|“||And now, I am a killer. And all I am going to do is kill more, and more, and it's all. Your. Fault!||”|
Stefan met Ivy some time after he left Mystic Falls and began a romantic relationship with her. Shortly after Caroline and Enzo found them, Enzo killed Ivy as revenge against Stefan leaving Caroline behind. Ivy was then turned into a vampire. Ivy began to resent Stefan for this due to her heightened emotions. Stefan and Ivy's sweet, romantic relationship soon turned sour as Stefan wanted nothing to do with Ivy anymore, especially finding her irritating after she was turned. Ivy also started to cause trouble around Whitmore College, which Caroline had to be responsible for taking care of Ivy. Unfortunately, Stefan and Ivy never rekindled their romance being Ivy was killed by Tripp Cooke after being sent through the Magic Purification Spell that surrounded Mystic Falls.
Throughout The Vampire Diaries Series
In the season premiere, Ivy stops by Stefan's work to pay him a visit. Later, they are seen in bed. She wants to know more about him as they having been seeing each other for two months. He tells her that he is a vampire and she becomes annoyed with him. However, he states that he cares very much about her which makes her happy.
In Yellow Ledbetter, Ivy wanted to cook a breakfast for Stefan. He interrupted her and they had a discussion about their relationship. Ivy thought Stefan wasn't as into her as she was into him. He suggested that he can cook a dinner for the two of them. Later in the episode Enzo and Caroline surprised Stefan and Ivy, when they unexpectedly appeared in his house. Stefan invited them for the dinner too. During the dinner, Enzo killed Ivy.
In Black Hole Sun, Stefan finds out that Enzo turned Ivy into a vampire.
In The World Has Turned and Left Me Here, Ivy blames Stefan for her becoming a vicious vampire. She rushes to attack him before having her neck snapped by Stefan. Stefan seeks the help of Caroline in dealing with Ivy's vampire cravings. At the end of the episode, Ivy is captured by Tripp and killed by entering Mystic Falls, across the anti-magic border.
In The More You Ignore Me, The Closer I Get, Caroline talks about Stefan and Ivy's relationship while walking in the woods.
- Ivy: "Now tell me something I don't know about you."
- Stefan: "I'm a vampire."
- Ivy: "You're so annoying.
- Stefan: "Hey. And I like you."
- She thought he was joking when he claimed to be a vampire.
- Stefan and Ivy dated for 2 months before she was killed by Enzo in Yellow Ledbetter.
- Stefan was upset over her death as a human.
- She blames Stefan for her becoming a vampire.
- Stefan leaves Ivy as Caroline's responsibility after she turns into a vampire.
- When Caroline mentions Ivy in The More You Ignore Me, The Closer I Get, Stefan seems to be irritated.