A/N: Sorry it's taken so long to update this, but I was in Europe for months with no internet. I've got the next few chapters written out and ready, but I need to type them up and publish them. This is a little short, but I feel like it's a major plot point that needs to be included. The next chapter should be put up next Sunday morning.

Adrian Monk had every moment planned out perfectly from the time Natalie was set to arrive to when they would say goodbye. Except for one major, well for Adrian Monk, major part. He didn't know if Trudy would approve of this. Sure, she'd died 10 years ago, but he hadn't solved her murder yet and it haunted him. It haunted him more than his fear that everyone would leave him. Even Trudy left him, though due to extremely unfortunate circumstances.

"Oh Trudy, what have I done? I haven't even solved your murder, yet here I am about to go on a date with another woman."

He put his head in his hands and began to cry; tears for losing Trudy and for not being able to solve her murder. As he sat wallowing in his misery the atmosphere in the room changed. SHE was there.

"Adrian, darling, don't cry. Now tell me what's bothering you my love." Trudy spoke as she gently caressed his face and rubbed his back.

Adrian looked morosely at his wife and began to speak, "I'm moving on. I think. I've got a date, sort of, with my assistant Natalie and I haven't even solved your murder yet. I'm a horrible detective if I can't even solve your case. I haven't solved it and yet I'm having…. Feelings for another woman! For Natalie!" he exclaimed, getting frustrated with himself.

Trudy smiled at her husband knowingly and began to speak, "Oh sweetie. You can move on; should move on. Do you think I've wanted to see you spend every day of the past 12 years in mourning for me, unable to function? I've been hoping you would move on and watched you grow closer to Natalie hoping you would do this very thing. If you'd died you'd have wanted me to move on and be happy if you died, I know you would. Be happy Adrian. Then you'll know who my love."

"But I can't be happy. You were my one chance at that." he quipped, not wanting to admit that she was right.

"Do you really believe that Adrian? Or are you scared to move on from what you've known? You can be happy again. The key is, well you're starting to find out. Now take off that ring and go be happy."

"Trudy," Monk sighed, looking at his left hand and finding he didn't feel compelled to wear it on his hand, "Okay, I'll try. But I'm not sure I can be happy."

"Promise me you'll try my love."

"I promise." With those words Trudy gave one last smile and vanished into thin air. He turned to his hand again and took the ring off. Monk looked at it and didn't want to put it away just yet.

'Don't worry,' a ghostly voice whispered, 'There will be another one there soon.' Monk shook his head and walked towards his room.

He went to Trudy's jewelry drawer and grabbed a fine chain, brushing past the velvet box that contained her engagement ring and put the ring on. It was hanging around his neck, tucked under his shirt collar. He then went to go wash his hands from the dirt that had accumulated, despite having washed them just 10 minutes previously.

As he returned to the couch he noticed the house seemed to be brighter and maybe a little happier than usual.

The apartment was unusually silent, even for Monk's standards, which worried Natalie even more as she walked into his apartment at 10 am, instead of 8.

"Hello?"

There was no sign of her boss until she entered the living room, where she found him leaning back against the couch with his hands behind his head, asleep. Content; with a smile on his face.

"Mr. Monk? Adrian?" Natalie called, slightly worried now that he hadn't heard her come in because he was usually a light sleeper with the slightest sound waking him up. She walked up to him, and convinced he was simply asleep, and nothing was horribly wrong with him began to study his face.

There was a peace there that Natalie had not seen on it, well, ever. It made him look years younger, without a single line of worry marring his handsome visage. Natalie walked up to him and gave his shoulder a gentle shake.

"Adrian," she called, "time to wake up." The movement did the trick. Within moments he was awake and staring up at Natalie.

"Na-Natalie? What are you doing here? It's only 8-" Monk blinked twice as he saw the clock. 10:12 am.

'I've been asleep for two hours?' Monk thought, slightly confused but more worried now that his plan would have to be enacted.

"Oh." Monk said, standing up in front of Natalie, just inches away.

Natalie felt her face flush as Adrian stood in front of her, his lips just a few inches away. She longed to kiss him now, but knew that would not lead to anything good. She turned away from him, taking a step towards the kitchen.

"I'll go make some coffee." She mumbled, rushing away.

Adrian was confused. Why had Natalie run off, blushing? To the kitchen. THE KITCHEN! He couldn't let her see the kitchen; it would ruin the perfect surprise he had planned.

"Natalie!" His voice was panicked now, "Don't go in the kitchen! It's… I need to clean out the fridge. Just wait in the office. Please." He added, dashing to intercept her. It was too late. Natalie had entered the kitchen.

"Mr.- Adrian? What's all this?" she asked, waving her hand in the direction of the food, flowers, and chocolates he had on the counter. Monk walked into the kitchen his face turning slightly red now.

"It's, a um…" he breathed deeply before trying again. "Happy Valentines Day?" he asked, running his finger over his eyebrow and straightening the collar of his shirt. He re-buttoned the top, then un buttoned it again. He was fidgety now, trying to straighten everything within reach while keeping himself from looking at Natalie.

Natalie's hand reached to cover her open mouth. He'd been trying to give her a Valentine's surprise. Her face turned red again and her eyes started to water. Monk looked at her then.

"Nat-Natalie? Did I do something wrong? I knew I shouldn't have… You'd never feel that-"

"No, Adrian. It's perfect." She said giving him a watery smile.

"Then why are you crying? You don't have to lie to make me feel better, you know." He said, turning around in a defeated motion. "You can go home if you want to." He started to walk away; saddened that Trudy had been wrong about it. He knew it was too good to be true. He stopped walking when he felt a hand grab his.

"Really Adrian, it's beautiful." Natalie said, stepping in front of him and squeezing his hand. "I just wasn't expecting you to get me such a big gift. You didn't have to you know. A card is good enough for a friend." She smiled and gave him an unexpected hug. Even more surprising then the fact that he didn't move away was the fact that Monk, Adrian Monk, wrapped his arms around Natalie and hugged her back.

"Natalie," Monk began, "you're more than my friend. You're my ass…partner and my best friend too-" He stopped speaking suddenly, searching for the right words to tell Natalie exactly what she was, but finding none, was at a loss. A voice, long dormant in his mind told him the right thing to do to show Natalie how much she meant to him would be to kiss her, but he wasn't sure how she would react to that.

Natalie was enthralled with the feeling of being in his arms, her head resting against his chest, as she knew that this was difficult for him and might never happen again. She had imagined it for so long now, wanted it to be a reality at least since Sparks had happened; even more so after the night she'd spent with him. 'No.' she firmly told herself. 'I'm not even going to go there. It's inappropriate to think of him that way. He'd never feel that way, much less kiss me.'

She felt him stiffen slightly and let go, figuring he was getting uncomfortable with the hug and looked up at him. Monk had a far away look in his eyes, as if he was thinking about Trudy or trying to remember something. He took a deep breath and relaxed again, looking at Natalie.

His voice was shaky and nervous. "Natalie, would you mind if we… danced?"

She felt herself grow excited with each word, until he said dance. She was hoping he would, well, kiss her. But dancing was still better than not being near him at all.

"I-of course." Natalie replied, her voice sounding slightly disappointed.

Natalie smiled at Monk who went to put on the music. He mentally shook his head. 'You should have just kissed her. She wanted you too.' The thought shocked him, but when he thought about her disappointment it made sense. 'Natalie wants to kiss me.' He thought, happier now.

Smiling, Monk pushed the CD into the player and turned the volume to about half way. He held out a hand to Natalie and they began to dance.

Natalie gasped as the song came on. It was the very first one that they'd ever danced to, at a friends wedding just over a year ago.

"You remembered?" she asked.

"Natalie," Monk sighed, "I remember everything. Photographic memory, remember." Monk grinned at the pun and pulled Natalie closer.

Natalie smiled, shocked at his actions. She stared at their hands, still intertwined, and noticed that his wedding ring was absent.

"Adrian," Natalie asked softly, "Where did your ring go?"

Monk smiled and shrugged. "Trudy said it was time to move on. She told me to take it off." He took his hand off of Natalie's waist and reached under the collar of his shirt. The ring glinted as a ray of sunshine hit it.

"Oh." Natalie replied, suddenly understanding. Adrian's ring fell back against his shirt and he reached a hand towards Natalie's face. He traced her cheek, down to her lips where she kissed his fingers.

Her eyes widened as she realized what she'd done.

"I'm sorry Adr-" her words were cut off as he placed a single finger on her lips.

"Would you be totally opposed to me kissing you?" he asked, a bold move for him, as he slowly leant towards Natalie

"No." she replied, leaning in as well.