Dean

When Dean first said "I love you." It was when you both just came from a hunt, and you almost gotten killed by the demon. You got patched up by Sam and Cas helped heal your wounds. You were grateful for them and you were grateful for Dean. It was almost like you weren't surprised when he said it.

Moment:

"Alright (Y/n), I am going to heal some of the wounds now." Cas said.

You nodded in pain and waited for the pain to go away. The four of you were currently in the Impala with Dean at the wheel and Sam, Cas, and you in the back. You had gotten very hurt on the demon hunt. The demon a taken a special liking into hurting you. You had bruises and cuts and a pounding headache that wouldn't go away. When the Impala drove into the parking spot in front of the bunker, you tried to get out but you were too weak. Dean ran around the car and picked you up bridal style.

"Dean put me down." You said sternly.

He put you down with a confused look on his face. You limped towards his back and tried to jump on it. Dean grabbed your legs and continued to give you a piggy-back ride until he reached your shared bedroom. He lay you down on the bed and sat next to you.

"(Y/n), you had me worried today." Dean said softly.

"Oh please." You said. "I have you worried every day."

"I love you." Dean said suddenly.

You had a shocked look on your face but it was soon replaced with a smile.

"I know." You said.

"You sound like Charlie." Dean said laughing and shaking his head.

"I know."

Sam

When Sam first said "I love you" it was during your third date. Your third date with Sam was a walk in the park. Literally. It was at the town park and it was under the moonlight. You were holding hands and just taking a stroll until he stopped and blurted it out.

Moment

The stars were lighting up the sky and it made the lake next to us light up. Your fingers were intertwined with Sam's and you both were walking down the rocky path to get to the car again. It was your third date and Sam had decided to take you for a walk in the park. It wasn't extravagant but it was special. You and Sam had reached a park bench and you both sat down. You were looking at the stars while Sam had been looking at something different. He had been looking at you. You turned to look at him and saw him staring. It was sort of cute in a way.

You looked away and blushed. Sam took your hand and was still staring at you.

"I love you (Y/n)." He said suddenly.

You smiled and looked at him again.

"You know that I love you right?" Sam asked.

You nodded and simply pressed your lips against his.

Castiel

When Castiel had said "I love you.", it was out of the ordinary but you wouldn't expect anything else from your Cas.

Moment

You were sitting in the main library area of the bunker reading up on some lore. Sam and dean were out on a hunt and Cas was no where to be seen. You closed the book after about an hour or so and stretched out your arms. Your eyes slowly shut and you drifted to sleep.

You woke up with Castiel staring at you. You jumped and started heavily breathing.

"Cas, you can't fricking wake me up like that, what the hell." You said.

Cas looked at you and slightly tilted his head.

"I love you (Y/n)." Cas said.

You nodded and fell back asleep with a smile formed on your lips.