|“||You're my oldest friend. You're the girl that I've loved longer than I can remember... I know that still means something to you.||”|
Elena and Matt originally dated for the majority of high school until Elena broke up with him following her parents' deaths. He remained in love with her and was jealous when she began dating Stefan. Despite his new relationship with Caroline, he never got over Elena. They eventually were able to return to friends and confidants. After Rebekah made them drive off the bridge, Elena motioned for Stefan to save Matt instead of her, resulting in her transformation into a vampire. When Elena lost her humanity, Matt proved to be the only thing she cared about anymore as when Damon killed him, she broke down crying. However, thanks to the ring, Matt returned to life.
They are referred to as "Melena" by fans.
Kelly, Matt's mother, and Miranda, Elena's adoptive mother, were best friends during high school, which resulted in Elena and Matt sharing a crib as infants. They remained best friends as they grew up and began dating in their teen years. Eventually, Elena discovered she had fallen out of love with him. After a fight with Matt, Elena and her parents were in a car crash which killed them, resulting in Elena breaking up with Matt. Matt accepted her decision, hoping that they would eventually get back together.
When the school year started, Elena knew Matt was still upset about their break up and believed he hated her. During history class, Matt noticed Stefan staring at Elena and Bonnie text Elena about it. Matt asked Bonnie for advice involving Elena, but she just told him to give her time. Elena brought Stefan to the Mystic Grill and introduced him to Bonnie, Caroline and Matt. During the Back to School party, Matt told Elena he still believed in them and though she broke up with him because she needed some time to be alone, she didn't seem alone, as she was hanging out with Stefan. She told him she didn't want to hurt him, but he told her to do what she had to.
Tyler tried to embarrass Stefan in front of Elena to show her she "chose wrong" by attempting to hit him in the back of the head with a football, but was shocked when Stefan caught it before it hit him, surprising everyone and impressing Elena.
Bonnie told Matt to stop pining over Elena when they witnessed her and Stefan kiss. He later found out that Elena and Stefan broke up but saw they were still hanging out together. Matt and Elena began to reminisce about when they were kids together. Eventually, Stefan and Elena got back together and Matt started dating Caroline with Elena's permission. When Kelly returned, she disapproved of Caroline, and made a point of preferring Elena, calling Caroline a "rebound" and joking that Elena had broken Matt's heart. Caroline saw Matt looking jealously at Elena and Stefan together so organised a double date to see if he was still in love with Elena. Matt and Elena reminisced about their childhood memories on the date, making Caroline jealous. Matt later accidentally brought up how he and Elena had often made out in his car, making Caroline mad. Matt apologised to Stefan who brushed him off, claiming he understood that he had a history with Elena.
When Vicki's body was found, Matt was distraught. Caroline asked him if he wanted to talk but he refused her, claiming he just wanted to be alone. However, then Elena showed up and they ran to each other and hugged, upsetting Caroline as she realised he would always have a better connection with Elena than with her. At an event, they danced together, and after Matt's fight with Tyler, Elena treated Matt's wounds and comforted him.
While Elena and Matt are helping prepare for the Masquerade Ball, Matt asks Elena about Caroline, who he had just broken up with, and tells her he thinks she is seeing someone else. She tells him that Caroline isn't dating anyone, and tells him to give her time.
Matt helps Elena escort Jenna back home after she was compelled to stab herself by Katherine. Matt asks Elena if she's going to the ball. She says she isn't, as Stefan and her broke up. She asks him to stay the evening with her, Jenna and Alaric, but having been compelled by Katherine to activate Tyler's curse, he says there's something he has to do at the ball. He tells her he'll always be there for her, and leaves.
On a girls' night with Bonnie, Caroline and Jenna, Elena walks in on Caroline and Matt kissing, discovering they are back together. After discovering that Caroline is a vampire, Matt runs away. Caroline asks Elena for advice, but she says he was never one to run. Elena promises to help Caroline find Matt later but is unable to do so when she's kidnapped by Isobel.
During Senior Prank Night, Matt and Elena help set up pranks around school. When Klaus threatens to kill Tyler and Elena, Matt drowns himself so that he could contact Vicki on the other side and have Bonnie revive him. He learns that Elena's blood is needed to create hybrids, saving her life.
Matt and Elena planned Caroline's party but when Caroline showed remorse at not actually aging, they decided to throw a funeral instead so that she can move on from her human life. After Caroline goes missing, Elena and Matt go looking for her and find her, having been bitten by Tyler although Klaus heals her. Elena and Matt later go to Wickery Bridge and she confesses she feels like she let the real "her" down with the choices she has made. Matt tells her its okay for her to change and move on, throwing dandelions into the river as a symbol of her moving on to her new life.
Matt shows up to comfort Caroline after her father's death as Elena watches them together. Matt walks Elena home where they discover there's a power cut. They arm themselves but find Alaric who has been attacked. Elena kills him so that he can come back as Matt watches in horror. Elena asks Matt to stay with her until Alaric wakes up, confessing she can't lose anyone else. Matt promises he'll stay and they wait by Alaric's body.
Matt and Jeremy struggle to protect Elena and Matt drugs her tea so that she will fall asleep and begins to leave town with her. They later receive news that Klaus is dead. Matt tells Elena that they can drive to Damon 100 miles away or head back to Stefan, Caroline and Tyler, and she chooses the latter, calling Damon to inform him of her choice. Elena then sees Rebekah in the middle of the road and yells for Matt to look out. He ends up swerving off the bridge. Stefan arrives to save Elena but she gestures for him to save an unconscious Matt first. As Stefan saves Matt, Elena dies.
Matt, who feels guilty about Elena becoming a vampire to save his life, tells Damon he will help him free her when Pastor Young captures her, Stefan and Rebekah. Damon takes him to Pastor Young's ranch where they're being held in cow pens. Damon, angry that Matt gets to live and Elena died, goes to kill Matt, who tells him that he can't hate him any more than he hates himself. Damon is about to kill him when Elena attacks him and tells him to leave Matt alone. When Elena struggles with her urges after Connor attacks April, Matt offers for her to feed on him to satisfy her thirst. Matt continues to offer his blood to Elena, saying he owes her his life.
Elena and Matt head to their old make out spot at school where she feeds on him carefully. Matt later shows up at Elena's where he apologises to her. Elena admits to feeling angry ever since she turned, especially toward Rebekah, and says she's hungry. Matt lets Elena drink from him and she almost ends up killing him until Damon shows up and compels him to forget it.
When Jeremy is awakened as a member of the Five, he begins to experience dreams in which he kills Elena. Matt becomes worried by this and insists Jeremy tell Elena. After Jeremy attacks Elena, Matt tries to stop him until Stefan shows up and tells Matt to take Jeremy home. Elena moves in with Damon and Matt moves in with Jeremy. When Elena and Stefan return from the island with a dead Jeremy and no cure, Matt arrives to comfort Elena and they hug each other for comfort. Matt takes Elena to the "stoner pit" where they find grafitti by Jeremy and Vicki. Matt tells Elena its okay to have hope.
Matt and Elena meet again at the prom. Although Elena insults Bonnie, she seems indifferent to Matt. After discovering that Stefan and Damon are getting Katherine to torture Elena's emotions back into her, Matt declares that he's going to find Caroline and angrily yells that he's not letting "that psychopath" in with Elena. After Elena escapes, Damon tells Matt to come with him to find her. When Matt finds her in the woods, she's grateful, and demands she feed from him. He tries to stop her and she's irritant with him. Damon and Stefan then show up and Damon tells Elena that she will be upset if they kill Matt. She accuses them of lying, but Damon kills him, causing Elena to break down crying, meaning that Matt was the person she cared most strongly about even with her humanity off. Elena's relieved to discover that Matt was wearing Jeremy's ring. When Matt woke up, Rebekah commended him for his bravery, but Matt said that it was the least he could do as Elena died to save him. He's relieved that she regains her emotions. They later graduate together.
- Elena: Well, we were wasted; that was the first time I ever got drunk. I blamed Matt.
- Matt: Her parents got seats at the next booth.
- Elena: And Matt had me pretending that I was choking so we can get away...
- Matt: Except that her dad was a doctor so he jumped out to save her.
- -- There Goes the Neighborhood
- Matt: So, where’s Caroline? This is like her thing. I can’t believe she’s not here.
- Elena: She has something else to do.
- Matt: Is she seeing someone?
- Elena: Matt, come on. No, she’s not.
- -- Plan B
- Elena: You look good in a suit.
- Matt: You and Stefan will work it out.
- Elena: I don't think so, Matt. There's so much about me and Stefan that'll never work.
- Matt: You know I'm here for you, always.
- -- Masquerade.
- Matt: Hey guys.
- Elena: Matt, hey... [He kisses her on the cheek]
- Matt: Happy birthday.
- Elena: Thank you...
- -- The Birthday
- Matt: You're not that girl anymore. It's okay if you want to let her go.
- Elena: Is it? 'Cause I feel like I disappointed her a little like I disappointed them. My parents.
- Matt: For me to say, as a guy who knew that girl, you're doing better than you think. Here lies Elena Gilbert. A girlfriend, and an amazing friend.
- -- Our Town
Matt was a good friend of Elena's and when they started dating it didn't feel right as she thought of him as a brother. At the start of the school year, Elena was immediately drawn to Stefan. Elena broke up with Matt, feeling that the relationship between them wasn't anything more than a friendship. Matt believed it was because of Stefan that their relationship ended. Tyler was being rude to Stefan but Matt saved him, offering for him to take part in tryouts. Whilst trying to get away from Elena, Stefan accepted Matt's offer.
Elena was hurt but decided on a new plan with Meredith and Bonnie, creating a rumour that Elena had met a Frenchman while on her vacation in France named "Jean-Claude" (but the photo she showed was actually the gardener who had two kids). Matt was hurt by the rumour as it meant that Elena was with someone else while she was with him. Realising how he felt, she told him the truth about the rumour so that no one would think she was upset by Stefan's rejection. Matt accused her of only caring about herself, hurting Elena, and Matt apologised. She asked him to invite Stefan to the homecoming dance and he agreed to.
After being crowned Homecoming Queen, Elena left the party with Tyler, Dick and Vickie. Meredith, Bonnie and Matt went to look for her, finding Vickie in hysterics after being attacked. Matt was at Elena's house when she showed up with Stefan who had saved her from Tyler.
After Stefan started dating Elena, Matt's friendship with him became strained. After Mr Tanner's death, Stefan was accused and Elena, worried, sent Matt to look for him. Matt found Stefan unconscious in the locker room and told him what happened. Stefan left, having Matt make a promise to protect Elena.
Matt kept his promise to Stefan to look after Elena after Stefan disappeared. Elena, still upset that Stefan was missing, pushed Matt away but Matt watched from a distance. He followed Elena, Bonnie and Meredith to Wickery Bridge and helped figure out Stefan's true location. They rescued Stefan and while Matt insisted that Stefan go to the hospital, Elena convinced him to take Stefan back to the boarding house.
- They kissed for the 1st time during their high school freshmen year.
- Matt's name was changed from Honeycutt in the books to Donovan in the series.
- They are exes in both the books and the series, however they are together at the start of the books and at the start of the series they have been broken up for several months.
- They are each other's "firsts".
- Elena's brother, Jeremy, dated Matt's sister, Vicki.