Yes!. Our daughter and her husband are LEO. They tell us that this sort of thing happens all the time. Sometimes the thieves work as teams, sometime solo. The perp looks for a single male at the bar who appears distracted -- watching a ball game, looking at his cell phone, chatting with the person next to him, etc. The perp slips something into his drink. As the drug and alcohol take over, he gets confused, unsteady, and on the verge of blacking out. The perp plays good Samaritan and assists the guy back to his room. He passes out and she robs him. The next day, he has no recollection whatsoever and if he is married, he may be too embarrassed to file a police report because he has no recollection what happened and his wife may think he cheated with a whore when his only fault was not watching his drink at the bar.
My wife thinks she witnessed this at a hotel bar in Miami a few years ago. She was sitting at a table that faced a mirror that reflected the bar. She saw the perp quickly drop something into a guys drink and then the perp went to the restroom. My wife told the guy what she saw and when the perp came back an saw my wife talking to the guy, she took off.
It does happen.
During my misspent youth I witnessed something similar at a bar in Europe. It was two middle aged British guys and a younger college age local girl. I didn’t see the drink drugged but the whole situation was wrong. Two guys, one girl. Trying to “help” a woman out of a bar. She could barely walk and had lost a shoe. The guys were playing “good samaritan” but I didn’t buy it and alerted security. There is a difference between plastered drunk and drugged. She was drugged.