Surviving the Supernatural world is no easy feat, and there's one rule that could greatly improve your chances: never date Sam Winchester. While the Winchester brothers may be dashing and charming, their monster-hunting lifestyle is not conducive to a successful love life. Throughout the fifteen seasons of Supernatural, both Sam and Dean struggled to find lasting love, with only one exception. Sam's wife, who is implied to be Eileen Leahy but never explicitly confirmed, comes into the picture after Dean's untimely demise.

In general, dating a Winchester is a bad idea.

Unless being pursued by demons and purchasing excessive amounts of salt is someone's idea of romance, it's unlikely they will find a stable relationship. However, it's Sam Winchester's track record with girlfriends that truly raises concern. Among all of Sam's love interests throughout the series, an alarmingly high number had ghostly endings. Sam Winchester's tumultuous love life began in the very first episode of Supernatural with the tragic death of Jessica.

She was murdered by the same yellow-eyed demon that had killed Mary Winchester. In season 2, Sam developed feelings for Madison, a werewolf.

Despite the brothers' efforts to find a cure, Madison realized the only solution was for Sam to end her life. This deadly pattern continues as Sam enters a demonic romance with Ruby in season 4. However, their relationship ends in tears after it is revealed that Ruby's loyalty lies with Lucifer.

Dean then kills her by stabbing her in the stomach. The pattern repeats itself with Amy Pond, a kitsune from Sam's past. Once again, Dean intervenes and kills Sam's monster girlfriend in season 7, along with the hunter-with-benefits, Annie Hawkins. Sarah Blake temporarily believes she has escaped the curse of dating Sam Winchester after surviving her initial appearance, but Crowley later orchestrates her demise seven seasons later.

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