Usually, when Bonnie talks in her sleep, she murmurs names of friends and long-deceased relatives. One night, however, she murmurs Damon's instead - and for once, Damon can't lord it over her, because if he does, then he's already lost the game between them. (Spoilers for S6).
The night before he leaves for college, Jeremy fears he'll lose the friendship he has with Tyler - and instead, learns that he had absolutely nothing to worry about in the first place. (Spoilers for S5!)
Sometimes, Bonnie and Jeremy just needed to get away for the weekend and pretend for a moment - if only a moment - that they were normal. (Bonnie/Jeremy, slight spoilers for S5)
When Jeremy receives a letter from the Watchers' Council, he's not sure what to expect, but one thing's for certain: joining it sure beats sticking around Mystic Falls for another summer. Jeremy/Bonnie, implied Damon/Elena.
Stefan promised that he'd never chase his brother's ghost, but Jeremy makes a compelling argument - to summon Bonnie and Damon from beyond the Other Side - that Stefan can't quite ignore. (Spoilers for S5, Bamon)
Giving a lost high school student directions shouldn't have been this complicated. Bonnie expected to just help Scott McCall on his merry way, but when he accidentally ropes her into his crazy supernatural world, she realizes she might've found the perfect guy after all.
What if Damon was the judgey witch to Bonnie's (reformed) vampire? Damon may have promised Stefan a magic-free life, but after Bonnie Bennett rolls into town, he's not so sure he can keep it for much longer. (role-reversal AU; Defan & potential Bamon)
Raven can't pretend to know fatherhood, but after Karol does something incredibly stupid, he understands why so many his age know it so well. (Heavy canon spoilers, platonic Karol & Raven)
Stacey McGill finally gets the chance to babysit a member of Mystic Falls' Founding Families and learns that while the kid may be normal, the people surrounding him sure aren't - and some of them (like Damon Salvatore & Jeremy Gilbert) may become her true loves.
There's this theory that every few hundred years, two people consistently seek each other out, because only they can ease the other's heartaches. Elena doesn't believe in the supernatural, but even she knows she can't fight her destiny. (AU; spoilers for s5!)
Five people from Mystic Falls that Klaus drunk-dialed (and one he almost didn't).
Normally, Bonnie would've pushed Damon out of her way. Normally, she wouldn't have bothered acknowledging his presence. Normally, she wouldn't show any signs of weakness, but her newfound status as the Anchor kinda threw a wrench in that plan. (Bamon, implied Beremy, past Delena; spoilers for 5x15 and 5x16!)