Bonnie and Jeremy

The relationship between Bonnie Bennett and Jeremy Gilbert started mid-way through season 2 and finally culminated in their first kiss in episode fourteen, "Crying Wolf". Bonnie and Jeremy have known each their entire lives due to the fact that Bonnie is his sister's best friend. Bonnie cares very deeply for Jeremy and even tearfully told Emily Bennett, her ancestor, that she loved him when she was trying to bring him back to life.

Jeremy first developed feeling for Bonnie in season 2, episode 7, "Masquerade". Bonnie and Jeremy were setting up the plan to trap Katherine in a room at the masquerade party. Bonnie tells him that she doesn't enjoy being a witch because it never ends well for people like her (witches). Jeremy thinks it is very cool that she is a witch, and asks her why she helps when she doesn't like it. Bonnie tells him that she doesn't want anyone else getting hurt and that she doesn't know how to stay out of it. Jeremy, at that moment, develops feelings for Bonnie, admiring her courage and selflessness. Jeremy and Bonnie went to the Masquerade ball together where Damon and Stefan tried to kill Katherine, which failed when everything they did, harmed Elena. Jeremy was in on the plan for Bonnie to take on Klaus and fake her death when the other's weren't except for Damon. She later wakes to find Jeremy leaning over her. She hugs him gratefully and then immediately webcam chats with Elena.

In the episode before the season finale, she goes up agains Klaus for a second time after he kills Jenna. Before she leaves, Jeremy tries to stop her but is knocked out by a quick spell from her. He is devastated to learn of Jenna's death but probably relieved that his girlfriend was okay. She later stands by his side at her funeral. In the season finale, when Jeremy is shot accidentally by Sheriff Forbes, Bonnie takes him to the witch house so the witches could bring him back but they refuse, leading her to beg them for their mercy and proclaim her love for him.

They warn her that there will be consequences before bringing him back. She hugs him gratefully. But the consequences proved to be more than she knew and soon she was confronted with the revelation that Jeremy now had the ability to see ghosts, specifically the ghosts of his ex-girlfriends. When she goes away for the summerto be with her father and his family, she keeps in constant contact with Jeremy through emails and texting. When she finally does find out, she doesn't appear to be too bothered until she finds out that Jeremy had kissed Anna in her ghost form. Deeply hurt and troubled by the revelation, she breaks up with him at the end of "Ghost World". She later, sadly tells Elena that now she doesn't have a date to the homecoming dance.