Jessica and Jason Hook Up (Season 4, Episode 9)
It was a turning point for both characters when Jason and Jessica finally hooked up in the back of his truck after weeks of sexual tension: Jason had, to this point, been known for his good heart and penchant for attachment-free sex. His attempts to turn his relationship with Crystal into something more led to his being kidnapped, forcibly made a part of a mating ritual and possibly turned into a were panther (though his worries were abated when he didn't shift at the next full moon), so he didn't exactly have the best romantic track record. But now he's stuck in an even worse dilemma: it seems like Jason is, in fact, falling in love with his best friend's ex-girlfriend, who is also his sister's ex-boyfriend's vampire progeny. Meanwhile, Jessica, who was turned into a vampire at the age of 17 against her will (as Bill's penance for staking Fangtasia employee Longshadow), has been struggling with her now permanent-teen emotions and her newfound vampire hypersensitivity, and all she wants after ending her old-married-couple relationship with Hoyt is to have some fun. It's a match so wrong it's right – and one that undoubtedly will challenge both characters.