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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.

On a girls' night with Bonnie, Caroline and Jenna, Elena walks in on Caroline and Matt kissing, discovering they are back together.

However, then Elena showed up and they ran to each other and hugged, upsetting Caroline as she realized he would always have a better connection with Elena than with her.She tells him that Caroline isn't dating anyone, and tells him to give her time. 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.Matt helps Elena escort Jenna back home after she was compelled to stab herself by Katherine. He tells her he'll always be there for her, and leaves.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.

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