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Diphenhydramine is a widely available, over-the-counter medication used for allergies and as a sleeping aid. When used in prescription doses, it is generally safe. Overdose of the medication has been associated with dangerous and life-threatening outcomes. Our case describes diphenhydramine toxicity manifesting with two rare but potentially life-threatening complications, rhabdomyolysis, and QT prolongation. Laboratory testing for diphenhydramine levels are not widely available. We recommend a high degree of suspicion for these complications when evaluating patients with diphenhydramine overdose, to adequately manage and prevent untoward outcomes.