39 Blind Dates (Destiel AU)

Chapter 2

His lunch break came a little while after, and he took this opportunity to call Charlie and tell her about his experience. When he did, she squealed and started talking a mile a minute, and he couldn't even tell her his name, because she was too busy talking about the handsome stranger and Dean's future together.

He finally got a word in, but that was only to tell her that he had to get back to work, making Charlie blue.

He worked until late into the night, putting in extra hours to earn a little more money, and then returned home, where Charlie was waiting expectantly.

"Where have you been?" Charlie asked, her foot tapping threateningly. Dean sighed, kicking off his shoes and shrugged, uncommitted.

"Well, when you were working, I found you another blind date," Charlie said triumphantly.

"You're over the handsome stranger pretty fast," was all Dean could say, trying to conceal his dismay about having to go to yet another blind date. He had gone to four all ready, and that was more than enough.

"Well, I wanted to get you a backup plan," Charlie said, and the tapping stopped.

"Okay, okay. When?" Dean asked, changing in the bathroom, but leaving the door slightly ajar so he could continue the conversation.

"Tomorrow night," she answered, and Dean bit back a groan.

"Tomorrow?" Dean asked, emerging from the bathroom. Charlie nodded. Dean held back a sigh and nodded, trying to look excited for Charlie's sake, because he knew how hard she has been trying.

They only watched a lone Doctor Who episode that night, because Charlie was getting up extra early so she could meet her "friend" (Dean personally thought there was more going on), Dorothy. Dean got ready for bed and trudged to his bedroom, flopping on his bed, smiling at the memory of Castiel.

Work flew by the next day, then he was stuck going to yet another blind date. He wore a black t-shirt with a red jacket topped over it, as well as his dad's old leather jacket. He didn't smile at the memory of his father, but felt respect. His father, Sam, and Dean had constantly moved around during the Winchester brother's childhoods, and they never really had lasting friends. Their father had been always been a traveler after their mother, and he simply couldn't give up the life, until he committed suicide, leaving Sam and Dean orphans, because their mother had been killed in a devastating house fire a couple of years prior. Then John's good friend and like an uncle to them, Bobby, took them under his wing.

Anyways, he got into Baby, and drove to the same restaurant that he had been on with Jake. He was early yet again, and he sat alone for about ten minutes until he saw a woman practically bound into the restaurant, looking very excited indeed.

"Dean?" She asked loudly, looking around.

Dean raised his hand politely, smiling. She flounced over, sticking her hand out, smiling. Dean took it, and tried to smile back, but somehow couldn't muster a convincing one.

The same waitress from his last date came up to them, shooting Dean a curious look, but he wouldn't meet her eyes, just ordering the same thing that he had before, as well as no drinks besides water.

The girl, Linda, ordered only a salad, and Dean mentally ticked one of the deal breakers that he had collected by meeting new people and their... Peculiar habits. He was a warrior, not a rabbit, and he LOVED meat, and probably would clash with a vegetarian or a vegan.

"So, Dean, what do you do?" Linda asked, taking a sip of her water, but never taking her eyes off of Dean.

"I'm an artist, but sometimes do photography, and I work at a coffee shop for extra dough," Dean answered. "What about you?"

"I'm actually becoming an attorney," Linda said.

"Nice! My brother is becoming a lawyer," Dean said, glad that they found a topic other than himself.

That conversation carried on until they acquire their food, and then the topic shifts to their hobbies. Dean learned that she enjoys tennis and scrap booking, and in turn Dean tells her that he likes fixing up cars and drawing.

The date went fairly well, but not once did Dean forget Castiel's intense blue gaze, and in his heart he knows he won't settle down until he sees Castiel again. Dean payed, and they go their separate ways, and they both agree that they really didn't feel anything click, much to Dean's relief.

Coming home, he was bombarded by questions, and again he had to see Charlie's disappointment, and his heart ached for her. She has been a real help getting him out there, and helped him break out of his shell.

Dean went to bed early with a heavy heart, trying to forgot Castiel's burning blue gaze. It was easier said than done, though.

A/N 

What did you guys think of the second chapter? It's a bit of a filler leading up the next encounter, but I think it isn't too bad. Anyways, hope you can bear through it and be on the lookout for the third chapter! Goodbye for now, my lovely hedgehogs!

Inu