A/N: Welcome to my first steps into the Gilmore Girls fandom. Please be kind as I have never written for this fandom before, but it one that I love dearly and have been a fan of for a very long time.

Disclaimer: I own nothing except the plot of this thought process. Everything else belongs to the mind of Amy Sherman-Palladino.

This was written for the 31 days of Fanfiction Challenge day 6 which was a fandom that you love, but have never written for. I have written a crossover for this fandom, but never anything solely for this fandom. I am a hard core Rogan shipper if you couldn't tell.

Thank you to xxDustNight88 for the beta work of this story and tell me that it doesn't completely suck. I trust you with my life. All the love 3

If you are interested in checking out my other works or keeping up with me in general, I have an author's page on Facebook that you can check out (starrnobella Fanfiction) as well as a group (starrnobella Fanfiction Friends & Fans) that I am very active in on a daily basis. I'm also on tumblr (starrnobella) that you can follow along with me as well.

If you enjoy it and would like to see me write more of this fandom, please leave me a review!

Love always,
~starr

Her life had become an adventure ever since he walked into her life. There was no denying that. She had done things that she would have never imagined doing. Things that she would do again in a heartbeat if she was ever given the chance.

She followed him into the unknown world of the Life and Death Brigade where her eyes were opened to new experiences that she never imagined. She had jumped off a tower attached to nothing more than a bungee cord and an umbrella to catch her fall. That jump was the first leap into a relationship full of life.

She attended and threw the craziest of parties with and for him. Parties that would rival her own mother's in the insanity that would transpire as the night went on. Parties that would make her mother proud.

She also had some of the most eye opening experiences in his presence. Because of him, she was one of the most successful Yale Daily News editors and was able to put out an edition of the paper that was still talked about to this day. He helped her make it all possible.

She even stole a boat with the man who was standing in front of her waiting for an answer. He was willing to go to jail with her because she had a bad day, and yet when he asked her that simple question, she froze.

So why was she hesitating? Honestly, she wasn't sure.

Rory Gilmore had only loved three men in her entire life. The three of them couldn't have been more different if they tried. But that didn't stop her from loving them.

Dean was the first. Her first love. First kiss. First slow dance. Her first everything. He was the high school sweetheart that every girl dreamed of having. Dean was willing to do anything for her and she was willing to do anything for him. To quote her mother, he was the perfect first love, but she was spoiled with him.

Her relationship with Dean showed her the things that were missing from her life. Things that she was able to find with someone else when the pair had finally grown apart. No matter how long it took them. However, Dean would always be her first and for that he would hold a special place in her heart.

After Dean was Jess, and Jess was the bad boy. The one that every father dreads, or in Rory's case, her mother dreads. He showed her a different side of him than he showed to the rest of the world. A side that cared. The side that proved he wasn't the neighborhood bad boy that everyone was convinced he was.

Jess showed her that she didn't always have to live life by the book and that it was okay to go a little crazy every once in awhile. He was also the one to show her how much it hurt to never get to say goodbye. Sure, the pair had become friends again in recent years, but there was still a part of her that would never forgive him for leaving. Especially when she needed him the most. But he too would always hold a special place in her heart, no matter what decision she made now.

Then there was Logan. The preppy rich kid that she strove never to be after Christopher had given her that money. He was the type of guy that she hated when she was in Chilton. If she was being honest with herself, he reminded her an awful lot of Tristan the longer she thought about it.

She had every single reason in the whole wide world to say no to his proposal. He had proven himself to be a butt-faced miscreant on numerous occasions. Deep down she was still hurt by the fact that he had slept with half of Honor's bridal party, but at the same time, she could understand the misunderstanding. It wasn't something that they had really talked about, she had just left.

Not talking about things until their emotions exploded was kind of their thing. But no matter what they fought about, the two of them were always able to work it out. Some way, somehow things always got better from where they were.

Logan was the king of big gestures. Fights, apologies, romance, and anything else he could think of was done in a big way that everyone would remember it. It's probably why he was a leader with the Life and Death Brigade.

His proposal had proven to be no different. He had planned out every last detail down to the finite details of what would happen after he slipped the ring on her finger when she said yes. He had even found a job for her for after graduation in California. He knew her better than she even knew herself at times. All he needed was for her to say that one little word. But instead, she didn't say anything.

And now, here she was sitting in her empty apartment staring at the most beautiful engagement ring she had ever seen, contemplating her answer. The words of his proposal playing over and over again in her mind. The fact that he had taken the time to ask Lorelai's permission to propose took a lot of courage. Her mother wasn't exactly Logan's biggest supporter, but she would never stand in the way of her happiness.

She loved him. Her hesitation to answer him wasn't because she didn't love him. In fact, the more she thought about it, the more she started to realize that she loved him more than she had before. She was even able to picture her life in California with him. Everything that she saw in her mind made her happy.

So why didn't she just say yes when he asked?

Did she question his love for her? No. He had proven it to her a million times over since their last break up. Even when he was in London he found little ways to show her how much she meant to him and his love for her. The things he did for her meant more to her than he would ever be able to understand.

The longer she stared at the ring, an answer to her own question was finally able to rise to the surface. Every big decision in her life she talked about with her mother. Except this time, Lorelai wouldn't tell her what to say.

"I can't help you make this decision."

Those simple words kept playing in her head. She knew her mom was right, but it didn't feel right making such a life changing decision without her input.

Rory opened the box and pulled the ring out. Placing it between her pointer finger and thumb, she sighed as she allowed the light to reflect off the facets of the stone for a few moments. She took a deep breath and slipped the ring onto her finger.

It fit perfectly and looked as though it was meant for her. He really had picked this ring out with her in mind. As the light caught her eyes again, she smiled and pulled her phone out of her pocket.

She sent a quick message off to Logan asking him to come by her apartment later that evening and then dialed her mother.

Lorelai answered on the second ring. "Hello sweet child of mine!"

"I'm saying yes."