Having been brought up in Asian RE, I have never finished any deals without having to meet some sketchy people just to get my stuff done quickly and properly. Suffice to say, I rarely get nervous when having to toe the legal line while working on a deal.
On one particular occasion, I had to meet some of my father's friend's friend to be introduced to some local guy who was a good friend of the local district head in order to get a permit through. Having been through a bunch of similar meeting, I was preparing mentally to meet some character in a coffee shop with the obligatory Rolex as a sign of goodwill, maybe some light hostess bar activities and that is it.
It turns out on a blazing Tuesday afternoon (over 38 Celcius), I had to meet them at a dog meat restaurant that is super close to my school. Sitting on a low plastic stool with with my fat ass, I was already uncomfortable as hell. To add to my discomfort, I was facing the prospect of having to eat DOGS just to get their approval. The man across from me further caused my stomach to churn. He was a bald, short man with a particularly severe case of Napoleon syndrome. Apparently he was my dad's acquaintance when he was thrown in Thai jail for 2 years. Started out with some standard chit chat; then it got weird the moment I gave him the Rolex. MF started looking closely at the 1675 Rolex GMT-Master; asked why I gave him a fake watch and threatened to fuck my chubby ass up. I tried to calmly explain that is it a very valuable vintage watch and he replied by calling me disrespectful liar. I was slightly scared at this point because he looked serious and from his reputation, he probably have some dudes ready to jump me if I seemed disrespectful.
Twenty minutes in and the entree came out, some pieces of meat with slightly brown skin steamed and served with local herbs and dipping sauce. Despite my substantial appetite apparent in my appearance, I never had dogs before. Supposedly giving a man a fake watch is one thing, not eating his food when invited is a severe sign of disrespect. At this point I had to excuse myself and went to text my uncle to come bail me out; he came 5 minutes later and iron things out with some jokes about me having a small penis. Having had my life threatened and my man hood insulted in a span of one hour; I was already prepare to call it a day. All of sudden, they moved the engagement to some weird spot outside the city. It was a strange motel/brothel; the bald dude said it is his treat and told me to choose one of the girls. It was all too much for me to handle so I called a cab and went back to the city. The deal never got done and I was so traumatized that would never I bring myself to meet any one of my dad's friend again.
What is the sketchiest experience of your life? It would be fun to read the stories.