop pouting. He took one for the team. Everyone back home will thank you once Klaus is dead.
- Katherine: Come on. We gotta get you up.
- Jeremy: You have to help Bonnie. The hunter stabbed her. You have to feed her.
- Katherine: Okay. I just need to make sure that you're okay first.
- Jeremy: I'm fine. What are you doing?
- Katherine: The cure. Jeremy, after everything we've been through, it's right there.
- Jeremy: It'll be there after we help Bonnie.
- Katherine: God, I forgot what a brat you were.
- Jeremy: What?
- Katherine: I'm done playing nice. (She opens Jeremy's wrist and feeds it to Silas)
- Jeremy: Katherine.
- Katherine: It's been too long, little Gilbert. Sorry. Family reunion is gonna have to be cut short.
- Katherine: Where are we going?
- (She is ignored)
- Katherine: Are you deaf? I said where are we going?
- (Damon calls Jeremy)
- Jeremy: Hey.
- Damon: How far'd you get?
- Jeremy: You said not to tell you.
- Damon: You pick now to listen to me?
- Jeremy: We just passed Old Miller Road.
- Damon: Good. Turn around, bring her back.
- Katherine: What? No!
- Katherine: What are you doing? Jeremy, stop! You can't take me back there, Jeremy. Damon wouldn't just hand me over. Silas clearly got in his head.
- Jeremy: Shut up, Katherine!
- (Katherine jabs her hand at Jeremy's seatbelt buckle.)
- Jeremy: Hey, what the hell!
- (Katherine grabs the wheel and drives them into a utility pole. After a while Katherine stumbles outside of the car while Jeremy lies on the ground)
- Jeremy: Hey. Please.
- (Jeremy struggles to breathe and reaches a hand out toward her. She turns and hobbles away.)
- Katherine: Are these ropes really necessary?
- Jeremy: Bullet would've been more effective, but we're trying to be nice. You crashed my car and left me to die.
- Katherine: You were gonna hand me over to Silas to get Stefan back. I was just protecting myself.
- Matt: How many people have you killed using that excuse? Just be glad we got you some clothes.
- Katherine: Don't play the hero. You two are just waiting for the convenient time to hand me back over to him. I've done this a thousand times. I get it. I'm the leverage; I'm that thing that everybody wants. I'm the freaking moonstone.
- Katherine: Ugh. Thank God, we're stopping. If I can only get out of the car.
- Matt: Well, you can't, because as soon as we get gas, we're getting back on the road.
- Katherine: Ugh, but I'm dying back here.
- Jeremy: You're not getting out of the car because you want an aspirin.
- Katherine: Then maybe I can get out of the car because I need to pee? Like, in a bathroom. Like a lady.
- Jeremy: Hurry.
- Katherine: My throat is really scratchy, and my head hurts, like, right here. When I cough, it's green. So, get me some stuff for all that.
- Jeremy: Silas knows I'm with you. Sorry, I can't risk being seen.
- Katherine(to Matt): Please.
- Matt: Fine.
- (Katherine is sitting at the campfire, looking at a shotgun.)
- Jeremy: Don't even think about it.
- Katherine: Please. I wouldn't even know how to use it. I've never shot a gun in my life. Didn't need to—I was much more deadly.
- Jeremy: Keyword: was.
- Matt: I'm gonna go get some wood for the fire. I'll be back.
- Katherine: I survived childbirth, the death of my entire family and 500 years of running from an immortal hybrid. You can understand why I'm a little upset that I'm on the verge of being defeated by a sinus infection.
- (Jeremy walks over to Katherine with a blanket and wraps it around Katherine, surprising her.)
- (Katherine and Jeremy run to Matt's truck and he tosses her the keys)
- Jeremy: Get in the truck and drive.
- Katherine: Where are you going?
- Jeremy: I can't leave Matt.
- Katherine: Wait. How do you think I survived 500 years? It wasn't because I was a vampire, it's because I never looked back. Don't be dumb. Survive.
- Jeremy: That's why people treat you like an object and not like a person.
- (Silas attacks Jeremy and stabs him with a tree branch. Silas picks up a hatchet and about to strike at Jeremy when Katherine arrives and shoots him with a shotgun.)
- Jeremy: I thought you didn't know how to use that.
- Katherine: I figured it out.
- Katherine was responsible for Jeremy's death.
- Even if they aren't biological siblings, they're both part of Elena Gilbert's family. Katherine is Elena's maternal ancestor and Jeremy is Elena's paternal biological cousin and adoptive brother.
- Jeremy has never commented on or acknowleged Katherine and Elena's similarities.