Disclaimer: I do not own Gilmore Girls or the lyrics I will place in my chapters.

Synopsis: Take place during season 2, Dean and Rory are having trouble because Rory has her eye on someone else other than Dean. Jess has stepped into the picture. The night when Lorelai leaves for her weekend get away with Emily. Rory lets Dean come over and gets pressured into have sex for the first time. And now 16 year old Rory finds herself pregnant. While Luke is realizing his love for Lorelai is less platonic and more romantic. What will happen between Luke and Lorelai? How will Lorelai respond knowing history repeating itself? and Lastly what will come of Rory and her love complicated love life...

Authors Note: I'm writing this story different than the other I've done before. This will be from different points of views from the main characters such as Lorelai, Rory, Luke, Jess and Dean. I'm a huge literati fan but I dont know I may surprise you. I'm not guaranteeing Dean and Rory end up together nor that Jess and Rory will not. Maybe she'll be single, you just need to begin reading and join me on a different version beginning in the middle of season 2. I can guarantee java junkie because I love Luke and Lorelai. Don't forget to follow, favorite, and review. I've had this idea for over a month now, so hope it comes out exactly how I want it to. I apologize that it is so long. You may watch the trailer for this fan fiction, by clicking my username and going to my profile. Anyways Enjoy!(:

Chapter One: Say Something

And I will stumble and fall.
I'm still learning to love
Just starting to crawl.

Rory's Point of View…

I'm listening to Dean yell at me and all I can think of is how I ended up in this situation again. Paris wasn't supposed to show up and she wasn't supposed to leave and have Jess show up. I should've begged Paris to stay, but I didn't. I guess I wanted to prove to myself that I could be alone with Jess. That I wouldn't get an urge to kiss him, but I always do. Then I hear Dean say "You totally lied to me!"

And all I can say is "I didn't." Because it the truth, I didn't invite Jess over, so that means I'm not lying right?

"Turn the situation around Rory! How's it looking?"

"It's looking complicated and I'm trying to explain it to you"

"Ugh that crap" his voice sounds low. He looks defeated like he let out all of the steam he had been holding in. I feel guilty, I feel awful. I love him. I do. I just don't know if I am in love with him anymore. The butterflies are losing their wings little by little. This is all Jess's fault. Jess…I mean Dean is my boyfriend forever. I love him, he is good to me, and he is it for me. I want to reach my hand over to his cheek to feel his hair droop but he still looks angry. Then he scoffs and says "What are you trying to explain? You've been into him since he got into town"

My eyes shuffle from his face to the floor. How did we end up in my room we've never been here alone…together. That made me nervous; my palms began to sweat as my cheeks turned hot "No I love you"

"You love me?" He asks me in disbelief and I did…I mean I do…was I attempting to convince him or myself… "Yes I love you" I protest. He clenches his jaw looking in my eyes, like it's hard for him to believe me. He reaches over grabbing my hands, our fingers intertwined as he reaches closer to me. His lips meet mine, I feel safe. I feel that the yelling is over; the walls have stopped caving in. And now my heart is beating as he lays me down on my bed. As he starts kissing my neck, I know where it's leading. I just don't know if I should stop him. "Dean" I say as he is kissing my neck. "I...we...can't." He stops and stares at my face "You wouldn't stop me if you loved me..." Was he right? If I loved him this would happen eventually. But at sixteen my mom got pregnant at sixteen. I felt his eyes stare into me while his hair flopped onto his face. He looked the cutest like that. I leaned in giving him a kiss finally letting his hand in my shirt.

I didn't know where to go; I didn't know who to talk to. Here I am standing outside of Mrs. Kim's Antique waiting for Lane. I see my best friend come out from the door "Do you wanna come in?" she asks. I shake my head, feeling Mrs. Kim would know, I feel like everyone knows. It's like a monsters eating inside me, not being able to tell my mom. I know she'll be coming home soon and the thought of facing her. The thought of telling I lost my virginity felt harder than every test Chilton has given me. I mean I don't have to tell her. Normal daughters keep everything from their mothers. Like Lane, she would be the only one that would be able to make me feel better about not telling my mom. She is the queen of hiding stuff from her mom. I hear her say "Rory are you okay?" I guess I hadn't noticed I was pacing back and forth and thinking and not speaking. So many words that I don't know how to explain, "Yes…I mean no… can we go to the gazebo?" She gives me a warm smile like she is trying not to upset me and says "Yeah, let's go." Do I look like a ticking time bomb on the outside as I feel on the inside, are my feeling that apparent? We reach the gazebo in silence when I finally say "I slept with Dean" She sits down on the bench saying "You what?" she looks shocked, maybe I should've told her to sit down first "I slept with Dean in my room last night in my bed"

"Oh my god!" She covers her mouth with fingers seeming as afraid as I am to be talking about this and I replied "I know. Who would have even thought Dean could fit in my bed. I mean, it's so small and he's not small. He's tall, not small. Great. I'm rhyming." I'm pacing back and forth as I speak, I watch Lane pat the seat with her hand saying "Sit down" I listen trying to calm my beating heart, I can feel every touch vibrating through my skin. Then she grabs my hand and says "I'm sorry, I just have to ask you" she takes a breath and begins to whisper "How was it?"

"Why are you whispering?" I ask not understanding the sudden change of tone.

She continues to whisper "Because I just think no matter where she is, my mom can hear this conversation"

I match her whisper "It was a little scary" and it was. I wasn't mentally prepared for it…actually I didn't feel prepared for sex at all.

"Was he nice to you?" my best friend asks with a smile.

"Yeah. It was…" I smile trying not to blush "I mean he loves me" my smile fades remembering the reason I came to talk to her "I think I did something that - what do you think?"

"Of what?"

"Of what I did. I need some perspective."

"From me?"

"Yes."

"You need some perspective on sex from me?"

I feel like I'm begging her. "I need some perspective on sex with Dean from you."

"Oh, well, Dean loves you." She smiles

"I know." I smile back at her.

"And you love him."

My smile fades feeling like I'm lying to myself and her; and say "I know."

"So it seems like -."

My smile drops and I look at the floor, ashamed. "I'm sixteen"

"I know" her gaze follows the same spot on the floor.

"How did I overlook that? I'm sixteen and I lost my virginity without even protesting. Without even paying attention about condom usage. That's the first thing you're supposed to ask right?" I place my hands on on my forehead, feeling the stress being overwhelming.

"Well you can ask now"

"It's too late to ask now the deed has been done"

"Maybe you should talk to Lorelai."

"No." I say in an instant. No way, was I ever mentioning to my mom.

"But she already knows about you guys."

"She knows about our relationship not our sex".

"She's better than me at this sort of thing because she at least has a frame of reference."

"Talking to her is not an option."

"Okay, well, then –"She gets interrupted by Mrs. Kim walking towards us. Had she been standing there long? Maybe Lane was right about her powers and she did hear the words sex escape our mouths. Lane says "Mama?"

"Lane it's time to come home"

"Yes Mama" she looks at me one last time, waving goodbye. As much as I wanted my talk with Lane to make me feel better. I didn't feel good at all. My gaze does a circle around town ending at Luke's watching Jess serving a customer and all I can think was, Jess and I could never be together not after this.

I'll be the one, if you want me to.
Anywhere, I would've followed you.

Luke's Point of View…

It had been months since Rachel left and I hadn't forgotten the words she had said. The sadness in her eyes as she opened the door and turned back to say "Don't wait too long?" and I stared back confused "To what?" and she said pointed blankly "To tell her." It was then that I began to open my eyes and think how does Lorelai always end up on my mind? In my conversations? In my moods? She mattered so much to me. Yet she was just a friend…right? I watched her walking the square towards the diner. She was beautiful and could carry on a decent conversation. Seemed like the sanest person in the room besides me most of the time. But she was Lorelai…

I remember meeting her for the first time carrying a baby seat and walking in here saying "I have tried every coffee place and cannot find a decent one in this town. Please tell me you've build your place around your coffee making skills" I heard everything she said, noticing she was new in town. She had beautiful bright eyes matching her light skin and contrasting with her dark hair. And all I could say was "Wait your turn." She then placed her baby seat on the counter and I said "You can't have that up here" She takes out a newspaper ignoring my request "Whens your birthday?" I looked at her lost; I didn't understand why she wanted coffee when her mind seemed to run 1000 miles per minute. She kept talking about horoscopes, reading every single one on the damn newspaper and I finally budged and said "November 7." I see her from the corner of my eye write something down and rip a piece of paper. I stare at it on the palm of my hand and it said "Scorpio You will meet an annoying woman today give her coffee and she will go away" I gave a half smile and gave her coffee. While she continued with saying to keep in my wallet because one day it would bring me good luck.

I never was an expert at the dating game and when I wanted to maybe try to make it to something more. She was seeing someone and then she would show up at the diner, crushed and broken hearted yet again. This turned into her sanctuary and I turned into her psychiatrist, her friend, her confidante. So I waited for the right time. Pushing my feelings aside, shoving them in a dark place and waiting for the right time. Was now it? My thoughts get interrupted by the bell on the door ringing; she was inside walking towards the counter. "Luke. I need a deep coffee cup to erase this weekend with my mother." I nod and turn towards the coffee. I say "It couldn't have been that bad" as I poor her coffee, she looks sad and defeated. She takes a sip of her coffee "Trust me. It was a reminder that my mother and I could never be friends. I will always be her disappointment and she will be my annoyance." And then I say "I'm sorry to hear that." She practically spits out her coffee in shock of my sincerity and says "You are?" Oh no I've showed my feelings yet again. This always slips out. I have to remain grumpy and indifferent. I remember the day she was sad about the Christmas party her parents didn't invite her to and I had said "Will you marry me?" and she said "What?" in that same shock face I am staring at now. I could shake off what I said or I can finally say something. I reach over to the platter of donuts and pick out Danish. She says "Luke? Have you gone mental? It isn't Danish day and your showing feelings" I try not to crack a smile at her wit and I say "Actually Lorelai" I finally look up at her and with her mouth full of Danish she says "Yes?" I take a gulp and say "Do you wanna go to a movie this Sunday?" "A movie?" she inquires. "Yes you watch those." Why does she always have to make things so difficult? "Yes I watch those, you watch baseball but I guess you do need a moveducation" She smiles, I love seeing her smile. "Good, see you around seven" She looks like she is waiting for me to break out of character and say I'm kidding then I see through her smile say "Okay." I walk towards the other customers to serve them. Hoping she doesn't change her mind.

And I am feeling so small.
It was over my head
I know nothing at all.

Rory's Point of View…

I was late, I stared at my planner. I hadn't noticed, pretending to be cool with my mother was hard enough. I had been feeling nauseous do signs show up this early? I didn't want to risk it and went to a store in Hartford buying a pregnancy test. Well a box that came with three tests. One could be unreliable; I took them before my mother came home. As I waited for the tests I thought about having to face my mom or my grandparents or my dad. They would all be disappointment. I would be exactly what everyone expected. I realized I haven't talked to Dean, he went to visit his grandma in Chicago and I…just couldn't deal with him freaking out. I can be the only one doing the freak out. I almost shivered at the sound of my watch ringing, my timer has finished. I turn off the alarm and watch over the tests there was two pink lines. I read over the boxes making sure I wasn't mixing up what I thought those lines meant. I wasn't…I'm pregnant. Oh my god I'm pregnant. I gather up the tests and walk downstairs to my room. I don't want to cry, I don't want to crack. It happened. I was dreading this the whole week. I hear the door open and hurry in placing the tests under my bed. My mother walks in my room "Today is the night and I have no idea what to wear. Do you think if I wear plaid, he'll think I'm making fun of him?" I fake a smile and say "Yeah I think so" I say trying to make a smile, trying not to cry. I can't tell her right now. She is happy, she is about to go on a date well with Luke nonetheless but a date. My mom asks "Are you okay?" she can see right through me, I hate that. "Yeah, I'm stressing about this project actually I forgot some supplies, so I will be back" I start walking out and she says "What about my date?" I think these might be the last moments she would smile at me like I'm the best person and I say "It's not with me." And I walk out.

I walk towards the bridge. I need to think. I need to clear my head. I feel like this huge weight is on me and I'm not even fat yet. As I sit on the bridge looking at the water, watching my reflection, watching the tears fall into the water. I can't help but remember that I read in a book once if you begin crying with your left eye it means you're in pain and if it's your right eye you're happy. I wish I would've begun crying for my right eye, I wonder how my mom felt when she found out she was pregnant at sixteen. Did she feel this sick at the thought of me? I'm crying for the future that I don't know will happen, I'm crying at knowing I've disappointed the people I love but mostly I'm crying at where I'm sitting. Here is where I sat and laughed about books with Jess. Why did I care what Jess thought, but I did. I did care. I hear the bridge creek, now I remember I'm in his favorite place in town, did I not think he would show up. And now I'm crying in front of him before he gets any closer I say it out loud for the first time "I'm pregnant," he stood there just staring at me wipe the tears off my eyes. "And the sad part is, I didn't even have sex for love. I had sex to prove I wasn't into you. To prove that a part of me still cared for Dean and now I sit here with his baby and all I can think is how you'll hate me and you'll never like me. Guess that proves I like you right?" I finally look up to stare at him and I watch him take one last look at me and walk away.

And I will swallow my pride.
You're the one that I love
And I'm saying goodbye.

NEXT CHAPTER:

They keep me thinking that we almost had it all
The scars of your love, they leave me breathless
I can't help feeling
We could have had it all

I hear my mother say "So, this is all my fault? I set one crappy example for you, and you have no choice but to follow in my footsteps?" I begin to walk away, tired of arguing and she continues to follow behind me saying "Rory, what are you going to do now? Huh? Is there a plan?"