Disclaimer: I do not own any of the characters or settings of this story. Except for Lynn. Kthx.

Dedication: This story is dedicated to John - the biggest Friends/Chandler fan on the planet aside from me.

The One with Plain Jane

Chandler starts seeing a girl who is really pretty, but ends up finding out that she's very monotonous and doesn't react to anything. He ends up breaking up with her and she doesn't get mad or happy, she gets up and picks out a guy from a table and leaves with him.

"You want to find a book that was written by someone who knows what she's talking about," Chandler explained to Rachel as they flipped through the titles. "You don't want to end up putting on a mud mask that turns you into the Toxic Avenger or something."

"...The what?"

"The Toxic Avenger... we really need to spend more time together."

Suddenly, Rachel's attention was no longer on badly directed 80s movies about green, gloppy monsters. "Chandler, look at that woman."

"Which woman? We're in a bookstore where penises are completely scarce!"

"Over there." She pointed to the Drama section. "Long, dark hair, kind of pale... she's reading that Oscar Wilde play."

"Wow, she is pretty."

"Go talk to her!"

"I can't go talk to her now!"

"What, why not?"

Chandler sighed exasperatedly and pulled Rachel closer to him. "Because I can't approach a woman if I'm coming from the Health and Beauty section!"

There was a pause as Rachel thought about it. "She won't notice, she's reading. Just go!"

"Fine!" Chandler huffed. "But..."

Rachel pushed him out from behind the comfort of their bookshelf, making him stumble out into the open. Before he started for the woman, Chandler turned back to Rachel and scowled. "I loathe you."

Chandler took a deep breath. His heart was beating out of his chest and his palms were getting sweaty. He hated nothing more than asking a woman out. Ridiculously low self-esteem and impulsive were not a good mix. "So, uh, Oscar Wilde, huh?"

The woman shot her grey-blue eyes into his, looked back at the Health and Beauty section, raised her eyebrow and then looked back at him. "Yeah, the man's a genius."

"Oh, definitely."

She cocked her head to the side and squinted. "What's your favourite Wilde piece?"

Chandler noticed she was conveniently standing in front of his selection on the shelf and covering the title of the book in her hand. "Uh... Cats...?"

The woman smirked a bit. "You're cute. I'm Lynn."

"Chandler."

"Nice to meet you, Chandler." She held out her hand for him to shake, which he took gently in his own.

There was an awkward silence before he realized it was time for him to face his fears. "Oh, right! This is the part where I ask if you'd like to join me for dinner tonight."

"Do you have a piece of paper or something?"

"You can just tell me..."

"So I can give you my number."

"Right!"

"See, I told you she wouldn't care!" Rachel chuckled on their walk through the hall to Monica's apartment. "You help me pick out a new skin care book and I pick you out a new girlfriend. That's called 'karma'."

"Yeah unless you set me up with a dud, then that's called 'let's all pick on Chandler, who's such a, gosh darn, nice guy'!" Chandler retorted as Rachel opened the door to her and Monica's apartment.

"Who's a dud?" Monica cooed from the kitchen. From the smell of it, she was making some kind of chocolate and lemon dessert.

Chandler let loose a sigh. "Rachel convinced me to go up to this amazingly beautiful woman in the bookstore today. You know... I don't think she smiled once."

"She was probably just nervous. Those bookish types usually don't get approached."

Ross spun around from his spot on the sofa. "Um, excuse me?"

"You heard me." Rachel pointed out. "So Chandler, when's your date with Oscar Wilde?"

"It's Lynn. And we're going for dinner tonight; so if you'll excuse me, I have to exfoliate my pores with a nice, cleansing shower." Chandler stuck his nose in the air and strode across the hall to his apartment.

"So what do you do?" Chandler asked Lynn that night. He'd taken her to a fancy, fairly expensive Italian restaurant and they were just looking over the menus.

"I'm a journalist."

He gave an interested nod. "That's cool; what do you write about?"

"Mostly just stupid crap happening around the Village. What about you? What do you do?"

"Just an office job, I'm in data reconfiguration and statistical factoring."

Lynn didn't look impressed.

By the time they were cleaning off their dessert plates, Chandler had almost fallen asleep four times. Lynn's monotonous tone and tediously long stories that led nowhere made the fact that she was drop-dead gorgeous seem completely insignificant.

"How'd the date go?" Rachel asked without even turning to look at Chandler as he walked into his and Joey's apartment.

He forcefully spun the Barker lounger around and glared at her. "Oh, it was great." The sarcasm and look of disgust on his face proved differently. "We had a lovely meal of ice cream and rainbows, and then skipped merrily around Central Park!"

"Well what's wrong with this one?"

"She is so boring! I actually... Yes, I actually died of boredom at that dinner."

Rachel scoffed. "So are you going to see her again?"

"No! I have to break up with her before I call her again!"

"Why would you call her again?"

"Because I choked and ask her!"

"Chandler!"

"I'm going to ask her for coffee and just... and just do it."

She paused a moment and then asked, "How bad?"

"I'd rather go out with Janice for a whole year than see this Plain Jane again."

"Oh Chandler, I'm sorry."

"I hope that skin book gives you tips that turn your hair green."

Chandler entered Central Perk and looked sceptically around the shop. Lynn was already sitting on the sofa, sipping a latte. He cautiously sat next to her. "Hey Lynn."

"Chandler, I'm glad you called. I have to talk to you."

"You do?"

Lynn's eyes were darting side to side. "I'm sorry... I don't think we should see each other again."

"What, why?"

She looked Chandler in the eye and sighed. "You're... You're really boring."

"Excuse me?"

"I almost fell asleep on our last date!" she laughed. "Sorry Chandler. See you around."

Lynn got up off the couch and walked out of the coffee shop, leaving Chandler feeling simultaneously relieved and confused. "How am I boring...?"