Out of all the characters in The Vampire Diaries, Stefan Salvatore had the most compelling love interests. A vast majority of the women in the show fell for him at one point or another, and Stefan had incredible chemistry with almost all of them. Because of the number of relationships he had, Stefan Salvatore's love interests were complex.
The audience had several options to choose from, and many found themselves split over who Stefan should be with at the end of the show. Stefan ultimately ended up marrying Caroline Forbes before he sacrificed himself to save Mystic Falls, but not everyone was sold on their romance. Because of how well-rounded Stefan's love interests were, it's understandable why fans preferred some over others.
Updated on July 19th, 2021 by Kevin Pantoja: At the heart of The Vampire Diaries were plenty of romantic pairings. Although the crowd loved Elena with both Stefan and Damon, among other couples, something about Stefan's relationships always stood out. It was clear that he loved with everything he had and cared deeply for the ladies in his life. Stefan Salvatore's love interests were possibly the best in the series.
Qetsiyah
Qetsiyah and Stefan didn't actually date, but there was some hardcore flirting between the two. Elena even got jealous when she found out who her ex was spending time with, and barged over to Qetsiyah's house to see if anything was happening between them.
Admittedly, Stefan was just trying to gain Qetsiyah's trust, and Qetsiyah enjoyed pushing Elena's buttons, so she's definitely the worst of Stefan's potential romances on The Vampire Diaries.
Ivy
During his time away from Mystic Falls, Stefan fell for Ivy. She was more than a simple fling to him, and because she wasn't aware of all the supernatural creatures wandering around the world, Ivy was a person Stefan could go to escape what was happening around him. Her time was short in season 6 but she was a welcome addition.
That made her somewhat ideal for him. Unfortunately, she was turned into a vampire by Enzo, who used her to get his revenge on Stefan. Stefan tried to help her through the transition, but she was killed by Tripp after he kidnapped her and drove over the town line. While they were solid together, she wasn't one of Stefan's epic loves on Vampire Diaries.
Valerie Tulle
Originally unbeknownst to Stefan, Valerie was once pregnant with his child before she was attacked by Julian and had a miscarriage. Valerie never stopped loving Stefan and stayed by his side when he was on the run from Rayna Cruz. She was constantly putting her life on the line for him, and never asked for anything in return.
Of Stefan Salvatore's love interests, Valerie wasn't bad, so it's disheartening that she was only created as an obstacle for Stefan and Caroline. Valerie deserved better, as she was devoted to Stefan in a way he never was to her.
Lexi Branson
Many questions arose about the nature of Stefan and Lexi's relationship in The Vampire Diaries because of how close they were. However, they always denied that anything happened between them and insisted they were just friends. Audiences never got to truly know since their history was all before the series actually began.
There wasn't any romantic chemistry between them, so it was easy to believe that Stefan and Lexi were strictly platonic. But because of how well they got along with each other, many fans felt like they were a missed opportunity. Stefan always said that Caroline reminded him of Lexi, and after Lexi dies, Caroline is who he ends up falling for.
Rebekah Mikaelson
Rebekah Mikaelson wasn't easy to like at first, and most of the characters in The Vampire Diaries enjoyed pushing her buttons. But Stefan came to understand that she was just a girl who was dealt a bad hand in life. They had a pretty serious relationship decades earlier during the 1920s but Klaus erased Stefan's memories and forced Stefan to forget them both.
Although they never get back together officially, Stefan treats Rebekah the best out of everyone and he has a soft spot for her. They even had another sexual fling while working together in season 4. There were always sparks flying between them, so it's a shame their romance couldn't have gone on for longer.
Caroline Forbes
Caroline Forbes had a crush on Stefan ever since the pilot, and although they both dated other people, it was obvious that she never stopped liking him. She never pursued it knowing Elena's history with him and she went on to date Matt, Tyler, and even have a fling with Klaus. Stefan and Caroline grow close throughout the series and eventually become best friends.
Stefan was also hesitant to pursue a relationship with Caroline because he was convinced he didn't have romantic feelings for her. Many fans say it felt forced when they got together, as the romantic chemistry simply wasn't there. However, their story was well-written, and it made her one of the better Stefan Salvatore love interests.
Katherine Pierce
Even when Stefan was with Elena, The Vampire Diaries always teased the relationship between him and Katherine. Katherine was originally portrayed as heartless, but the show used her feelings for Stefan as a way to showcase her humanity. In the hundreds of years Katherine had been alive, Stefan remained the person she loved the most and possibly the only person she actually had real feelings for.
After Stefan's breakup with Elena, it only seemed natural that the show would give them another shot. Katherine's selfish nature prevented Stefan from falling back in love with her, but they were great together and it feels like a missed opportunity for character development. Stefan was one of the only people to show Katherine sympathy as she was dying and she helped him get past his fears after Silas locked him away underwater for months.
Elena Gilbert
Caroline once called Stefan "Elena's epic love." Stefan may not have been the love of Elena's life, as she ended up falling for his brother, but Elena was always the love of his. There was no one, before or after her, that Stefan loved the way he loved Elena.
It was often difficult to see him with other characters because of how ingenuine his feelings felt in comparison to those he had for Elena. Stefan was an entirely different person with Elena by his side, and after they broke up, Stefan was never the same. It's arguable that this romance remained The Vampire Diaries' greatest.