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In Season One, Tyler and Jeremy were enemies, while Tyler and Matt were still best friends. It wasn't until Season Three that Jeremy finally became close friends with both Matt and Tyler, and it wasn't until Season Four and Season Five that the relationship between the three young men formed a close unit. Matt, Jeremy, and Tyler all used to live in the Lockwood Mansion in Mystic Falls, before Tyler and Jeremy left Mystic Falls in Season Six finale.
Throughout The Vampire Diaries SeriesPilot, Jeremy, Matt and Tyler were all seen in the Mystic Grill, when Jeremy tried to talk to Matt's sister, Vicki, but she shot him down and insisted she was working. Tyler and Matt were eating at a nearby table, and Tyler openly flirted with Vicki, much to Matt's displeasure-- he even went so far as to call Tyler a dick for hooking up with his sister. Additionally, Tyler and Jeremy both watched Matt when he introduced himself to Stefan Salvatore, who had just arrived to the restaurant with Elena, Matt's ex-girlfriend and Jeremy's sister.
Later in the episode, after Tyler forced himself on Vicki during the back to school party, Jeremy and Tyler argued again, and nearly got into a fight until Jeremy stopped at the last moment. Later, shortly after Vicki was bitten by a vampire, Jeremy found her in the woods and carried her back to the party, where Matt and Tyler helped call for an ambulance. Matt later accompanied his sister to the hospital in the back of the squad.
In The Night of the Comet, Jeremy lost track of Vicki and went over to the table where Elena, Tyler, Matt, Caroline, and Bonnie were sitting to ask them if they had seen her. Jealous that Jeremy was spending time with Vicki instead of him, Tyler insulted Jeremy by replying, "You're her stalker. You tell us." He then remarked that she probably found some other "pill-pusher" to replace him, knowing that the drug accusation would get Jeremy in trouble with Elena and his guardian Jenna. Jeremy became angry and retorted that he and Vicki had slept together on more than one occasion, and added that he didn't even have to force her into it like Tyler had with Vicki the night before. Tyler called him a punk and tried to deflect, but Matt, who was furious to hear this news, decided to focus on all of them finding Vicki and making sure that she was safe.
In Friday Night Bites, Matt made a comment to Jeremy about Vicki making her boyfriends work for it when Jeremy sees Tyler and Vicki flirting nearby. Jeremy replied that he found Vicki pretty easy to understand, just as Tyler walked over to join them. Jeremy and Tyler got into another argument after Tyler remarked that he had no need to impress Vicki because, in his words, he had "already won," which caused Jeremy to shove Tyler backward. Tyler threatened to hurt Jeremy even worse, but when Jeremy insisted that Tyler was all talk and no action, Matt stepped in at the last moment to prevent the fight from escalating further. Matt then lost his temper with his sister, as he believed she was the reason for Jeremy and Tyler's conflict in the first place.
Toward the end of the episode, Jeremy and Tyler fought again, even after Vicki to Tyler not to do it. Stefan tried to break it up, but Tyler punched him. When the force of the punch had little to no effect on Stefan, Tyler became suspicious, but was distracted when Jeremy smashed a liquor bottle and lunged toward Tyler. However, Jeremy hit Stefan instead, and the fight was broken up moments later when Elena arrived and intervened, resulting in the three splitting up. Later on, before the game, Tyler approached Matt in the locker room to talk to him, but Matt had no interest in talking and called Tyler a bully for always starting fights with people, including Jeremy. When Matt accidentally referred to Elena as his girlfriend, Tyler reminded him that Elena "dumped his ass." They then went to prepare for the game, which is when they both discovered Coach Tanner's body in the parking lot.
- Jeremy became roommates with Tyler and Matt.
- In Season One, Tyler bullied Jeremy and they fought over Matt's sister.
- All were very close to Vicki, Tyler and Jeremy both dated her and Matt was her brother.
- Matt dated Jeremy's sister, Elena.
- Both Tyler and Matt have dated Caroline Forbes.
- They are roommates, as of Season 5.
- They have interacted with all of the main characters.