After seeing a post about this site becoming like Facebook, I figured that I might as well sneak this thread in.

So, as the title suggests, what have been your most awkward encounters since you started punting?

This is probably a repeat of other threads, but I did a search before posting this and came up with nothing.

I'll start.

First punt - in fourways at a venue. Can't recall the name. It was before I knew of ESA's existence. I went to the venue solo because I was still embarrassed at what friends would think if I asked them to tag along. I ordered a drink so that I could scout what the general atmosphere was like. Finally, a lady caught my attention, but she was busy with someone who I assumed was a punter. After she went to the ladies, I approached the guy...hoping to get a bit of advice on how things are done. After chatting to him, he asked whether anyone had caught my eye. After telling him, he uttered the words "that's actually my girlfriend, but feel free to book her". I have never been so embarrassed in my life. I booked someone else. It was my worst punt ever. Paid R500 for what felt like 5 minutes.

This one took place in Cape Town, I booked a lady who is probably in my top ten "most attractive" in this industry. She was half Portuguese, very pretty with a nice hourglass figure. I made arrangements prior to my trip to Cape Town. We exchanged messages via email because she wanted to get a feel for what I like.

Arrived at her place that evening only to find her with her boyfriend/husband. That threw me off a bit as he was much older than me. He said he usually does a meet & greet with punters before the booking. It was so awkward, haha! He went on his way and gave me pat on the shoulder and said "have fun".

Similar experience. Had a regular I saw at a venue for a couple of years. They used to order me a cab to get home. Cab driver was always same fella. Finally figured out he was the regular's boyfriend which was a little awkward at the time.
This went on for a good 18 months or so. Eventually she left the game and I had to make do with other options (and taxi okes).
About 9 months later I ended up getting a lift from him from another spot and he said they had split up and that this girl had been looking for me. He called her up there and then, I exchanged details with her and now I have a lekker fuck buddy/booty call if the need arises who only costs me a couple of drinks.

Just a few days ago...I open the door, just to see the familiar face of a guy I used to date about 15/16 years ago. He knew full well who I was (I show my face after all) and planned it this way. It ended up being quite exciting to know he planned the surprise lol.