Granted, the Salvatores have both been alive for over a hundred years. We suppose it was bound to happen? Regardless, it certainly must make it awkward for them to talk about their love lives, considering how intertwined they are. Let’s take a look back at the ladies they’ve both loved.
The one who started it all. Katherine (Nina Dobrev) was playing with both brothers’ hearts and bodies. “You have no idea of the future I have planned for us, Stefan. You, me, and Damon,” teased the vampire in 1864. Both brothers fell madly, but while Damon drank the she-vamp’s blood willingly, Stefan had to be compelled. Yet she never compelled his love. “It was real and so was mine,” Kat tells the younger Salvatore more than a century later. And when Damon asked the doppelganger for the truth about how she felt, she told him, “I’ve never loved you. It was always Stefan.” Over 140 years, and she still had the power to shake them both.
Is it hard for vampires to find each other in a city? Something drew Rebekah (Claire Holt) and Stefan together in 1920s Chicago — perhaps the scent of human blood? “Careful, Mr. Salvatore,” she purred at him. “You’re still wearing your date.” The two later shared a meal (aka a brunette flapper) and a penchant for sadistic games. Bex chose Stefan over her brother, so Klaus (Joseph Morgan) killed her and wiped the younger Salvatore’s memory of them both. When she was resurrected nearly 100 years later, Stefan showed little interest but Damon had no trouble bedding the blond after someone else hurt his feelings. The two got physical again when Damon wanted to get some info. Now it it's Stefan’s turn once again.
Elena It must have been like a dream for both Salvatores: A nicer, less twisted, equally gorgeous version of the woman they both loved. Katherine’s doppelganger, Elena (Nina Dobrev), met both brothers on the same night, but she didn’t remember either of them. Damon compelled her to forget him, saying that she wanted “a love that consumes” her. Stefan saved her life that night and then properly introduced himself months later. At first, Elena only had eyes (and between-the-sheets time) for Stefan, though a friendship grew between her and Damon. The two became even closer when Stef went Ripper. Turning into a vampire changed Elena’s feelings for both brothers, and — sire bond or no — convinced her she loved and wanted to be with (and sleep with) Damon.
So there you have it. The brothers’ venn diagram of ladies overlaps quite a bit. And who knows what happened in those lost decades. Maybe they’ve each shared a moment with Lexi (Arielle Kebbel) or perhaps Stefan knew Sage better than we realized.