Upon entering the Roadhouse he had spotted you. He shouldn't be this surprised, he really shouldn't be. You had always been good friends with Jo. The Roadhouse was a place that you frequently stopped by.

Sam would have walked out of the bar right then and there if Dean hadn't given him a literal shove. The older Winchester knew all about the messy breakup between you and Sam. Quite frankly, Dean thought that the two of you had overreacted. He thought that breaking up over both being hunters was stupid. But, it was also a fool proof way to protect each other. Hunting was a dangerous life style. Neither you nor Sam had been ready for the difficulties of navigating a life together.

You looked as beautiful as you had the day that Sam had broken up with you. He felt a sudden punch of guilt. He should have tried harder to make things work. That's all that he was able to think about as he sat down at a table. Dean went to the bar to grab a couple of beers. Sam might have went with him if he hadn't been so nervous to see you again.

Sam hadn't been expecting Dean to sit down at the bar. He also hadn't expected to see you walking over, two beers in your hands. You set down one beer in front of Sam before sitting across from him. It was immediately obvious that Dean was meddling. The older Winchester refused to watch Sam pout about not being with you anymore. He had decided to do something about it, even if he had known that it would piss Sam off.

"T-thanks," Sam said quickly.

You had to admit, you didn't blame Sam for breaking up with you. Not one bit. Things wouldn't have worked out. Not then at least. You had both been too young to try working things out. Well, you weren't both teenagers anymore. Years had passed.

"Dean sent me over, I have a feeling that wasn't your idea." You took a sip of your beer, watching Sam's reaction. It was obvious to you that Dean had been trying to get you to talk to Sam.

Sam sighed, "We didn't exactly end on good terms. . ."