What Major Relationships Did Jeremy Gilbert Have On The Show?

I still get a little misty thinking about Jeremy in 'The Vampire Diaries'—his relationships are the heartache-and-healing arc that made him feel real to me.

He had a huge, defining bond with his sister Elena that was protective and fragile at the same time; so many scenes are built around that sibling love and the way grief pushes them together. Romantic-wise, the big ones people remember are Vicki Donovan (an early, messy flame that ends tragically) and Anna (a gentler, complicated connection that ties into the show’s ghost/vampire lore). Both romances were less about teenage drama and more about Jeremy trying to process loss and who he was becoming.

Beyond romance, Jeremy leaned on a circle of mentors and friends: Alaric stepped into a guardian/mentor role, Matt was the down-to-earth buddy who kept him anchored, and the Salvatore brothers were guardian-ish figures in their own rough way. He also had a rocky, sometimes painful relationship with his parents and family secrets that shaped his trust issues. Those layers—the family, the short-lived loves, the friends and mentors—made his growth on the show feel honest to me, like watching someone stumble toward adulthood while the supernatural did its worst.

Some fans focus on the romance, but I always find Jeremy’s mentor and friendship ties just as interesting. Early losses pushed him into relationships that were as much about coping as they were about romance: Vicki was raw and dangerous, Anna was tender and tragic. Those two shaped his emotional blueprint. Flip that around and you see Alaric filling an adult-shaped hole—someone who both disciplined and defended him—while Matt offered everyday loyalty, the kind of friendship that doesn’t need supernatural explanation.

There’s also the way the Salvatores hovered around him: Damon and Stefan both acted as smoky, imperfect protectors, each in their own style, which complicated Jeremy’s idea of who to trust. Add in the betrayals and revelations from his parents and extended family, and you’ve got a young man whose romantic choices were inseparable from his need for stability. For me, his relationships are less a list of dates and more a map of how he learned to cope, fight, and finally stand on his own two feet in the middle of the chaos.

I tend to think of Jeremy’s relationships as three categories: family, romantic, and mentor/friend. Family comes first: his bond with Elena is central—she’s his anchor through grief after the early tragedies. On the romantic front he had the volatile Vicki Donovan and then a deeper, bittersweet relationship with Anna, both of which pushed him into the supernatural side of the world emotionally. As for mentors and friends, Alaric acted as a protective older figure after Jenna died, while Matt stayed loyal in a normal-kid way that grounded Jeremy. The Salvatore brothers also played a role, alternating between protectors and complications. Jeremy’s interactions with his father and with town secrets added layers of mistrust and trauma that shaped his choices. When you rewatch 'The Vampire Diaries', Jeremy’s interactions read like a teenager trying on roles—lover, brother, student, and sometimes soldier—against a backdrop that kept testing him, and that made his moments of growth feel earned.

When I think about Jeremy in 'The Vampire Diaries', I see a kid shaped by people more than plot points. His closest relationship is with Elena—pure sibling loyalty. Romantic highlights were Vicki, whose tragedy hit him hard, and Anna, whose storyline was haunting and formative. Alaric became a father-figure who offered structure after Jenna’s death, while Matt remained the steady, normal friend. The Salvatores acted as rough-around-the-edges guardians, and family secrets (including his father’s return) added mistrust that affected every bond he formed. Those connections—family, lovers, mentors, friends—are what turned Jeremy from a reactive teenager into someone who actually mattered in the larger story, and that’s what hooks me every time I watch.