AUTHOR'S NOTE: This story takes place in season 2. It's starts with TOW Ross Find's Out. Since Chandler had not really put on weight, I wanted Monica to do something else besides help him work out. This is my first fan fic so please be kind and review.

[Scene: Monica and Rachel's apartment. Everyone is sitting at the couches, Chandler enters.]

"OK, what is it about me? Do I not look fun enough? Is there something. . . repellant. . . about me?" Chandler asked quickly.

"So, how was the party?" asked Rachel.

"Well it couldn't have been worse," Chandler exclaimed. "A woman literally passed through me. OK, so what is it, am I hideously unattractive?"

"No, you are not, you are very attractive," Phoebe answered quickly. " You know what, you just need a date."

As he looked around the room to see if anyone else found the irony of her statement, Chandler fired back with "Okay, was I not speaking out-loud again?"

"Oh, you and your ways," a frustrated Phoebe shot back. "No what I mean is you should go on a practice date with one of us. And we could tell what you're doing wrong."

"You know that's not a bad idea," added Rachel.

"I'm totally good with advice," Phoebe stated confidently.

"Oh you know, I would, but I only like subjecting myself to embarrassment when there is potential for sex. I mean going on a date already knowing you won't get laid… for me… would be like ... Saturday night. So, which one of you wants to go out with me?" Chandler asked in his usual sarcastic tone.

"I would but I'm working tonight," Phoebe announced.

"I didn't know you had to work," Monica questioned.

"Oh, it's not at the office. I'm going out with Scott and let me tell you trying to get that guy to put out is work," Phoebe said in her

"Tell me about it. I had a date last week. It took me an hour to get the girl to sleep with me," Joey added.

"Anyway. Rachel, Monica?" Chandler asked.

"I can't I have a date," Rachel announced.

"You're going on a date?" a surprised Joey asked.

"Yes. Is that so surprising?" an annoyed Rachel fired back with.

"Yes." Joey quickly replied. Then, after realizing Ross was still in the room, he quickly said. "No."

"So who is this guy?" asked Ross.

"I set her up with a guy I know from work," Monica stated. "You know back when I had a job. A place to go in the morning… something to do. Oh God, Chandler I'll help you."

XXX

[SCENE: Monica and Chandler are in his apartment.]

Monica, whose unemployed status had left her in desperate need of a project, had brought enormous passion into the task of improving Chandler's dating skills. She even had created an evaluation form, which included categories like (1) Appearance, (2) Manners, (3) How Romantic the Date Was etc. Usually, Chandler would have mocked how much time she was spending on this, however it was nice to see her excited about something. And truth be told, he appreciated all the effort she was making to help him. Maybe his dating skills could improve.

"So the key to good first date is to make the date about her. Pay attention to her. If you want her to be interested in you, show an interest in her by listening to her. Be nice and don't try too hard." Monica said authoritatively to Chandler who sitting on a barstool looked very much like a student gazing at the all-knowing teacher. "And to ask her out on a first date you want to call her up a few days in advance. When you ask her out have a plan in mind of what you want to do," she said.

"Okay, I can do that," Chandler replied confidently.

"Let's try it," Monica said while tossing him the phone.

"Seriously?" replied Chandler skeptically.

"Do you want to spend Saturday night alone?" Monica shot back.

"Ring. Ring." Chandler answered sarcastically while holding his phone.

Picking up the other receiver Monica replied "Hello."

"Hi. Is this Monica?" Chandler voiced in somewhat annoyed tone.

"This is Monica. Who's this?" she asked.

"It's Chandler. You know that hot piece of ass you've been dying to have call you," he stated in a cocky tone.

Monica gives him an exasperated look.

Seeing her look, Chandler answered, "I'll just hang up on myself."

Monica nods.

XXX

[SCENE: Monica and Rachel's apartment. Monica is getting ready.]

Hearing someone knocking on the door, Monica scurried across the apartment while attempting to put her earring in. She was wearing a beautiful, knee-length red dress. She opened the door to find Chandler dressed in a sport jacket and slacks, and for the first time since that fateful thanksgiving, she noticed how handsome he was.

Chandler was equally stunned. Since the day Chandler lost a piece of toe, he had never known Monica to not look beautiful. But tonight, knowing she had put such effort to look good just for their practice date made her look amazing. Finally regaining the ability to speak, he said softly "You look beautiful, Mon."

Blushing, Monica smiled sweetly at him and then replied playfully, "Wow. No joke just a sweet and sincere comment. Are you feeling okay, Bing?"

Maybe it was because the death for Heckles just a few weeks earlier had left him with a real fear of dying alone if he couldn't get past his commitment issues. Maybe it was because he wanted Monica to feel better about herself for a few hours and not dwell on being unemployed. Or maybe it was because she just looked so damn gorgeous that he was willing to brave his fear of vulnerability if it meant she might smile at him again. But, for whatever reason, he fought every instinct he had to deflect and make a joke, and said simply, "Honestly, I feel a little like I'm in someone else's life. I'm not used to having an amazing woman agree to go out with me... and it makes me happy even if it is just a practice date."

This is why she had been secretly excited about this practice date. Every now and then it was as if Chandler could see into her soul and know exactly what she needed to hear to feel better. He had a kindness in him that could be irresistible. Of course, these revealing moments were like lightning… a quick flash and then they would disappear into a sea of jokes. That's probably why she never pushed for a deeper relationship with him.

Tonight, though, she would get to see what it would be like to date Chandler without actually having to date him. It was going to be fun.

Snapping out of her thoughts she replied, "Thank you, Chandler. Just so you know if this were a real, blind date, I would be very pleased right now."

Sensing the awkwardness that invoked him when complimented, Monica grabbed his hand quickly and said "Well enough of this mushy talk, we better get going or we'll miss our reservations."

Chandler just starred back at her in amazement and followed her out the door. Though it had just begun, this was already the best date he'd ever had.

XXX

[SCENE: Monica and Chandler are in a nice restaurant.]

"So tell me about yourself," Chandler said playfully as they received their drinks at the nice restaurant.

Monica returned his smirk knowing this was his attempt to show an interest in her as she had advised. Playing along, she told him about her childhood. She found herself revealing more than she normally did. Telling him that she felt she never quite lived up to her mother's expectations, which probably explains why she struggled in the past with her weight and in the present with relationships.

Chandler's eyes remained locked on hers the entire time. He would nod and offered up a response quietly when it was called for. Feeling a sense of empowerment from his attentiveness, Monica just continued on revealing how devastated she felt when she was fired a few weeks ago.

"Losing the job was not the worst part," she explained in a tearful voice. "It's that being independent was the one thing I had on my mom. She was never able to be financially independent or live alone. I could. When I left home, I made a promise that I would never call home to ask for money. Now I may have to and that kills me."

Chandler was at a loss. It killed him to see her upset especially over something that was not her fault. Not knowing quite what to say, he responded, "If it's any consolation, I can't imagine the restaurant world letting a chef as talented as you without out a job for long. As for making rent in the mean time, you could always borrow the money from me."

"Chandler, it's very sweet but I couldn't borrow money from you. If I couldn't pay you back right away, I'd feel guilty every time I saw you," she stated simply.

He understood. After all the six of them had just went through awkwardness regarding money when planning Ross's birthday. Money and friends just don't mix. And that's what he and Monica were…friends. Just friends. For some reason, he had to keep reminding himself that.

Still he felt inclined to mention, "Well if you change your mind, let me know. I mean now that Joey's working my banking account is approaching the level of a responsible adult. Yuck."

She smiled at his sweetness and whispered, "You know I think we should move onto another topic. We've been talking all night about my pathetic life. I want to hear about you."

"Why? This has been going so well. Hasn't it?" he asked awkwardly.

Chuckling, Monica said softly "Yes it is. But I still want to talk about you."

He knew better than to try to resist her. So he nodded reluctantly and responded, "well get ready to feel much better about yourself."

He told her things about his childhood she never heard before. Including how he could never rely on his parents to be there for him the ways most kids could. It was as if their roles were reversed and he had to be the parent.

As she listened intently, Monica could help but feel guilty for never realizing all the pain he had been through. She also understood why he probably struggled so much with getting close to people. He'd never seen a healthy, loving relationship. It was amazing how good a friend he was despite this.

"So that awkward boy grew into a bumbling college student; who never had much luck with the ladies until he met this girl Megan," Chandler stated. "I met her at a college party. We were both a little tipsy and just looking for someone to have fun with. Our one-night stand turned into fling and before you knew it we'd been dating six months."

Monica was a bit stunned at this revelation. She never heard of this Megan girl who obviously meant something to him.

"Anyway, for our six month anniversary I wanted to do something special. So I took her for a walk on campus, and as we arrived in front of the frat house where we had met I told her to look up. Spelled out on the windows were the words I love you Megan. It was the first time I had ever said that... or I guess, convinced some frat guys to let me write it on their windows."

"That's incredible," she said.

"Not really. I mean frat boys will do about anything if they think it will help a guy get laid," Chandler answered.

Laughing, Monica responded. "No, not that. It's very romantic. What did she say?"

"Oh, crap," he stated.

"What?" she asked.

"I said I love you. She said oh crap. Apparently, she wasn't interested in a serious relationship and had been dating a few other guys. And by few, I mean the lacrosse team," he said bitterly.

Monica was at a loss for what to say. How could a woman hurt this incredible guy so badly? Why would she be so careless and just throw a way a handsome, kind and funny guy like Chandler?

Knowing that she'd never find the right words to alleviate his pain; she finally just settled on the truth. "I'm so sorry Chandler. Clearly, Megan didn't realize or deserve what she had."

Chandler starred back at her intently. He couldn't believe he had finally told someone about Megan. And even more shocking was how good it felt to tell Monica.

Despite the breakthrough, he was still the same guy who got uncomfortable with silences or serious moments. Thus, he quickly joked, "Looks like you lost your bid to be the most pathetic person at this table huh."

He added, " And I'm guessing avoiding sob stories will be one of the things you'll suggest in my evaluation at the end of the night."

"Huh?" she asked still reeling from his revelation. For a moment, she had forgotten this was just a practice date and she was suppose to give him pointers later. She recovered quickly, "Oh, right your evaluation. Speaking of, it looks like we're the last ones here we should probably head out."

"Oh, yeah," he said. And then motioned for the waiter to bring him their check.

As they exited the restaurant, he asked if she would mind walking. Monica shook her head no since it was a nice evening. As they walked, he noticed that it had gotten cooler and quickly offered her his jacket. She accepted it appreciatively. As he placed it on her shoulders, she couldn't help but realize this was only the second time they had touched. It felt nice.

As they walked, Monica told him how she hoped Rachel's date had gone well and that she would find a way to get past her jealously toward Julie. Before Monica knew it, they were standing in front of her apartment door for the proverbial end of the night awkwardness. But, there was no need for awkwardness because this was not a real date. Right? For some reason, she wasn't sure.

"So, I want to say thanks for agreeing to go out with me," Chandler whispered sincerely.

"Oh, believe me I enjoyed it. It's nice to help someone else instead of feeling sorry for myself," she said sadly.

"Mon, I know your life isn't going quite the way you want it right now. But don't think for a minute that your pathetic. Because the truth is you're an amazing chef who will find a job. But more importantly, you're an incredible person who gave up her Saturday night to help out her annoying friend," Chandler stated confidently.

A smiling Monica was at a complete loss for words. But Chandler didn't need her to respond he went on to say, "And as if it weren't enough for you to be this talented, intelligent, kind person—you also look gorgeous tonight," he said in husky voice.

"You're quite charming when you want to be," Monica finally answered.

"Charming enough to pass your evaluation?" he asked hopefully.

Smiling and taking both his hands in hers Monica whispered, "If you act like this on all your dates, you'll never have a problem with women."

Before he could respond and ruin the moment, she kissed him softly on the cheek and let her lips linger a little longer than normal while she whispered softly, "Thank you for a wonderful evening Chandler. Sweet dreams."

She then walked in her apartment and shut the door. Despite being stunned by her sweet comments and kiss—and having no idea what it meant, Chandler couldn't help but smile. For once, uncertainty never felt so exciting.

AUTHOR'S NOTE: I think this could work as a stand alone or a series. Let me know if I should continue or not. 8