What was your "wait... What!?" moment?

While I was in high school my grandparents employed a 6pm-6am caretaker for a couple of years. I'll refer to her as Sally. Sally was loving, vibrant, and the understudy of a preacher at a fire and brimstone Baptist Church. The entire family adored her and even asked her to perform the eulogy at my grandma's funeral. My brother, on the other hand, found her to be "off" and occasionally inferred that she smoked crack. On these occasions, our dad would call her "quirky", proceeded to lecture him, and then threaten us to never speak of such things in front of the rest our family OR ELSE. All the while our mom would listen in utter disappointment, sorrowfully reflecting on how she could have possibly raised such a racist young man. I, as well, found him to be quite judgmental towards Sally. A year or so later on one fateful day, I'm impatiently waiting in line to buy gas. I find myself looking around and glance over at The Jailhouse Times (local newspaper showcasing the previous two weeks of arrest/mugshots). There she was on the front page. Double take. ...Is that Sally?! No FuCCkKinG way!!!! I begin to freak the fuck out within the confines of my own mind, to the point where the cashier laughs and inquires who it is that I know. I go ahead and buy 6 copies and totally forget about needing gas until I walk outside and see my jeep. She was arrested for trespassing, assault, and intent to sell cocaine. I called my brother, allowed him his well deserved "I told you so" rant, then told him I needed to call mom. He begged me not to, instead he wanted to set up a few nanny cams we already owned and watch her for a week. I agreed. Turns out she had an impressive amount of customers and was dealing on my grandpa's driveway.

/r/AskReddit Thread