6 times Chuck Bass wanted to say I Love You.
Chuck Bass had never said "I love you" to anyone in his life. He did not believe in those words. How could he? When no one had ever said those words to him. In his childhood all he ever wanted was to be loved by his father. But all he got were cold stares and ignorance. That wouldn't have been the case if his mom hadn't died giving birth to him. Even though his dad or Mr. Bass never told him but he knew in the corner of his heart that he blamed him for her death and that is the reason he was never the dad Chuck had longed for his entire life. He was just his father, never his dad. Everyone thought of Chuck as the notorious playboy of Upper East Side which was true as he himself created that image for himself but there were times when all he wanted was for someone to care. For someone to be his crying shoulder, to hold him tight in their arms and tell him that everything was going to be ok. But he never got that. He was cold-hearted just like his dad. But then his life changed when he fell in love with Blair Cornelia Waldorf. He eventually told her he loved her even though it took him an eternity and their relationship was amazing while it lasted. She was the family he never had. But he did what he does best and screwed it all up not once, but twice and lost her forever in the process.
There were 5 times when he wanted to tell someone he loved them but he chose not to because well he was Chuck Bass but there was one time he wanted to say those three words and eight letters to someone so badly but just couldn't.
The first time Chuck Bass wanted to say I love you was to Serena Van Der Woodsen. He was 5 when he first met her in the school playground. He was all by himself when she came running towards him asking him if he wanted to play. He wanted to say no but when he saw her smiling that amazing smile of hers at him he couldn't refuse. And that's when he became friends with Serena, Blair and Nate. They were the non-judging breakfast club. It took Nate and Blair a while to like chuck. Chuck always felt like an outsider but it was Serena who always got him involved in everything. He remembers the day she left without saying goodbye to anyone but him. She had called him at one in the morning and told him she wasn't coming back. He wanted to stop her but just couldn't say it out loud. But the day she returned, as much as he hates to admit it, he was extremely happy and just wanted to tell her he missed her so much and that he loved her (as a sister) but he chose not to. Why? Because he was Chuck Bass.
The second time Chuck Bass wanted to say I love you was to Nathaniel Archibald. Chuck only cared about three things in his life Money, the pleasures money brings, and Nathaniel. He was always there for him no matter what like the time he saved him from that jackass, Carter Baizen. He hated that time when Nathaniel found out about him and Blair. He tried so hard to apologise but Nathaniel didn't listen. They finally patched up but again their friendship hit the rocks when he became friendlier with Dan. Chuck wasn't the jealous types but he really wanted to kill Dan that time. When he got the call from Vanessa regarding Nathaniel's father it scared him because he thought he was going to lose his best friend. He wanted to tell Nathaniel not to go, to tell him that he loved him (as a friend) but chose not to. Why? Because he was Chuck Bass. And Nathaniel never left so thank the lord.
The third time Chuck Bass wanted to say I love you was to Blair Waldorf. He was always fascinated by his best friend's girlfriend and was awestruck by her beauty but he never thought of her in that way. That all changed that night when he saw her dancing in Victrola. Blair had finally let go of her make-believe image and just be herself. Soon enough he fell in love with her but never had the guts to ever say that out loud. During his father's funeral she had finally told him that she was in love with him. This was the first time someone had said that to him. He wanted to tell her that he was madly in love with her too and he has never felt this way about anyone but he chose not to. Why? Because he was Chuck Bass. So he just left her there all alone
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The forth time Chuck Bass wanted to say I love you was to Eric Van Der Woodsen. Eric had been the brother Chuck never had. They had a very special bond and as much as Chuck would never admit it he truly cared about Eric's well being and was certain that Eric knew it too. Eric cared about him too. It was evident when he tried to stop him from leaving during his father's funeral and told him that he, Serena and lily were his family. But Chuck being Chuck told him that they were not related and did not give a crap about family. During his party at Victrola when he met him again he wanted to tell him that he misses him and loves him (as a brother) but chose not to. Why? Because he was Chuck Bass.
The fifth time Chuck Bass wanted to say I love you was to Lily Van Der Woodsen. His father had various women in his life but there was only one person he ever liked and that was Lily. She was like the mother he never had. But he never told her that. He instead blamed her for his father's death even though he knew it wasn't her fault at all. But then he became close to her when she welcomed him back to her family. When Chuck found out about Lily having cancer he was terrified and didn't even go to see her. It's not that he didn't want to. He did but was too scared because he thought he was going to lose her. He finally did speak to her and told her that everything was going to be ok. He wanted to tell her that he loved her (in a mother kind of way) but chose not to. Why? Because he was Chuck Bass.
The sixth time Chuck Bass wanted to say I love you was to Blair Waldorf. He had messed up with her big time. He had literally sold her out for what? His stupid hotel and to whom? His uncle Jack Bass. She had finally given him a second chance but what did he do. He slept with Jenny Humphrey. Even he couldn't forgive himself. When he was lying in the streets of Prague bleeding after being mugged and shot, all he could think about was her. All he wanted to do was tell her he was sorry for all the hurt that he caused her and that he was never going to love anyone the way he loved her and she was the most important person in his life. But he couldn't say it even when he wanted to so badly. And it didn't even matter that he was Chuck Bass because he wasn't Chuck Bass without Blair Waldorf
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