You and Dean were in an on-off relationship; you'd known eachother since you two and Sam were kids- you all practically grew up together since Sam and Deans dad was close with your dad. You'd since joined them on their hunts.

The reason you and Dean always got together and then broke it off again was because the pair of you were too alike for your own good; you both constantly argued. Though, it didn't mean dean didn't still love you.

You were investigating some haunted apartment building; you and dean were currently broken up, so you tried to go with Sam instead during the investigation, but dean protested. So, you- with your arms folded and your expression stubborn- were stuck with dean as he protectively stood close to you, his eyes narrowed as he held a flashlight, looking for any signs of a spirit.