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Throughout the beginning of the series, Elena and Stefan were always there for each other and Stefan always valued and respected Elena's choices and decisions when facing a new threat or enemy. Elena did not believe that Alaric was the killer and tried to defend him.

In the fifth season, their relationship remains strong as they had the perfect summer and Elena begins to start collage. Since Elena now has the freedom to accessorize, she dips into her jewelry box more often. Elena immediately regrets her actions, but Damon refuses her excuses, leading him to lash out at Kol and sleep with Rebekah, my hookup gets jealous causing Elena to become jealous and further straining their relationship.

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Elena ended their relationship shortly after the death of her parents Miranda and Grayson Gilbert. In the second season premiere, Damon struggles to understand and accept his feelings for Elena, while being toyed by the return of his former love, Katherine Pierce. At first glance, Elena and Katherine are identical yet their personalities, mannerisms, style, and makeup differ greatly and are generally aspects which give away their identity.

Elena is proud of Damon and encourages him to live his life while she is asleep. However, while rescuing Damon from Tripp, a newly surfaced Vampire hunter, Alaric crossed the town boarder of Mystic Falls. Since ending their romance, Elena and Stefan's relationship remained strained for some time as Stefan was still deeply in love with her. Elena and Damon share their first real official kiss. Thus Elena decided to renew their relationship, but she wanted to start over.

However, much to the shock and astonishment of everyone, Damon had returned to life. She and Katherine are similar in their abilities to manipulate others, and to think several steps ahead of Stefan or Damon, who are trying to save her. Throughout his time trapped, Damon missed Elena and held a strong desire to escape and be with her again. The letter reveals the truth regarding her love for Damon, but also encourages Elena to try and continue to live her life without him as the loss was too great. Elena physically resembles the original Petrova, Amara.

Elena is willing to sacrifice herself to make sure her family and friends remain unharmed, upsetting Stefan as he wants a future with Elena. Before The Other Side was completely destroyed, Damon said goodbye to Elena, declaring his love and revealing she is the greatest thing that has ever happened in his life. While knowing he is making the right choice, but still heartbroken, Damon reveals to Elena he will wait for her to awaken and won't sacrifice Bonnie. Elena ultimately decided to compelle her memories and love of Damon away with the help of Alaric.

Elena and Stefan's relationship is restored, but they begin to face new issues when Elena later learns about Stefan's bloodlust problem, resulting in him attacking an innocent girl. Elena speaks the truth all the time and it's brutal and not fun for the people who have to listen to it. She doesn't care about the rules. Elena is highly against his decision, wanting a future together. Elena was shock, confused and conflicted, but decided not to reverse the compulsion and chose to have Alaric keep the mementos if ever she changed her mind.

Refusing to give up and lose the love of his life, Damon didn't lose hope and tried to help Elena to jog her lost memories of their past together, but to no avail. In return, Elena finally begins to confess her feelings.

Eventually in the season finale, Elena truly confesses her feelings, admitting she is really in love with Damon, having fall out of love with Stefan. Due to this, Elena was afraid Damon would be miserable as a human and tried to convince him along with Stefan to change his mind.

Reluctantly, Stefan comes to realize the real deep meaningful and true love that Damon has for Elena, but still holds a glimmer of hope that he and Elena might get back together. Elena favors wearing dark blue jeans with t-shirts of various colors and Converse sneakers. The two bond over their fondness of Damon. Throughout the season, Elena and Damon grow more closer and they both make each other better.

Damon's selfless act shows he loves Elena so much he is willing to let her go to and live her life and once again declares his love for her before leaving. Once Elena finds Damon and returns to the Salvatore Boarding House, Elena remains by Damon's side, trying to make his last moments as comfortable as possible. Elena reveals although she still cares for Stefan, she no longer has the same feelings she once had, officially ending their relationship for good, leaving Stefan heartbroken.

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Upon the discovery, Elena confronts Alaric and he gives her several of the mementos from her and Damon's relationship, including a letter written to herself before the complusion. However, much to Elena's shock, astonishment and anger, Damon refuses to take the Cure. However, Stefan becomes worried about his and Elena's relationship being seriously threatened when he discovers his older brother, Damon has also fallen in love with her.

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In the fourth season, Elena and Stefan face issues when Elena becomes a vampire. Damon is worried Elena's feelings might not be real after discovering the sirebond between them. They dated briefly and Elena made him forget the relationship Gallery. Damon noticed Elena, believing her to be Katherine, but quickly realised the truth. Gradually over time, Elena and Stefan slowly managed to reconcile as Stefan comes to accept the love between Elena and Damon and they developed a close friendship.

Damon reveals when The Other Side was destroyed, he and Bonnie were transported to a Prison World and were trapped for months. Damon and Elena grew to develop an understanding and bond together, first beginning when they took a road trip to Georgia and by the end Elena saved Damon from a vengeful vampire and witch. When Damon saves Elena from nearly killing herself from the Hunters Curse as well as Stefan realizing her love for Damon has become more stronger and serious than before, Stefan and Elena break up.

Eventually after years of seperation, Damon and Elena were at long last finally reunited in the series finale. Shortly after the break up, Elena and Damon can no longer contain their feelings and after sharing a romantic dance, they make love for the first time.