Timolol is a nonselective beta-adrenergic antagonist with no intrinsic sympathomimetic activity. Conditions like intraocular hypertension (IOH) and primary open angle glaucoma (POAG) warrant the use of a topical ocular preparation of timolol. It works to effectively lower the intraocular pressure (IOP) in patients with glaucoma but due to its unique pharmacodynamics, it also poses some very striking systemic side-effects. These include heart block, arrhythmias, and syncopal episodes. Herein, we present a challenging case of a previously known healthy elderly 67-year-old female, known case of POAG, who presented to the clinic with a very peculiar complaint, i.e. episodes of her head dropping down on to the table multiple times after she was done eating her food. This led to a cascade of diagnostic tests being employed encompassing cardiovascular, endocrinal, neurological, and gastrointestinal systems; all of which came out to be negative. Finally, after a very thorough literature review, it was established that timolol was the true culprit. The cessation of the drug immediately resulted in lasting relief.