Elena Gilbert had a ionate and all-consuming romance with Damon Salvatore in The Vampire Diaries. Damon initially arrives in Mystic Falls as Elena's boyfriend Stefan's older, antagonistic brother. Elena gradually falls in love with Damon and the two finally reunite in the series finale "I Was Feeling Epic."
Damon and Elena's romance was ionate but problematic. The older Salvatore committed countless awful acts that hurt Elena and her loved ones. Elena may have loved Damon but, looking back, perhaps she should have been with someone else instead...
Elijah Mikaelson
Elijah and Elena shared significant chemistry in all of their scenes together throughout The Vampire Diaries. The Original, who was in love with previous Petrova doppelgangers Tatia and Katherine, holds Elena in high regard and has a great deal of respect for her. He tells her that her comion is a gift and warns her to hold onto it.
Elena trusted Elijah despite the warnings of both Salvatore brothers. She also had a lot of respect for Elijah even after he failed to kill Klaus during the ritual in Season 2.
Matt Donovan
Matt Donovan is Elena's first love and one of her best friends. The two dated during high school before the events of the series. Elena was a popular cheerleader and Matt was a football player, and both teens were adored by the town.
Elena breaks up with Matt before Season 1 following the deaths of her parents. He remains one of her best friends though and sticks by her side throughout the series. Matt continues to harbor a soft spot for Elena and, in hindsight, she may have been happier staying with him.
Bonnie Bennett
Bonnie Bennett is Elena's best friend and the pair have been friends since childhood. Both girls grew up in Mystic Falls and Elena is the first person Bonnie tells about her recently discovered witch powers in Season 1. Bonnie uses her magic to save Elena countless times and sacrifices her life for hers.
Bonnie loved Elena and consistently gave everything to protect her. Elena may have been happier ditching Damon for her best friend, who knows and loves her arguably more than anyone else.
Liam Davis
Damon and Elena are torn apart after the Other Side is destroyed. Damon and Bonnie become trapped in the 1994 prison world and a devastated Elena struggles to cope without him. She asks Alaric to compel her to forgot Damon and begins to move on with her life.
Elena dates Liam briefly and she seems happy until she has to erase Liam's memories of their relationship. This highlights that Elena, for a while, was happier without Damon and would have potentially been better off if they had remained apart.
Tom Avery
The Mystic Falls gang learns about the true origins of the doppelgangers in Season 4. Qetsiyah tells Damon that doppelgangers of Silas and Amara are destined to be soulmates. Fans meet Stefan's human lookalike Tom Avery who, if Qetsiyah is correct, was fated to be with Elena.
Tom was a good person who was kind, brave, and comionate. Human Elena would have ired Tom greatly. They shared several qualities that she does not have in common with Damon.
Caroline Forbes
Caroline Forbes is Elena's other best friend and an integral member of the Mystic Falls gang. She is initially a frenemy of Elena's in Season 1 but matures greatly after Katherine turns her into a vampire. Caroline, like Bonnie, stands by Elena and risks her life to keep her friend safe.
Caroline and Elena remain friends throughout the series, despite coming to blows without their humanity. Elena tries to protect Caroline from Damon early in Season 1 and may have been better off sticking with her friend against the older Salvatore.
Finn Mikaelson
Elena has a tumultuous relationship with the Mikaelson family. Klaus almost killed her during the ritual sacrifice in Season 2 and attempts to kill her several times afterward. Kol targeted the Gilberts in Season 4 and Rebekah caused Elena's death and transition into a vampire.
Elena shared few scenes with Finn but the eldest Mikaelson sibling, like Elijah, could have made a great match for the Petrova doppelganger. Finn detested vampirism and would have at least encouraged Elena to live a normal, human life.
Rose
Rose initially kidnaps Elena in Season 1 and attempts to use her as a bargaining chip with Elijah. The vampire then heads to Mystic Falls and shares a brief romance with Damon. She bonds with Elena as she nurses her through a werewolf bite and appears genuinely fond of the doppelganger.
Elena tries to help Rose after she is bitten by Jules, despite being attacked by the dying vampire. It would have been interesting to see both women ditch Damon and pursue adventures of their own.
Lexi Branson
Elena was initially wary of Lexi until discovering that she was Stefan Salvatore's best friend. She becomes friends with Lexi until the vampire is staked to death by Damon. Lexi reappears as a ghost sporadically in the series and teaches Elena how to make Stefan turn his humanity back on.
Elena and Lexi bonded over Stefan and could have remained friends after their break-up if Lexi had lived. Lexi was similar to Elena in many ways, but also had a wild side and would have encouraged Elena to have more fun.
Stefan Salvatore
Stefan and Elena's romance was epic. They meet in the pilot episode of The Vampire Diaries and are in a relationship until Season 4. Stelena fans were dismayed when Elena ended up with Damon and many still believe that the doppelganger chose the wrong 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.