Over the years that Supernatural has been on, Dean Winchester has been with numerous women, Cassie Robinson, Jo, Leyla Rourke, Lisa Braeden, Andrea Barr, Carmen Porter(Fantasy girlfriend of his), Anna Milton and then women he met in bars. and then the mother of his child.
Of all these women I truly thought that Lisa would be the one for him, but that didn't pan out. and now they are bringing in a new girl by the name of Robin who met Dean some Twenty years prior. So that makes her his childhood sweetheart and we all know what that means.
A childhood sweetheart is that one person that we loved...
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