When Clare and Jake were children, Jake wasn't the nicest to her. Clare initially started off disliking him as he had a habit of throwing dead frogs at her. Jake offered Clare a way to move on, after she was upset with Eli in LoveGame, by kissing her. Clare seems to begin liking him, as she discusses the kiss with Alli later in the episode. Despite having feelings for Jake, Clare tries to hide them, worried about getting into another relationship. Things change, however, when Jake provides a way for them to have a relationship, without all the pain and hurt - being Friends With Benefits. Both decide to become official, after their feelings become to much to just be casual, although they hit a snag as their parents announce they are also dating.
Clare and Jake continued dating in secret, with just a few small problems, but it all changes when Glen and Helen announce they are getting married. Glen already told Jake so he knew it. Jake congratulates them, while Clare is upset. Jake ends up breaking up with Clare at prom, wanting his dad to be happy. After seeing Clare again at his father's wedding, Jake confesses he still loves Clare, although she wants nothing to do with him after he hurt her. Only when she realizes she does, she catches him locking lips with Alli. Jake tells Clare, Alli kisses him, which leads Clare to cutting off ties with Alli and begin dating Jake again.
After reuniting, believes she is ready to have sex with Jake, but after realizing her can't give her the forever she wants, Jake blows her off and leaves. Clare realizes they don't have a future together, with their parent's married, and breaks it off. When Jake starts hanging out with Jenna more Clare decides to move out. She ends up living with a girl named Summer. Jake gets worried and starts questioning her new home. Later it's revealed that Summer was a drug dealer and Jake goes after Clare before the police come and arrest Summer. Once they get home they decide being siblings could be great for the both of them. Throughout the end of season 11 they seem to be fine and are on good terms again. While Clare is dealing with the aftermath of Asher assaulting her, Jake is seen comforting and trying to help Clare as best as he can, even by beating up the hockey team since they were bugging Clare.
Clare and Jake continued dating in secret, with just a few small problems, but it all changes when Glen and Helen announce they are getting married. Glen already told Jake so he knew it. Jake congratulates them, while Clare is upset. Jake ends up breaking up with Clare at prom, wanting his dad to be happy. After seeing Clare again at his father's wedding, Jake confesses he still loves Clare, although she wants nothing to do with him after he hurt her. Only when she realizes she does, she catches him locking lips with Alli. Jake tells Clare, Alli kisses him, which leads Clare to cutting off ties with Alli and begin dating Jake again.
After reuniting, believes she is ready to have sex with Jake, but after realizing her can't give her the forever she wants, Jake blows her off and leaves. Clare realizes they don't have a future together, with their parent's married, and breaks it off. When Jake starts hanging out with Jenna more Clare decides to move out. She ends up living with a girl named Summer. Jake gets worried and starts questioning her new home. Later it's revealed that Summer was a drug dealer and Jake goes after Clare before the police come and arrest Summer. Once they get home they decide being siblings could be great for the both of them. Throughout the end of season 11 they seem to be fine and are on good terms again. While Clare is dealing with the aftermath of Asher assaulting her, Jake is seen comforting and trying to help Clare as best as he can, even by beating up the hockey team since they were bugging Clare.