A/N: This is a set of 7 short drabbles that I wrote about all of the times in his life that Sam has felt heartbroken. Written for a lj drabble challenge. This is a one-shot and will not be continued. Please read and review! Thanks so much!


1. Target Practice

Eight years old. Despite spending his nights with a BB gun shooting soup cans off fence posts, Sam still had yet to find his strength without the heavy artillery. Dean panicked when he couldn't find his kid brother. Until…

Ping. Ping. Ping.

Sniffles. Crying. That's when Dean rounded the corner; saw Sam pointing and shooting over and over. "Hey kiddo," he cooed, ruffling the younger boy's hair. Dean ignored the tears. Sam ignored Dean.

The elder boy's eyes fell on Sam's target practice. A flyer announcing their school's Mother-Son dinner. Dean couldn't keep from pulling Sam into a tight hug.


2. Crush

"Do you even know her name?" Sam growled, angrily. It wasn't uncommon for his teenage hormones to get the better of him. And it wasn't the first time he had caught Dean in bed with a girl in their dank, musty motel rooms. But it was the first time Sam had recognized the girl; knew her, wanted her for himself. Dean's answer was some gibberish combination of several girls' names. Sadness. Humiliating pain. Sam had heard the juxtaposition of the crush. But this was what it felt like? Ache. Longing. Desire. All for the girl in Dean's bed named Allison.


3. History Repeating

He never expects history to repeat itself. Not like this. Not with her.

She is his light, his life, his all. Jessica is everything that his life had been missing.

And now twenty-three years later, he is his father incarnate.

Anguish. Agony. Sorrow. There's no way to describe the loss when she meant more to him then breathing, more than his own heartbeat. His fire began the moment Azazel's was extinguished; when Sam realized Azazel was tempting him, baiting him, pushing him. He was breaking Sam, forcing him, threatening him. And now, twenty-three years later he is his father incarnate.


4. Time of Death

Coffee cup hits the floor seeing that his father is already down there. It's beyond more than Sam can stand, almost losing his brother and then seeing his father like this all in the same day. Help. He yells, screams for someone to help. He and Dean watch in horror. "Time of death…" He can't hear the rest. He won't allow himself to hear the rest. His father- torn out from under him like a rug in those stupid cartoons he watched as a kid. Tears stream hot down his face and he doesn't even try to stop them anymore.


5. Trigger

He hadn't expected to feel something for her so quickly. But then, it had been so long since he had felt anything he couldn't remember what he should do. Something told him putting a bullet through her heart was on the 'don't' list. She asked, begged him to pull the trigger. And as Dean dropped the gun into his hand he could feel the fresh gashes on his heart.

"Just wait here," was his only plea. What shook him most was the way she looked at him before the shot rang out, shattering Sam's very core. The look of love.


6. Save You

The blood and carnage is more than he can bear, especially because it's his brother's body laying there. Everything he had done to save the one person in his life that he could always count on, good or bad, and yet there he was in a pool of blood. He had tried everything to save Dean even when everyone told him that it couldn't be done. Sobs, deep and heartfelt erupted from his chest as he pulled Dean's head into his lap. "I'm sorry," he choked out. "I couldn't save you Dean- So sorry I couldn't save you from this."


7. Evil

Satisfaction. The feeling of driving the knife straight through Lilith. She'd caused far too many problems for him these last several months. Long, tiring, stressful months at war with his brother; at war with heaven and hell alike.

Ruby's eyes glowing; basking and sharing his satisfaction. But then why does she look so… evil? And her words, swirling in his head like some god-forsaken tornado burying itself in his skull. Anger. Resentment. Disgust. She had played him. Understanding. Horror. Heartbreak. He had broken the last seal; raised Lucifer. Dean forces the knife in. It is done. But the heartbreak remains.


A/N: Thanks for stopping by. Please let me know what you think?