You are an old hookup of Dean Winchester. You met at a bar, talked for a while, and made a connection. As you spoke, Dean didn't realize he was falling for you. You went home together. Usually, Dean would leave without saying goodbye after spending the night with a women. But he decided to stay for a while. But as soon as there was a new case, a djinn in the woods, Dean took off. You hadn't seen him for six years, after that. While he was away, Dean and his little brother, Sam, were fighting demons, angels, archangels, and lucifer. To say there were busy, is a stretch.
Dean spent a year with you and your son, Ben, after Sam went to hell. It's been a year since Dean joined your and Ben's small family, and it couldn't be better. But everything fell apart when Sam came back from the dead, showing up at your house to save Dean from djinn that broke in. Dean tried to make it work. He tried to hunt, but also stay in your and Ben's family. But it didn't work out. And you broke up with Dean.
It's been a few months since you and Dean split up, and you've been on a few dates- trying and failing to get over him. Ben hated seeing you go on so many failed dates. He called Dean over and over again using your phone. He had been ignoring the calls, assuming that it was you calling- which it was a few times. When he did answer, Ben lied and said you were really sick. Although Dean was in the middle of an important hunt, he dropped everything and drove back to your house, immediately. He...still loves you.
Dean desperately rang the doorbell, hoping to God that you were alive. A few seconds later, you opened the door with a smile that slowly faltered when you laid eyes on Dean. You were dressed up in a pretty dress and make up, obviously you were waiting to be picked up by a date. You asked Dean what he was doing here and he sighed, realizing Ben lied about you being sick to get him here and stop you from going on the date.
"We've been, uh...We've been 'parent-trapped'. Ben put out a S.O.S, and said you were sick."