AN: I forgot to mention that Ellie and Liz Bartlett are not in this story.

Leo sat in his office trying to make since of everything that had happened that weekend, Monday had finally come around and he knew that Jess would be teaching her first classes today. There it is again. Why can I not stop thinking about her? She is after all fifteen years my junior, and to make matters worse, she is the daughter of my best friend, and the president of the United States. Leo caught himself touching his lips softly, and pulled his hand away as if he had been burned. It had been like this since Jess had first kissed him, and he was way out of his depth on what to do. Finally with an angry sigh he raised himself out of his chair and made his way to his doom.

"Hey CJ, can I borrow you for a moment" Leo asked as he entered CJ's office.

"Sure Leopold, what's up?"

"Um… Can I close the door?"

CJ nodded "is everything alright, Leo?"

"I wanted to get your advice on a very personal matter."

"Okay, shoot."

"Well. Um… right before Jess left to head to Scotland, she, well she kissed me" Leo stuttered blushing the whole time.

"So, what's the problem" CJ asked

"What's the problem? The problem is that she kissed me and, not just that, but also I enjoyed it. More than I should have, what with her being my best friend's daughter, and the First Daughter of the United States."

"Is that a real thing?"

"What" Leo asked.

"First Daughter, oh never mind. So you like Jess, and I know for a fat that Jess has the hots for you"

"How could you possible know that?"

"She told me, Leo. Jess loves you, but she thinks you still see her as a little kid, and as your daughter's almost older sister."

"What exactly did she say?"

"Leo you are being ridiculous; she said that she loved you very much and that she had for a long time, but she was afraid you saw her as an immature child."

"That's absurd, I never saw her that way."

"Then show her that. Send her a letter or something with their family owl."

Leo nodded and headed to the door "thanks for your help CJ" he said as he stopped short of the door, and made his way to his office. Once he reached the office and sat at his desk, he pulled out a piece of paper and began to write.

Jessica Bartlett,

Jess this is one of the most nerve wracking experiences of my life; seems foolish doesn't it. I have not been able to quit thinking about you since you left, since you kissed me. I really wanted to have this conversation in person, but I don't think I could have waited until Christmas to talk to you about it. I am so afraid to have taken this the wrong way, but I cannot be a coward anymore. I need to know if it meant what I hope it meant, because you see Jess, I have never seen you as a child, or like you were just my daughter's playmate. It took me a long time to admit it even to myself, but the truth is Jess, I care about you, and far more than I should. You were 21 the day I fell hopelessly in love with you, but it was not until the day that Jenny gave me the ultimatum that I realized that I love you. Don't get me wrong, I am in no way saying that I left Jenny because of you, and nothing that followed that day was your fault. I left Jenny because I knew then that it would only hurt more in the long run to try and continue the farce of a marriage we had put forth for so many years. I am rambling now, but I guess what I am trying to say is this: I am very glad you kissed me, and I love you very much, and I hope when you return at Christmas you will give me a chance to show you how I feel.

With Love,

Leo McGarry

Leo gave a heavy sigh and folded the letter up and placed it in an envelope that had been addressed with Jess's name and the school's name, but he could not bring himself to send it. He stood and walked down the hall a bit to ask Mrs. Landingham if the President was free. At her nod he let himself into the office.

"Hey, Leo come on in. I haven't seen much of you in the last few days." Jed said with a smile

"I've been somewhat distracted. I wanted to talk to you about something thought."

"Ah, sounds important, what's up"

"Um... honestly Jed, I don't know where to start with this one. Do you remember Jess's twenty-first birthday party?"

"Ohh yes, I was ready to kill her that day, but with everything that had happened that day, with her friends I mean, I just didn't have the heart."

"Jed, I, or rather, um…"

"Leo what's wrong, you never get nervous like this"

Leo sighed "Before Jess left she, well, she kissed, on the lips. And I was talking to CJ and she said that a sometime before that Jess had told her that she, well that she liked me and – god this is awkward. Jed, I really like your daughter, and I was hoping for permission to try and court her."

"Leo, you're blushing."

"Yes, sir"

"No Leo, I'm still Jed for now. Leo, I am very protective of my daughters, both of them, however, you are my friend and I trust you not to do anything to hurt Jess, so I will give you permission and a warning. I am the Commander-in-Chief of the United States military, and if anything happens to her, if you break her heart, I will break your neck."

Leo nodded "Completely understood Jed, and thanks"

With a weight lifted off of his chest Leo sent the letter and prayed that Jess would give him a chance.