When Chuck goes to see Blair, she tells him she can't watch him self-destruct any longer but Chuck leaves her house dejected. She tells him that she believes in him. The last shot is of him left bleeding in the alleyway. Chuck and In the season premiere, "Summer Kind of Wonderful", we learn Blair has stayed in Europe. Chuck begged Blair to stay with him, and to not end their relationship, saying "We have to see this through until the end", but Blair replies with "This is the end" and thus ultimately ending the relationship, causing him to go back to seducing any woman he desired, only to get over how devastated he is. Just afterwards, Serena realises that it wasn't Chuck who was sending the packages after all, but her ex-best friend Georgina Sparks.Serena spirals out of control after Georgina continues to blackmail her, and when she spends all night partying, Blair enlists the help of Chuck and Nate, despite the fact that they hate each other because of Chuck and Blair's affair. They do this in order to ensure that their relationship stays exciting. Jack says that there is another way to solve the situation, Marrige. That's why they want them to sign a "real treaty", with provisions for every possible interaction they could have. They share several drinks together, and he then challenges her to dance onstage, a dare that she accepts. Lily and Chuck have an argument and Raina yells at Chuck after hearing and seeing what he was doing to Lily, because loyalty to family is extremely important to her. He is described as having flamboyant sense, with a penchant for scarves. Lily reveals at the conclusion of the episode that Blair is awake and doing fine, but whether or not Chuck has survived was not revealed. He is mugged by two men. Chuck and Bart have a talk where Bart asks Chuck that he has to stop this childish nonsense, Chuck responds that Bart has taken everything from him and now is the time to take everything from Bart. They find the engagement ring that was supposed to be Blair's, but Chuck does not want to give it up, telling them he has money to give and that he is rich, but he has to keep the ring. Raina then goes on to say that she actually cares about her family, and that she wants to end their relationship.Chuck tries to win Raina back by sending Nate to convince her what a good guy he is, but Raina develops feelings for Nate instead, and they have a short lived relationship; this is awkward for Chuck at first, but he eventually gets over it.Chuck is finally back to wanting Blair, but he cant connect with her because Blair is ignoring him. From shop COBRACARDSS. In the following episodes Chuck returns to the Upper East Side with revenge for Lily. Because she stayed at the hospital with Dorota too long, she is late meeting Chuck and finds the peonies he had bought for her in the garbage can. After being hurt so much, Chuck is unable to admit his feelings and leaves Blair alone on the street. In the episode "The Lady Vanished", Chuck learns that the mystery woman's name is Elizabeth Fisher and she may be his mother. He admits that he paid the dowry, but for her freedom and her freedom only. Lazy and vain, Chuck's only interests are sex and money, and he is frequently chided by his father for lacking ambition and performing poorly in school. Louis insists that Blair will be there.Some time later, at the Van Der Woodsen apartment, Blair is preparing to spend the summer with Louis in Monaco, but is civil when she says goodbye to Chuck.