AN: Hi, there. I thought I'd try something a little different than other stories I've written. You'll probably see some similarities, but will overall be very different. Please keep in mind that several characters may seem out of character, especially Rory. Don't hate me.

Rory sat in the office reception area nervously fidgeting and shaking her leg. She was debating whether or not to get up and bolt out the door, but she knew this was the right thing to do.

"Rory Gilmore?" A tall slender woman in her fifties called out, causing Rory to jump slightly before standing up and walking toward her. The woman opened an office door and guided Rory in before shutting the door and introducing herself. "Hi. I'm Meg Alder."She said before shaking hands with Rory. Rory looked around the room and tried to figure out where she should sit while nervously biting her lip.

"Rory, you can sit anywhere you like. The couch, the chair, behind the desk even if that makes you feel more comfortable. It's all up to you." Meg said.

"Ok, the couch will be fine. Sorry, I'm new to all this. I've never been to a therapist's office before so I'm a little nervous." Rory apologized before walking over to the couch and sitting down.

"I understand Rory, but I want to assure you that there is nothing to be nervous about. I'm not here to judge you in any way. I'm here to listen." Meg said while sitting in a chair opposite of the couch. Rory nodded and took a deep breath. "Why don't you begin with what brought you here today." Meg said while picking up a pad of paper and pen from the coffee table.

"Well, my best friend Julia said she'd come to your office a few years ago and you helped her sort some stuff out, so she recommended you." Rory said.

"Good. It's always nice to have good referrals." Meg smiled. "That still doesn't really answer the question though."

Rory nodded. "Well Meg, is it ok that I call you 'Meg'?"

"Absolutely."

"Ok, well Meg, I guess I came here because I need some help. I need some help sorting out my life right now." Rory said hesitantly. "I'm twenty-eight years old and my life is a complete mess."

"Why don't you explain that a bit more. What makes you feel like it's a mess?" Meg said encouragingly.

"Hhmm. Well, let's see, I'm twenty-eight living in New York city working in a used bookstore during the week and as a waitress in a coffee shop on the weekends. I barely make enough money to support myself and my Son. My Son is the only good thing in my life. He's nine years old and his name is Ryan." Rory said while digging through her purse for her wallet. She pulled it out and took a recent picture of Ryan out and handed it to Meg.

"He's a cute kid." Meg said while looking at the picture. Ryan stood in front of his school on what appeared to be the first day with a backpack and lunch box. He was wearing jeans and a brown cable knit sweater with a blue collared shirt. He looked a little short for his age and had bright blue eyes and very dark brown hair, almost black. Ryan had a smirk on his face that caused Meg to smile as she looked at the picture. "Although by the smirk on his face I'd say he might be a handful at times." Meg joked while handing the picture back to Rory.

Rory put the picture away while agreeing with Meg. "He can be. He gets that trait from his father."

"What don't you tell me about Ryan's father?" Meg suggested.

"That may take a while." Rory said. "Ryan's father isn't in the picture anymore. Last I heard, he was living in Philadelphia trying to get his act together again. Jess, that's Ryan's father's name, and I have a complicated history. I first met him when we were both in high school. His mom sent him to live with his uncle, who lived in Stars Hollow, a small town in Connecticut. Jess and I eventually dated, but it was short lived. His uncle did the best he could, but Jess wasn't really wanting to change his life, so he ran away after things didn't really work out. I graduated high school and went to Yale. At the end of my freshman year, Jess came back and asked me to run away with him to New York. It was completely out of the blue, but I thought I still loved him, so I went with him. Of course, my Mom completely freaked out and demanded that I come back immediately. I fought her on it all summer long which resulted in us speaking more infrequently until we finally stopped talking altogether by the time school was supposed to start." Rory explained.

"Are you and your Mother speaking now?" Meg asked.

"No." Rory answered.

"How do you feel about that?"

"Not good." Rory said honestly. "I don't know that she really wants to talk to me. We didn't leave things on good terms and I still think she's incredibly disappointed with me." Rory looked down at her shoes before quietly admitting, "You know, my Mom doesn't even know about Ryan. She has a nine year old grandson and she has no idea. I feel bad about that, but I don't think I could stand the judgment."

"Why would she judge you for having a child?" Meg asked.

Rory looked up and smiled softly. "It would be like history repeating itself. My Mom had me when she was sixteen years old." Rory clarified. "She always wanted me to have everything she didn't and preached about not having children at a young age. She'd also be very upset with Ryan's father not being a part of his life just like my father wasn't a part of mine. She wanted everything to be different for me, so I just feel like she'd be really disappointed with me."

"Did you know you were pregnant when you stopped talking with your Mom?"

"No. We stopped talking around the beginning of September. I turned nineteen in October and Ryan was born the next year in August. I wasn't planning on getting pregnant, but it happened. Jess and I were living in a cheap crappy apartment in a bad part of town and we didn't really have any money. I don't even remember how we made it work. We were so young and stupid." Rory said while shaking her head.

"So, what happened? How did you get from there to here?" Meg said.

"Jess worked and tried to support us, but he seemed to be growing more and more distant. I kept questioning him on what was bothering him, but he just got mad and more irritable. I eventually found out that he'd started using drugs again, which led to more arguing between us. When Ryan was almost one Jess left." Rory said sadly. "I got a letter from him about six months later. He said he was trying to get his life together and had started working at a small book publishing company in Philadelphia. He gave me an address and phone number to contact him, but I never did. I was still pretty upset with Jess at the time, so I just put the letter away and haven't looked at it since. I want Ryan to know his Dad, but I don't know how ok I am with it. If Jess really does have his life together, I'd be willing to give him a chance with Ryan, but he has to be committed to being a permanent part of Ryan's life. I can't do the in and out thing."

"You want to get back together with Ryan's father?"

"No. Not at all. I just want to make sure he's going to be around for Ryan." Rory clarified. "I just want everything to be ok for Ryan. I work so many hours so he can have a good life, but I feel so guilty about leaving him with friends all the time. I wish I could spend more time with him, but it's just not a possibility right now."

"Ok. Is that everything that you wanted to talk about? Is there anything else that's stressing you out or bothering you?" Meg asked politely.

"It's just everything. Nothing is turning out like I planned. I didn't ask for this life." Rory admitted. "I just wish everything was different and I could go back and make different decisions."

"I hate to disappoint you Rory, but I don't have a time machine." Meg joked.

"I know." Rory responded. "I also know that if I want to change my life I have to take the first step. That's the part that I'm having trouble with. I pick up the phone at least once a week to call my Mom, but I can't do it. I want Ryan to know his family. I don't want to raise him in the city. What I really want is to move back to Stars Hollow and raise Ryan there. The problem is that I can't seem to do it."

"Contacting your Mother after nine years of silence and the father of your child after eight is a challenge. Have you thought about what the first step would be and when you would make it?"

"I've picked up the phone once a week for the last five years to call my Mom." Rory said plainly. "Jess is a bit more complicated. I don't think I'll be able to talk to him on the phone without screaming, so a letter might be better option there."

"Yes that would be better." Meg agreed. "Unfortunately, we're running out of time in our session. We've talked about lots of things today. I have something I'd like you to do before we meet again. I'd like you to make a list of your feelings; one list for your Mother and one for Jess. Just keep a small note pad with you and write things down as they come up. We'll go over it next week and discuss things further."

"Ok. I'll see you next week." Rory said before standing up and shaking Meg's hand. She excused herself from the office and quickly exited the building.

Rory walked out of the building Meg's office was in and pulled a pack of cigarettes out of her purse. She quickly took one out of the package, put the pack back in her purse, and lit the cigarette. She silently cursed herself as she exhaled. Ryan kept asking her to quit, but she hadn't been able to take the first step yet.

Rory walked quickly toward the nearest subway stop and tried to slow her brain down. Her lack of action to change her life had been a point of frustration for her for years and it had finally come to a head. Besides the smoking habit, Rory had recently taken to drinking more frequently. She told herself that she was fine and never let things get out of control in front of Ryan, but she had been too far gone to pick him up from her best friend Julia's house a few times. Julia was kind enough to look after Ryan several times a week, but she drew the line at watching Rory throw her life away. So, Julia confronted her one day and suggested she go see Meg Alder for some counseling. If it wasn't for Ryan, Rory wouldn't have listened to Julia and continued to spiral out of control. However, Rory couldn't bear to hurt Ryan anymore, so she vowed to fix things and do what was best for Ryan even if she wasn't comfortable with the idea.

About twenty minutes later Rory walked to her apartment door and opened the door to find Ryan sitting at the table working on his homework while Julia read a book on the couch. "Hi guys." Rory said as she closed the door.

"Hi Mom." Ryan said while continuing to work on his homework.

"Hey Rory." Julia said and stood up to give Rory a hug. "How did it go?" She asked quietly.

"I think it was good. I did the majority of the talking." Rory said. "Are you sure this is going to be helpful?"

"It's as helpful as you let it be." Julia said. "I hate to cut this short, but I need to get going. See you tomorrow?"

"Yeah. Thanks."

"Bye Ryan." Julia said before leaving as he waved to her.

"So how was your day bud?" Rory asked while walking over to the table to examine Ryan's homework.

"School was boring as usual. What are we having for dinner?" Ryan asked.

"Pizza or Pasta?"

"Pizza." Ryan answered quickly.

"Ok, I'll call it in."