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Sam has feelings for you. It wasn't a secret to anyone but you. Dean could tell, Bobby could tell, hell even Cas could tell. It wasn't until Dean told him to ask you out today that he would have actually tried to. Hunting was the only reason he hadn't yet. This life style wasn't made for relationships. But Dean knew how important you were to him and basically demanded him to say something to you.
Just as he parked the impala in parking lot of the restaurant you worked at, he saw you walk out...with someone else. You stopped for a second and gave them a small kiss on the lips before lacing your hands together and continued your walk home.
