Damon Chose Bonnie Over Elena In the second season, Damon vowed that he would never choose anyone over Elena, and even used Bonnie as a person he'd be willing to sacrifice. One thing the series is especially talented at is relationship development, and Bonnie became the best friend that Damon had ever had.
Damon And Elena
No matter how viewers felt about Damon and Elena's relationship, Elena is Damon's only real love interest for the majority of the series.
Damon Chooses Bonnie Over Elena
When he's forced to decide whether to save Bonnie's life or let Elena fall into a Sleeping Beauty-type slumber, he picks Bonnie. In the past, Damon would have thrown Bonnie to the wolves, but he had grown to love and care for her in a way that neither of them thought was possible.
On The Vampire Diaries, Bonnie and Damon started as enemies but became best friends. In the novel series, they dated but not on the show. Here's why. Bonnie Bennett (Kat Graham) and Damon Salvatore (Ian Somerhalder) were never a couple in The Vampire Diaries, unlike in the series of novels created by L.J. Smith.
Though she and Damon would do nearly anything for each other and Damon is visibly jealous of her relationship with Enzo, the show refused to entertain the possibility that they could've been anything other than friends—and the quality of the series suffered for it.
Stefan Salvatore
Stefan loved Elena more than anyone else and was entirely devoted to her. They both wanted to pursue a human life, whereas Damon enjoyed being a vampire. Elena reunited with Damon in the series finale, but she would potentially have been a lot happier if she had chosen to be with Stefan instead.
After Damon had saved Bonnie's life, they shared their very first kiss (which was described as incredibly intense by Bonnie herself).
Enzo. Enzo is a Vampire who becomes Bonnie's new main love interest in the beginning of the seventh season. Her connection with him is the strongest out of all the relationships she has been shown to be in.
Bonnie instead ends up in a romantic relationship with Enzo toward the end of the show. The two never got to live their lives together since Enzo died. On the other hand, Bonnie got to live her life and eventually grow old. Fans who loved the couple have wondered if they will see each other again in the afterlife.
The episode ends with Elena and Damon fighting over their relationship and how much one depends on another. They decide to break up because their love makes them something else of what they really are but they end up in bed together because they cannot fight what they feel for each other.
It's easy to forget that Damon wasn't always desperately in love with Elena, and when they first met on the show, he was willing to let her die on more than one occasion. All he cared about was getting Katherine out of the tomb, but things changed when he realized Katherine had been free all along.
Bonnie The Teenage Witch (Bonnie)
When Damon chooses to save Bonnie over Elena, he claims that he's not out of nicknames for her quite yet. Although there are too many witch-related names to count, "Wicked Witch of the West" and "Witchy" are honorable mentions.
Off the dream, Damon takes a stake and stabs Rose in the heart killing her as a mercy to her pain, crying while he does it. Elena tries to comfort Damon who insists he does not care about Rose's death but he finally admits that he does not like to feel because it hurts.
Lexi, having grown fond of Damon, ended up having a night of wild sex with him. However, it turned out that Damon had lied about having feelings for her, and only pretended to in order to get her off his back regarding his bad behavior.
Elena and Bonnie were originally best friends, while Caroline was closer to Bonnie, mainly due to being jealous of Elena. After Caroline's transformation into a vampire, her friendship with Bonnie deteriorated for a short time, but Elena was there for her, strengthening their friendship.
Damon gradually fell in love with Elena throughout the first season of The Vampire Diaries. Although he comes to Mystic Falls to free Katherine from the tomb, Damon falls for his brother's girlfriend and is irrecoverably in love with her throughout the rest of the series.
There's also the fact that Caroline was a better vampire in general but that was mostly because she had to be. Unlike Elena she didn't get coddled, no such luxury was offered to her instead she had to do right or live under the threat that she might be killed again.
Damon is successful in relieving Bonnie of her Huntress side. Damon later calls Bonnie and she jokes with him, but all is forgiven between them.
But Season 6 changed everything. For the first time we saw Damon and Bonnie work together. They were each other's rocks in the Prison World. Then, upon their release, Damon was faced with an unimaginable decision: save Bonnie and lose Elena for the next 60 years or let Bonnie die and get the love of his life back.
Bonnie was stuck in the prison world and forgave him. Elena ends up in a relationship with him despite all he's done to her. Stefan chooses Damon over Elena despite Damon stealing his girl from him and killing his best friend.
The age difference between the two is too minor to make much of a difference. The more decisive element is that Elena has had some combat training from Alaric and Damon. Caroline is actually Stronger, but Elena was trained to kill vampires as a human.
DELENA: More Passion and Danger
While Stefan offered Elena a sense of safety and stability, Damon gave her danger and passion. He allowed Elena the freedom to explore who she was regardless of morality. He sparked a passion in her that let her get in touch with her inner bad girl.
Stefan encourages her recovery from the traumatic event and gives Elena a new appreciation for life. Elena later credits Stefan for helping her through her depressive period. Stefan ultimately did more good for Elena than Damon did by encouraging her happiness instead of causing her misery.