3 times, 4 times

There you sat in the impala, outside Sam's dorm at Stanford. Dean sat next to you. You were both nervous, he tried not to let it show at first but he knew he couldn't hide it from you. You were his best friend and had been for years. You met when you were younger. When they first started staying with Bobby when John left for hunting trips. You had all become extremely close especially you and Sam. It was easy to tell that you both had developed feelings for each other. The only one you ever admitted it to was Dean. Him being your best friend you confided in him about a lot of things. 

Now here you were years later sitting in the impala with him . John had disappeared and you were looking for him but you needed Sam. You had both decided to go get him and it was all very anxiety inducing. 

Dean held your hand tightly and took a deep breath you rubbed the back of his hand with your thumb in a soothing manner. Trying to calm him and yourself down. 
"It's ok Dean, we can do this. It's just Sammy... everything will be ok." You spoke gently to him. Reassurance seeping from your words for him and for you. 
"I'm not sure (y/n), what if he doesn't want to see me. What if he tells me to get lost... or get dead... Im scared." He confided in you. You could see his eyes glisten with unscheduled tears as he ran his free hand over his face. "It will all be ok Dean. He's your brother, he loves you. C'mon I'll be right beside you." You told him. Trying to be strong for his sake. 
He looked at you, he knew you all too well. He could see just how scared you were, he knew you were trying to stay strong for him. He gave your hand a squeeze of reassurance. "Ok... let's go." He said with a deep breath. 
Letting go of your hand he got out of the car and so did you. 
As you walked to the door his hand was at the small of your back, it was always something he did to comfort you when you were nervous. 

Dean swiftly picked the lock and walked in, you followed behind him quietly. Your eyes adjusted to the dark room quite easily seeing as they've had to do so many times before while on hunts. You had been looking around, when you heard Dean make a noise. Then in a moment of slight commotion Sam came at Dean. Dean pinned him to the ground and you let out a quiet laugh. 
Sam's head whips around to look at you. You give him a small smile, not exactly genuine seeing as you were still scared of the outcome of your visit. 
"(Y/n)..." he trailed off. Dean helped him up off of the floor and he took a step towards you. "Sam." You respond. You gave him a nod and turned your head to look at the floor. 
All of a sudden the light got flipped on and in the doorway stood a beautiful blond girl. She was wearing just a shorter shirt and underwear. Your cheeks flushed when you looked at her. It was a weird position for you seeing as she was obviously living with Sam.Seconds later she was said to be his girlfriend, your heart broke just a bit.. Dean saw this and went to grab your hand, he gave it a squeeze of reassurance letting you know he was there for you. Staying strong you got through introductions and Dean began to explain the nature of your visit.
"Dad's on a hunting trip and he hasn't been home in a few days." Dean said. Sam politely told Jessica that he needed to talk to you alone. She kindly agreed and turned to walk away. Being polite you wished her a goodnight and she did the same. 

You all walked down the stairs. "We need your help Sam, so you're either in or out. If you're out then I won't force you. You can forget all about us and move on with your elite Stanford life with your beautiful girlfriend." You stated. Your voice was cold and eerily calm while speaking to him, despite the hurt, anger, and anxiety rushing through you. 

He looked at you with wide eyes.  Dean knew you loved him so he understood why you snapped. He was upset at his brother too. 

His shocked face turned hard his jaw clenched and his eyes were stern. 
"You really think I would forget you? You think my life is elite?" He questioned you. "Yeah Sam, I do suppose you would forget us seeing as the surprise on your face when you realized it was us. You didn't contact any of us the whole entire time you were gone. So forgive me for thinking you could ever possibly forget us." You bit back at him. 
Hr just stared at you, so you continued. 

"And yeah I do think your life is 'elite'. Going to Stanford studying Law having a beautiful girlfriend. Getting to leave every monster, every demon, every night you hoped your family would come back alive, behind. You found a love that is really something, not just some daydream. You know what I have when I go to sleep at night. I have 4 hours of shut eye at the most. My head filled with the screams and fear of the people I couldn't save; and you Sam. The night you left. Left your brother, your father, the girl who loved you no matter what. Left me alone with nothing to hold on to. Sure I have Dean, and I love him with everything in me, but he's not you. He isn't the one I had my first kiss with, the one who showed me that being alone wasn't ever being alone because I knew you were thinking of me like I was you. Now I am alone because I know for a fact that you have never given me a thought when I have spent hours of thinking on you." You breathed out. Your voice got weaker over time but it never wavered. 

Dean stood by your side as always ready to defend you. 
None of this came as a surprise to Dean, seeing as you have told him everything since you were little. It just hurt him to see you finally get to speak your mind to Sam. 

"(Y/n), I'm sorry... I didn't know, I didn't know you felt that way. I do think of you, all the time. You're my best friend." He said to you, taking a hesitant step forward. 

Your heart broke even more at his words. "His best friend" you thought. 
You took a step back. "You can come with us if you want to." You said completely dropping the conversation not wanting to embarrasse yourself anymore. 

You walked away and got into the front seat. You could feel him watch you, and it made you almost nervous. You weren't expecting to confess all of that in that moment. Your heart was racing and tears stung your eyes. 
Your eyes were trained on your hands that were resting in your lap. 

Before you knew it Sam was sitting in the back seat, and Dean was driving off. Dean reached over to grab your hand and held it tightly. You squeezed his hand 3 times for comfort. He squeezed it back 4 times letting you know he was there for you. It was the little tradition you had when either of you didn't want to speak.  You gave Dean a small smile and he did the same. 
Sam witnessed this and for some reason it made his stomach turn. 

Little did either of you know but Dean had fallen in love with you over time even before Sam left.