A/N: I am so on an inspiration roll this week. I finished Play It By Heart only yesterday and now I grace you with yet another one-shot. I know. It shocks me too. This was presented as a challenge by CB Fantasy on GossipGirlInsider to reveal a softer side to Jack Bass, so this is what I came up with. Please R&R!

Beneath The Surface

Jack slipped by Dorota unnoticed and made his way quietly up the stairs. He was planning to catch Blair by surprise. He had almost been successful in seducing her that night, but this time he was more determined to succeed. His nephew and that bitch had sent him off without a hint of hesitation and he knew this was his opportunity for revenge. He regretted his attempt to rape the woman, but he had acted on impulse. After all, it was a trait that the Bass men seemed to have running through their veins.

Now, he would take the most important thing from his life as Chuck had done to him. Jack had only wanted Bass Industries. That was all he had wanted and they had taken that away from him. He had slaved away in Australia all these years in the shadow of his brother in hopes that he would one day be able to run Bass Industries himself. It was all he had. He could only concentrate on his career. The love of his life had left him years ago because he had pushed her too far. She had put up with his boozing and womanizing ways for too long. In a way, Chuck was following in his footsteps. There was no harm in taking away Blair from him now. She was bound to leave him eventually anyway. Besides, he wanted to remember what it was like to be with a girl like Blair Waldorf. She reminded him so much of his old flame.

"Blair, I have a surprise for you..." he murmured as he entered her room.

There was no reply. All he heard was the sound of retching behind running water. He knew about her problem. It had happened that night as well when he had tried to charm her. She had been too preoccupied with her activities, however, to notice his advances.

Suddenly, he felt a foreign tug on his heart and his intention of revenge slowly escaped from his mind. For some odd reason or another, he wanted to hold her in his arms and tell her that he was here for her – that he could melt away her pain. He approached the bathroom with caution and slowly turned the knob on the door. The clicking sound it produced caused Blair to turn around abruptly. She was sitting on the floor. There were tears in her eyes and evidence of the contents of her stomach lingered on her delicate mouth. Jack felt his own stomach coil at the sight of her. How could Chuck let someone like this hurt so much because of him? He was in no position to judge, of course. He had done the same to his lover years ago.

"Jack, what the hell are you doing here? I thought we sent you back to Australia," she spat, willing for him to leave.

Jack did not respond and merely offered her a hand to help her up. Blair hesitated, but eventually took it. She walked over to the sink and began brushing her teeth, evading his intent gaze upon her. They reminded Blair too much of that Chuck Basstard.

"Jack, I asked why you were here," Blair restated with less tension in her voice this time.

She was tired of putting up a strong front in the presence of others. Jack already knew of her relapse. She had nothing to lose with him.

Jack turned his mouth up into a signature Bass smirk. "I was going to try and seduce you to have my revenge on my dear nephew for sending me away..." he trailed off for an added effect.

Blair rolled her eyes. "I am not sleeping with you Jack, so you can forget it."

Jack let out a genuine laugh. She was one hell of a girl alright.

"...but now...I simply want to take you out for the night," he finished.

Blair quirked an eyebrow in his direction, curious as to his reason for the change in plans. Bass men always had their way. They never changed their plans for anyone. Jack could see the curiosity and caution etched upon her face. He let out a loud sigh.

"I know that may be hard to believe, but I think you could use a night out. One night to forget all the pain, Blair," he said, turning her around, so he could look into her eyes properly.

Blair thought this over. She had told Chuck that she was done with him and she could use one night to escape from the world, but she couldn't help but wonder about his ulterior motives.

"I am dead serious Blair. We can go to a slightly more public restaurant, so you can feel safe with me. You can bring Dorota along for the added protection," he joked, trying to put her at ease.

Blair tried hard to mask a smile, but was unsuccessful. Why was it so hard for Chuck to make her happy? All she wanted to know was what he felt about her. Was that too much to ask? How much longer would she have to wait for them to hold hands or to go to the movies together? She had learned to suppress her expectations, but Jack was offering her all of that right now for one night without the slightest hint of hesitation.

"One night Jack, but..."

Jack raised his hand to interrupt her. "I will not make a move on you Blair. You have my word."

She hooked her arm through his as he led her out of the building, guiding her towards the limo. Blair pulled back slightly and Jack immediately sensed her discomfort.

"Is something wrong Blair?" he asked, genuinely concerned.

He had no idea why he was such a gentleman around Blair Waldorf. She had a grasp on him that was simply unexplainable. It had been that way with his former lover as well, but his memory of Audrey had tarnished long ago.

"I know this might sound insane, but I would prefer walking to the restaurant. Limos remind me of him," she explained.

Jack understood completely where her concern was. His goal was to waltz her away from her memories for just one night and he would do anything to achieve this.

"Yes, we can walk," he replied.

As they walked down the streets of Manhattan, they remained silent. Blair was still slightly uncomfortable with the whole situation and Jack was still contemplating on why Bass men always realized what they had only when they had finally lost it. He deduced that it had to be a curse on the family name.

Blair broke the silence once they had arrived at the restaurant and settled themselves at the table nearest to the door. Jack knew that Blair was still wary about spending her time with him and this seating arrangement would provide her with an emergency escape route.

"You provided me with an emergency escape route. Jack Bass is actually not making a move on me tonight. Now, I really do believe in miracles," she teased, starting to relax in his presence.

Jack let out a grin. "Well, I am a man of my word as hard as that may be to believe. I am genuinely sorry for what I did when I was last here, but who would believe me really? I simply follow the path that I have been expected to follow. I am expected to be heartless and bitter, so I am. Of course, there are times when I am genuinely evil," he smirked, giving her a playful wink.

Blair felt a twinge of sadness for him. She knew what that feeling was like. She had never been perfect enough for anyone. Jack was expected to indulge in his evil ways, and so he did, just as she constantly strived to reach perfection.

"You know, the only reason I want Bass Industries is because the company is the only thing I have left. Bart always took everything from me. I lived in his shadow my entire life," Jack continued.

He had no idea why he was confessing all of this to Blair Waldorf, but he knew she was often in the same position. Much to his surprise, Blair opened up about living in the shadow of her mother and her best friend, Serena.

"I know how hard that is Jack. I have never been perfect enough for my mother and I constantly live in the shadows of my best friend. The boys at school are always more entranced with her than with me and the girls are as well. Serena could take my position as queen any day of the week without so much as lifting a finger."

Jack put his hand over hers. "You are beautiful, Blair. I know Chuck thinks so too. The way he looks at you is evidence enough."

Blair pulled away from his touch and looked up from her food, searching his eyes for sympathy. Blair Waldorf needed no one to sympathize with her. She was stronger than that, but there was no sympathy in his dark eyes. She saw only respect and a truth to what he was saying. This pleased her, although she would never openly admit it. They continued to ramble on about their lives, opening up to each other in an environment where one would not judge and would not be judged in return. It was a relief for both of them. Jack could feel the wall he had built around his heart disintegrate as he forced out each and every word and Blair was happy that she could detach herself from her pain if only momentarily.

"Thank you Jack," Blair blurted out on a whim as she walked beside him later that night.

Jack could only nod. He knew this night would have to end. They had to return to their respective realities. He knew Blair loved Chuck and he had had his opportunity to love someone unconditionally a long time ago. He secretly hoped that his nephew would see what he was throwing away soon before it would leave him forever and haunt him for the rest of his life. Despite his reputation, Jack did have a heart and somehow Blair Waldorf had been the one to show him that.

"You're welcome Blair," he responded as they arrived at her building.

He turned towards her as the air thickened around them.

"Blair..." he whispered.

At that moment, she knew he was about to break his promise. She knew he had had an ulterior motive in mind! All Bass men did!

"I am not sleeping with you Jack," she spat, ruining the evening.

She instantly regretted her assumption because she witnessed his face fall with hurt.

"I actually wanted to thank you for not judging me tonight, but..."

"I am so sorry Jack," Blair interrupted, trying to salvage the evening.

"No, I deserved that. I would have expected that of me as well," he insisted.

The last thing he wanted was for her to return to her bathroom and purge because she felt horrible about herself. Blair merely nodded and began to walk away from him.

Jack knew he should make this offer now. It was now or never.

"Blair, I'm leaving for Australia tomorrow," he shouted after her.

Blair paused and turned around to face him, waiting for him to elaborate.

"You can come with me. You could use a few days of vacation, right?" he asked, hoping that she would consider his offer.

"Thanks Jack, but no thanks. Tonight was great, but..."

"There are no strings attached Blair and I still intend to keep my hands to myself," he assured her.

Blair shook her head in response and ran into the building before he could stop her again. Jack waited until she had retreated into the building and turned to walk away in the opposite direction. He understood what she was concerned about. He knew from the single glance she had given him with her chocolate eyes.

Tonight had been wonderful, but it had left him with a strong feeling of regret. If there was one thing he could do all over again, he would never have let Audrey walk away from him on that day. He would never forget what she had said to him for as long as he lived. I'm done. Those had been her exact words and they had burned a permanent hole in his heart. Those words would follow him for the rest of his life.

Blair watched him walk away from her window. Truthfully, she had been tempted to take his offer. A vacation with no strings attached was just what she needed. Tonight had been so raw and genuine. She wished that one day, she would be able to experience this with Chuck. There would be no more need for games. The concrete walls they had built around themselves would come crashing down and there would be no more pressure for him to say those three magical words anymore because he would be reminding her of them every day.

Tonight, Jack had given her hope. He had told her about Audrey and she was amazed to find that Audrey had been so much like her. She had been in the same predicament and Jack had allowed her to walk away because he had convinced himself that she was better off without him. Chuck had allowed her to walk away as well when she had declared that she was done with him, but as Blair turned off the lights to retire to bed for the night, a new realization dawned upon her. Blair Waldorf would show Chuck Bass that he was worthy of her unconditional love. He was broken and Blair would need to fix him before they could embark on their future together. She would have to push her hopes and desires aside for now. Who knew that Jack Bass, of all people, would have made her realize that? She drew in a calming breath and closed her eyes, willing herself to drift off to sleep. Blair Waldorf would never allow for Chuck Bass to ever let her go.

Jack felt the wind being knocked out of him as someone shoved him up against the brick wall.

"I thought I sent you back to Australia," Chuck seethed, pinning his uncle against the side of the building.

Jack remained calm and simply shrugged off his angry nephew.

"Charles, to what do I owe this pleasure?" he drawled.

"Cut the crap, Jack. What are you planning with Blair? You leave her the fuck alone or I'll rip you apart with my fucking bare hands!" Chuck shouted, unable to control his emotions.

He always lost control when it involved Blair. Chuck grunted. Blair Waldorf would be the death of him. Jack merely responded to his threat with a single smirk – one that Chuck knew all too well.

"I had no idea having dinner with a friend was a crime in New York, Charles. I'll try to restrain myself from talking a walk on the wild side the next time around," he said, sarcasm evident in his voice.

Chuck took a step back from his uncle and lowered his eyes, wrapping each of his hands into a tight fist.

"Please. Just leave her alone," Chuck managed to choke out in a soft whisper, his voice drenched in defeat.

Jack opened his mouth, intent on saying something that would make his nephew explode with even more rage, but he couldn't bring himself to do it. He let out a frustrated sigh.

"Chuck, nothing happened between me and Blair nor will it ever. You have a good thing going for you, you know?"

Chuck looked up at Jack, shocked at his response to his plea. He would have expected Jack to use his current weakness to his advantage, but all he could see was the sadness and regret in his eyes. Was he hearing things? It was as if Jack Bass actually gave a shit.

"I caught her purging in her bathroom again, you know? While you were wasting away in Bangkok, she had a relapse. It was her way of relieving herself of her pain. I was just taking her to dinner tonight to offer her an escape from it all if only for a brief moment," Jack revealed.

Chuck felt the world crumble around him. At that moment, he hated himself so much. How could he bring so much pain to someone he loved so damn much? She was better off without him. Chuck Bass did not deserve a girl like Blair Waldorf.

"You are good enough for her Chuck. She believes that, so why don't you?"

Chuck looked up at his uncle. What? How did he know he was...

"I'm a Bass too," Jack stated, reading his mind. "I know how your mind works. Look, I'm going back to Australia for good tomorrow. You have nothing to worry about. I'll return to my crappy excuse for an office and stay there. I'll leave you and Blair and everyone else on the Upper East Side alone. Just don't let her go, Chuck. You'll regret it when you get to be my age. Take it from someone who knows."

Chuck remained silent as he tried to wrap his head around the fact that Jack actually had a softer side to him. He had to be dreaming. He was acting completely out of character, but somehow he could sense that his uncle had meant every word that was coming from his mouth. Witnessing his facial expression, Jack knew that he had gotten the message across to his nephew. He shoved his hands into his pockets and slowly turned to leave.

"Jack, I can arrange for..."

Jack waved his hand at the offer he knew Chuck was prepared to give him.

"Forget it, Charles. This is your life to live and enjoy surrounded by the people who love you. I had my shot at a life like this a hell of a long time ago," he said, a somber expression upon his fallen face.

Chuck nodded and watched his uncle's retreating figure. For some reason, he felt his previous hatred towards him slowly fade away. He turned around and walked in the opposite direction.

Was he really worthy of Blair? Could they really do all of the things that normal couples did without changing who they were? He wished that one day, there would be no more need for games. The concrete walls they had built around themselves would come crashing down and there would be no more pressure in saying those three magical words anymore because he would be reminding her of them every day.

Tonight, Jack had given him hope. Chuck had allowed Blair to walk away that night when she had declared that she was done with him, but as he climbed back into his limo, a new realization dawned upon him. He would teach himself that Chuck Bass was worthy of her unconditional love. He was broken and he would need to fix himself before they could embark on their future together. Who knew that Jack Bass, of all people, would have made him realize that? He drew in a calming breath and closed his eyes, resting his forehead against the window. Chuck Bass would never allow for Blair Waldorf to ever let him go.