Supernatural Imagines (On Hiatus)

It's Complicated-Dean Winchester

Y/N/N= Your nickname

Dean Winchester, the man you loved to see and hated to go. Also one of the more complicated and complex subjects in your life.

Dean and you weren't together or anything but you were definitely more than just friends. Maybe friends with benefits...? You just weren't sure.

Dean and you met when you were teenagers with you only being a year younger than Dean. Your dad was a hunter and you met Dean when your dad and his teamed up on a wendigo hunt. The two of you quickly became close friends, the best you and Dean have ever had before. Since you both always moved from school to school too quickly to gain friends. You guys stayed in contact after the hunt finished. The two of you called each other whenever you or Dean got a chance. Unlike Dean though, you gave up the hunting life when you got older.

Your father had finally gotten his revenge on the vampire that killed your mother and your sister. Devastatingly, your father decided to do one last hunt afterward which was the one that ended up killing him. You were eighteen at the time and had just finished high school.

Dean showed up at the funeral with John and Sam accompanying him. Mainly they were here because Dean begged John, who wasn't big on attending hunter gatherings even if they were funerals.

You stood near the duffled up body, prepared to be burned, alone after Bobby Singer was pulled away from you by a group of hunters.

Dean quickly made a beeline for you knowing his father wouldn't let him stay long so he didn't want to waste a second.

"Hey, Y/N." said Dean softly as he walked up to you

"Dean." You got out as you now face him with surprise swirling in your teary eyes

"I'm sorry about your dad." said Dean as he pulled you into a tight hug

You nodded softly then not sure what to say even though that had to be the hundredth time someone has said that to you in the past hour. Your arms moved you wrap around Dean's torso as your head moved to rest on Dean's chest.

The two of you stayed that way for a little. Dean's arms providing you with comfort that you didn't know was mutual. Dean was soaking in the feeling of your arms around his, the contact providing him with a temporary feeling of happiness and comfort. He knew once the two of you parted way those feelings would disappear which made a small pang hit his heart.

Even though the two of you didn't want too, the two of you moved apart.

"So what are planning on doing now?" asked Dean genuinely curious

If you planned on hunting down the beast that got away after he killed your father, Dean wanted to go with you. He wasn't going to let you go hunt that thing alone.

You bite the bottom of your lip slightly at his question. You knew what he was really asking but you didn't plan on going after that monster...or any monster really.

"I'm actually thinking about going to college." You said after a few seconds of silence

Your words made Dean tense slightly.

"I just-I lost so much because of the supernatural and I feel like hunting will only hurt me. Make me constantly think of anyone I already lost. I just feel like this is the better option for me." You added with a slight nervousness in your voice

Dean nodded slowly but the hurt and pain swirling in his green eyes showed his feelings. He didn't know when you meant giving up hunting if you meant giving up on him as well. That if this was your way of telling him that you guys couldn't be friends anymore.