All of the main characters have come a long way from who they were in The Vampire Diaries Season 1, but Damon Salvatore is the most unrecognizable. When Damon returns to Mystic Falls in the pilot episode, he has two goals: free Katherine from the tomb, and follow through on his promise to give Stefan an eternity of misery.
Falling in love with Elena causes everything to change, and Damon reveals that he's not at all who others perceive him to be. Damon might try to hide his true self, but it only takes a few seasons for everything to come to light. Knowing what viewers do now, there are several things about the future that Damon's past self would look forward to.
Damon Finds Peace
Damon leaves the optimism to Caroline and always looks at the negative side of things. Nothing in Damon's life ever works out the way he wants it to, which causes him to stop getting his hopes up and expect disappointment.
It's unlikely that Season 1 Damon would even believe in the possibility of finding peace—let alone that he'd achieve it himself. The promise that there is life after death and eternal happiness to be claimed, is undoubtedly something Damon's past self would be in awe of.
Damon Is Best Friends With Bonnie
Damon and Bonnie becoming one of the most important people in each other's lives is a twist that no one sees coming. It can be argued that Damon replaces Elena as Bonnie's best friend in The Vampire Diaries, as the two grow closer than Bonnie and Elena are ever portrayed to be.
While he isn't Bonnie's biggest fan during the first season, Damon respects her power as a Bennett witch. He attempts to use it to his advantage, but Bonnie is more inclined to kill Damon than help him. Damon would be happy to know that he befriended such a powerful being and managed to win Bonnie's affection.
Damon Becomes Human
Going only off of what viewers knew during the first season, being human is the last thing that Damon would be proud of. Yet, Damon reveals in The Vampire Diaries Season 2 that he misses being human more than anything in the world.
His stance on the matter tends to go back and forth throughout the series, but he always comes to the same conclusion. While there are plenty of risks that come with it, Damon's idea of a perfect life can only be achieved by giving up his immortality. By choosing to become a human, Damon gets back what's stolen when Stefan forces him to make the transition.
Damon Is Over Katherine
Damon spends a century and a half searching for a way to free Katherine from the tomb, only to discover she was never there in the first place. To make matters worse, he comes to the stark realization that he dedicated his immortal life to a woman who wants nothing to do with him.
Stefan is Katherine's priority in The Vampire Diaries, and while she claims to love Damon at one point, it's overshadowed by her feelings for his brother. No matter how angry Damon is during the first season, it's clear that he doesn't hate Katherine as much as he wants to. Moving on is never easy, but it's safe to say that Damon is one hundred percent over her by the time the series finale rolls around.
Damon Mends His Relationship With Stefan
Neither of the Salvatores is innocent in regards to the bad blood between them in The Vampire Diaries. Stefan forces Damon to become a vampire against his wishes, and Damon retaliates with violence. But no matter how many times Damon promises to give Stefan an "eternity of misery" it's the last thing he wants.
The brothers' bond is the very basis the show is built upon, and while Damon's pride might make it hard to admit, he loves Stefan more than anyone. Stefan is his family, and it would be a relief for Damon to find out they make amends.
Damon Finds Someone Who Returns His Love In Equal Measure
Damon's devil-may-care attitude never fools anyone, and Elena recognizes almost immediately that all of his actions have been in the name of love. He loves more powerfully than anyone in the series, which is why it sometimes seems like no one is equipped to match his level of devotion.
When The Vampire Diaries Season 1 is airing, it's hard to imagine anyone—let alone Elena—returning his love in equal measure. Damon is a hopeless romantic at heart, and to discover that he's going to love someone who loves him just as much back, would come as a shock to his past self.
Damon Marries Elena
Turning enemies into lovers is The Vampire Diaries' specialty, and Damon and Elena have the most well-developed romance in the series. As much as he wants it, Damon can't even fathom earning Elena's love during the first season.
She's head-over-heels for his brother, and even their friendship is often on the rocks. Yet, Damon and Elena's evolution becomes a main plot point, and the two live out a long and happy life together before walking hand-in-hand into the afterlife.
Damon Is Happy
Damon spends the entirety of The Vampire Diaries Season 1 acting as if he's invincible. However, his line, "I don't get hurt," tells viewers the complete opposite. Despite how hard he tries to hide it, it's clear that Damon is living out his own eternity of misery.
He feels unwanted, unloved, and undeserving of true happiness. If Damon was aware of the bright future waiting for him, his entire outlook on life would change. Damon's bad behavior is a result of having nothing left to lose, and he should know that he's not the lost cause he always believed himself to be.