In Dangerous Liaisons, Rebekah invited Matt to her family's ball as her dancing partner. He agreed and danced the traditional waltz with her. Later, Rebekah convinces Kol to kill Matt to make Elena suffer. She asks Matt to escort her outside telling him she needed a break from the party. While outside, he grabs his letterman jacket and puts it around her shoulders to warm her. Touched by his kindness, she changes her mind about killing him and the two go back inside before Kol can act.
She tells her brother that she doesn't want to ruin her mother's party. Kol chastises her for clearly liking Matt. Kol decides to follow through anyway, leading to Matt's hand being crushed before he is stopped by Damon. When Rebekah comes to Matt to apologize, he tells her to go away. Later, Rebekah meets Damon and hooks up with him because she's disappointed about Matt.
In The Murder of One, the Salvatores plan to kill the Originals, and one of the plans is to use Matt to kill Rebekah, though they later run into Finn and change their plan into just daggering Finn. Matt puts vervain in Sage and Finn's drinks; luring Finn outside to be staked.
In Heart of Darkness, Matt is busy keeping Rebekah involved in the 20's Decade Dance preparations so that Caroline gets a day off to meet with Tyler. He gives Rebekah a ride back to Klaus' Mansion and is sweet to her when he drops her off.
In The Departed, Matt was driving Elena home when Rebekah appeared in the middle of the road, forcing Matt to drive the car off the bridge and right into the river.
In The Rager, Rebekah sees Matt at school and invites him to her anti-curfew party, but Matt doesn't respond. Rebekah then says she never meant to hurt him but Elena after what they did to Klaus, Matt gives her a cold look and walks away. This later leads to a confrontation between the two. Rebekah ends up ripping Matt's heart out of his chest, but it is revealed it was just a hybrid-venom induced hallucination.
In The Five, Rebekah tries to get Matt to like her by buying him a new truck. He takes it but still doesn't forgive her. Klaus says she's trying too hard before telling her that the brotherhood of the Five still exists and wants her to come and help him, but she tells him she doesn't care about the Five, causing Klaus to leave.
Later, Matt discovers that April Young has become friends with Rebekah and tells her that he finds it hard to believe that Rebekah has any friends. When Matt walks away, Rebekah tells April, who is staring at him as he walks away, "Hey, off limits. I have dibs."
In The Killer, April comes into the Grill while Matt is working and asks him if he has seen Rebekah. April asks if he and Rebekah are a "thing," and he tells her that they are not.
In A View To A Kill, Matt overhears Rebekah telling Stefan that she wants to be human and find someone who loves her.
In Pictures of You, Rebekah approaches Matt at Prom and asks if he and Bonnie are a thing because they came together. He tells her no and asks her why she's here alone when she could've compelled herself a date. She then asks him if he thinks that she would make a good human. Matt says that "good" is a hard word to live up to; he tells her that he doesn't think she would because he has never seen her do a truly good thing. He says he's sorry and
walks off. Later, he asks her is she's seen Bonnie, which she hasn't. Rebekah then asks Matt to dance with her, which after some cajoling he agrees. On the dance floor, Rebekah tells him that he's right about her and that she will try to be good. He asks her why his opinion matters to her and she says that he's everything she wants to be. Matt says that he's just a busboy and she says that he's so beautifully human. When Rebekah learns Elena plans to kill Bonnie, she warns Matt. After Elena attacks April, Matt convinces Rebekah to save April with her blood. Matt then tells her that he won't tell anyone that she did and that he was too harsh earlier.
In She's Come Undone, Matt sees Rebekah in the Mystic Grill drinking shots. She tells him she's celebrating because she is free because Klaus and Elijah have gone off to New Orleans and left her alone.
Matt tells her that he's sorry she missed out on getting the cure. She says the she knew he was planning to steal it for Elena and that she never had a chance. Matt says that he meant that he was sorry. When Rebekah asks Matt to stay and have a drink with her, he says he has to meet Caroline. Rebekah says that Elena is fine the way she is and that they shouldn't try to fix her. Matt tells her that Elena was his friend long before she was her mean girl best friend. He asks her why she stays in Mystic Falls since her brothers ditched her and she lost the cure. He also tells her how he's broke, failing all his classes, and stuck in Mystic Falls before he leaves. Later, at the Salvatore Boarding House, Matt and Caroline are talking outside when Rebekah shows up. She brings Matt some burgers as a peace offering, which Matt gladly accepts. When Caroline tells Rebekah that they can't entertain, she volunteers to help Matt study since he mentioned that he's failing his classes. Surprised, Caroline asks why she didn't ask her to help him. Matt says that he didn't ask for Rebekah's help. When Caroline asks Matt what classes he's failing, Matt says that he's not failing, he's just "really, really behind" in history, Italian, and math. Rebekah suggests that she and Caroline help Matt. Caroline leaves to go home and get flash cards, study guides, and energy bars. Rebekah asks Matt, "You dated that?" and Matt replies, "She likes projects." Later, Matt is trying to use his AT&T phone to translate English to Italian. When Rebekah says it's handy but kind of a cheat, Matt tells her that not everybody has had 1,000 years to learn everything. She says that she was fluent in the 12th century but languages evolve over time. He tells her he doesn't want to get left behind while all his friends go to college. Rebekah tells him that the only reason he's failing is because he's been too busy with helping Jeremy and dealing with Elena. She tells him that he needs better friends, like her. She offers to compel him good grades and a scholarship. When he declines, she tells him that everyone in life needs an advantage and that she could be his. She tells Matt that when he convinced her to save April's life at the prom, she realized that she could be a better person and that she's grateful for that. She advises him to take advantage of her offer and make something of himself. She says that anyone who leaves him behind is a fool and that she wouldn't. When Katherine shows up and they learn that Damon is having her help get Elena's humanity back, Matt tries to call Caroline. Later, after Matt is killed while wearing the Gilbert Ring, Matt wakes up to find Rebekah with him. She asks if it hurt. Matt said that getting his neck snapped and rising from the dead hurt like hell. Rebekah tells him that Elena flipped her humanity switch back on and that she'll be back to her old self in no time. Rebekah tells him he did a brave thing; Matt tells her that he's paying her back for saving him from drowning. Rebekah says that she can't apologize enough for running them off the bridge or Elena becoming a vampire. She tells him that she will spend every day until graduation finding a way to pay him back.
In The Walking Dead, Rebekah is asking Matt about the purpose of graduation announcements in the Mystic Grill. They talk about their respective mothers and how no one will be there for them at graduation. Later, when the weird weather starts, they are still at the Grill along with Elena and Caroline. After Bonnie drops the veil, Rebekah and Matt are alone at the Grill, having a moment, when Kol shows up. Kol asks to know where Elena is so that he can kill her since Jeremy killed him. When Matt threatens him, Kol breaks a bottle in half and hurls it into Matt's shoulder. After Kol leaves, Rebekah offers to heal him but he refuses. He tells her that people in Mystic Falls have a habit of turning into vampires and that he wants to graduate high school as a human. Rebekah goes to look for a first aid kit in the back and finds Caroline, sitting on the floor compelled by Silas to keep cutting her wrists. Rebekah tries to snap Caroline out of the compulsion while Matt tells Damon that Caroline's been at the Grill the whole time. After Bonnie raises the veil, Matt thanks Rebekah on Caroline's behalf. She tells him that she's glad she got a chance to hit her. They see a man in the middle of the street, who Rebekah identifies as Alexander, her ex-boyfriend. When they turn around, Connor Jordan and Galen Vaughn are blocking their path.
In Graduation, Matt and Rebekah are outside Connor's RV with Alexander. Matt is standing on a pressure-sensitive trigger connected to explosives surrounding them. Rebekah asks Alexander to to let them go. He tells her that he's not holding her here, but Matt won't be able to leave the bomb trigger intact. Matt tells Rebekah to leave and that he will be fine; she says she's not leaving him. Rebekah follows the wires of the trigger, which are connected to bombs in the RV and several surrounding cars. Alexander warns her that even though she can survive, Matt can't. Matt tries to get her to ignore him by asking her what she plans to do after graduation. He tells her that just because he's never going to leave Mystic Falls doesn't mean that she can't see the world. She tells him that she's going to take him to places that he's only dreamed of seeing: China, Paris, Italy. She comments that they'll be alive and not miserable ghosts on the other side. This angers Alexander and he throws a dagger toward Matt; Rebekah catches it and stops Matt from falling. Later, Rebekah is holding up Matt so he won't fall off the trigger. Matt tells her that since he's wearing the Gilbert Ring, she could detonate the bombs and he won't die. She tells him that he'll be blown up along with the ring. He tells her there's only one way to find out. Rebekah appears to agree, then pulls Matt into a kiss and takes his place on the trigger. She tells him to run away and not miss graduation. When he runs away, Alexander angrily inquires what she's done; Rebekah replies, "I finally chose one of the good ones." She then vamp speeds away and the bombs detonate. Later that night, Rebekah shows up at the Lockwood Mansion to make sure Matt's all right. Matt says he'd invite her in, but he promised Tyler that he'd keep the house a low vampire zone. Rebekah tells him that because they were under duress, she understands if he doesn't want to travel with her. He tells her that they wouldn't work and that he wants to keep his love life a low vampire zone, too. She reluctantly tells him she understands and turns around to leave. Then, he tells her that whatever happens on the road stays on the road and that he doesn't want her changing him into a vampire. Matt tells her that he's never set one foot out of Mystic Falls, that he has no college plans, or what the future holds for him. He tells her that it's time to start living his life and what better person to show him how than her. Happily, she agrees.
In I Know What You Did Last Summer, Rebekah and Matt have spent the last 3 months traveling together. Elena mentions that they have sent postcards. When they first appear, Rebekah is handing Matt a glass of champagne while getting back into bed with him and a mysterious beauty named Nadia. Rebekah and Nadia kiss while Matt watches and smiles. When they return to Mystic Falls, Matt is seen tapping kegs for the end of summer party in the town square. Rebekah teases him about going from their travels to working again. Then, the two start making out and Rebekah suggests that she come with her to New Orleans. Matt tells her that he needs to work and make money. While making out, Rebekah tells him playfully not to call or miss her and she leaves.
Rebekah: "So I'm having a little party, you should ditch last period and come."
(Matt continues to ignore her and swap books out of his locker.)
Rebekah: "Look, I know you're still angry I ran you off the bridge, but you have to understand. Alaric killed my brother, he was trying to kill me, I had to do something to stop him. I never wanted to hurt you."
Rebekah: "Are they still keeping Elena trapped in the Salvatore mansion? I happen to like her just the way she is. It's tragic that they're trying so desperately to fix something that isn't broken."
Matt: "Elena was my friend long before she was your mean-girl sidekick. So if you're upset that you lost the cure and your brothers ditched you, why are you still in Mystic Falls? Some of us don't have the option of leaving, some of us are broke, and failing all of our classes, and stuck here. So why don't you take your freedom and get the hell out of town? I would."
Matt: "I just don't wanna get left behind when all my friends go to college and I'm the only repeat senior."
Rebekah: "The only reason that you are failing is because you're preoccupied with training doomed hunters and dealing with Elena's drama. You need better friends. Like me. I could compel you good grades and a scholarship.
Rebekah: "Why not? Everyone needs an advantage in life. I could be yours. When you convinced me to save April Young's life at the prom, I realized that I could be a better person and I'm grateful for that. So let me give you some advice. Take advantage of what I'm offering you. Make something of yourself. For the record, anyone who leaves you behind is a fool. I wouldn't."
Matt: "She saved me from drowning at the bottom of that river. I'm just doing what I can to pay her back."
Rebekah: "There aren't enough apologies in the world for the part that I played in this. Running you off the bridge, Elena becoming a vampire to save you. If you don't want me to cheat you into college, fine. We'll do it the hard way, but, Matt, I will spend every day until graduation trying to find a way to pay you back."
Alexander: "Go ahead, sweet Rebekah. Use your vampire powers to whisk him away. I'm sure you can survive the blast of six of these automobiles, but can he?
Matt: "Just ignore him. All right? Just think about something else. Like graduation. What are your plans? College? Travel? Just because I'm never getting out of this town doesn't mean you shouldn't see the world."
Rebekah: "It's just been settled. I'm gonna show you life as you've only dreamt it. We'll start in Italy. There's a lovely little church outside San Vittore in Brienno.