A/N: This idea came to me last night and I just couldn't not write it down. As we have seen in the show, I know there is no way, no how that this is the way Red came about knowing Lizzie but I still love the idea!

Takes place in the Madeline Pratt episode.

Disclaimer: I own nothing…wish I did, but I don't.


Why Red Didn't Go To Florence:

"Was any of it true, Raymond?" Madeline whispered to Red through the bars of her cell. "The story? Was any of it true?"

Red stared back at her, silent.

"Do you really want to know, Maddie? About why I didn't show up in Florence? The absolute truth?" Red said softly.

"Yes. You owe me that," Madeline said locking eyes with Red.

"I owe you nothing after what you have done," Red said in his unmistakable deep voice.

Madeline's hands grasped the cell bars tightly as she stared angrily at him.

"But as you and I won't be seeing each other again, I'll tell you why. The honest truth," Red said to her as he slowly walked closer to the bars.

"Do you remember the morning I left Sydney? I told you I had some business in New York but after that I would meet you in Florence. One, maybe two days max. Do you remember?" Red said, never breaking eye contact.

"Of course I remember," Madeline replied softly. She could feel her heart breaking as the memory re-played for the thousandth time in her head. She could see everything about that morning. Sitting across from each other on the balcony of the hotel room that overlooked downtown Sydney, how handsome Raymond looked in his new three piece navy blue suit, how delicious their Belgian waffles tasted, the way her green silk robe felt against her skin. She replayed that morning time and time again in her head. What had happened? What did she say, what did she do that made him change his mind. It's haunted her and that day has never been far from her thoughts.

Standing at the hotel room door, Dembe waiting on the other side of it. Raymond's arms around her, making her feel safe and wanted. "I'll meet you in Florence, Maddie. Wait for me. I'll do my best to hurry," Raymond had said before bending down and kissing her deeply. He then unwrapped his arms, letting her go, he put on his hat and turned the door knob. She watched him walk down the hall with Dembe at his side. Watched them both get into the elevator and as the doors closed, Raymond looked up, locked eyes with her and gave her a wink.

That was the last time she saw Raymond Reddington. Life had been perfect.

Red sighed deeply as he stared at Madeline.

"Well that's true. I did have business in New York. Dembe and I did go there. We arrived, took care of business and were headed back to the air strip to board my plane," Red said to her. "Traffic was horrible of course. We were at a red light and had been for several minutes. I was sitting in the backseat and was going over some paperwork from the meeting I had. For whatever reason, I raised my head up and looked out the window to my right. And that's when I saw her."

Madeline, who was hanging on every word Red was saying, said, "Saw her? Saw who?"

"Elizabeth Dawn Keen. You know her as Nicole," Red said, never breaking eye contact.

Oh my God, Madeline thought still looking at Red.

"I saw Lizzie walk out of the Starbucks on the corner. She was carrying her coffee cup in one hand and looking down at her phone in the other. As she stepped out of the door, she walked a little ways to her left before she stopped again. Her eyes never leaving her phone. I remember everything about that moment." Red said, his eyes glazing over as he remembered that day.

"She was wearing these lightly faded jeans, a black top and the most god-awful olive colored jacket!" Red said with a small laugh. "I don't know what it is about her liking the color olive! Lizzie has many fine qualities but knowing what looks good on her just isn't one of them," Red said shaking his head with a smile.

"Right at that moment, the light had turned green. Dembe was just stepping on the gas when I told him to pull over, never taking my eyes off of her. Thankfully no one was parked on the side of the street and Dembe parked the car at the curb. As we sat there, my eyes never left her. She was the most beautiful thing I had ever seen. Her hair light brown with these blonde highlights. She had very little make-up on. She was so beautiful. I couldn't stop staring at her. As she was looking down at her phone, I guess it had rang because she suddenly started smiling. A gorgeous smile. I rolled down the window a little bit. I wanted to hear her voice, just once," Red said staring off in the distance.

"Hi daddy, she had said into the phone. Her voice so light and….happy. I couldn't tell you what else she said because I wasn't paying any attention. I just couldn't stop looking at her. I found I couldn't help but to compare her with my wife," Red said with a small smile on his face.

"They look nothing alike and are nothing alike. Lizzie has brown hair, Trish had blonde. Lizzie is about my height, Trish barely reached my shoulders. Lizzie exercises practically everyday. Trish hated working out and only did when her jeans were getting too tight," Red said with a laugh. "Looks wise, personality, likes, dislikes, habits, hobbies, interests. You name it. They are complete and total opposites and yet…the same. Both have such strength and determination, neither would ever back down from anything. So protective of the people they loved. Both would stand and fight. To the bitter, bloody end."

Madeline never said a word. Just listened and stared at him through the bars.

"Their ability to forgive," Red said. "Yes, they both could and can get angry. Very angry. But they will always find it in themselves to forgive. To give second chances. To stand by those who people have written off."

Madeline knew Raymond was talking about himself. She watched as Red shook his head slightly and looked down at his hat in his hands. He suddenly looked up and met her eyes.

"That's why I didn't show up in Florence. She is the reason. I saw her and I knew I had to know everything about her. That's the moment I became obsessed with Elizabeth Keen," Red said.

"She finally hung up the phone and started walking away. I immediately got out of the car and Dembe and I followed behind her. We followed her to her apartment building a couple of blocks away and as she went inside I told Dembe to get someone on her. To follow her, protect her, to find out everything about her. I told him to get me a room in the closest hotel to her that he could get. I felt like I was outside of my body. All I could think about was her. Dembe reminded me that I was due in Florence and that's when I suddenly came back to Earth," Red said as he looked into Madeline eyes. "I want you to know I never meant for any of that to happen. I really was planning to meet you," Red said as he frowned slightly.

"I know what I did was wrong. I know I should have gone to Florence, even if it was just to tell you it was off. I know I should have been straightforward with you. I know I was a selfish bastard to you. I know I did you wrong and I want you to know one thing," Red said taking another step forward. His eyes never leaving hers. "I. Am. Sorry Madeline. I. Was. Wrong."

Madeline couldn't look away from Red. Tears slowly running down her cheeks.

Red pulled out a stark white handkerchief from his inside suit pocket and handed it to her. "I know this probably won't make you feel any better but Elizabeth and I are not together. Never have been. After Dembe found out everything about her. Where she was from, what she did, who she knows. I know I'm older than she is so I knew I was going to have to be very creative when I finally did introduced myself to her but when I found out everything about her my plans changed completely. It was over a year before we finally met face to face. Nothing has happened between us. In fact she can barely stand me," Red said with laugh. "I also know things between us may never turn out the way I want them to."

"If you aren't with her then why can't we be together? I don't care if you have feelings for her. If you know she doesn't see you in that way, why can't we still be together, Raymond?" Madeline asked looking at him, begging him.

"She's the kind of girl who would never break up a couple. I would rather live the rest of my life, however long that is, knowing that maybe something could happen with her then knowing for a fact nothing ever would. As long as I'm in her life, in some way, I'm happy," Red said.

She could feel her heart breaking all over again. She knew he meant what he said. She just couldn't believe after everything they shared with each other, this is how it was ending. Truly ending. She wasn't getting Raymond back.

"Thank you for being honest with me Raymond, " Madeline said.

Red nodded as he looked at her. After a brief silence he said, "And that's why I'm not going to kill you Madeline. I should after all you have done. I've killed people for far less in fact. But I won't."

Madeline stared back at him slightly in shock. She knew what he was saying was true. He had killed for less.

"I did you wrong and you were acting out in revenge. I'm going to let you go," Red said to her before turning and nodding to Dembe. Dembe came out of the shadows and walked to Madeline's cell, unlocking it before stepping back away.

"Thank you Raymond," Madeline said looking up at him with love in her eyes.

"But know this Madeline. You ever steal from me, attack me, plan against me ever again. I. Will. Kill. You. Do you understand?" Red said deeply as he looked at her.

"Yes," Madeline said softly, looking up at him.

"You are never to contact me or mine ever again. In any way. I meant what I said, I don't ever want to see you again. Move on with you life," Red said.

Madeline nodded before saying, "I will always be waiting for you in Florence, Raymond. If you ever change your mind."

Red sighed before turning and walking away.

As Madeline watched him walk down the long, dark underground hallway, out of her life, tears started streaming down her face again but she did feel better knowing it wasn't something she had done to make him walk away after all and maybe one day, someday, Raymond would come back to her.

The End!

A/N: Since they haven't said what Lizzie's middle name is or what was Red's wife's name, I just made them both up. Would love to know what you all think. Review :)