Certified Legendary Thread Awkward Flirting Stories

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The next morning we were due to attend a meeting with all of the big wigs of our agency at 9 a.m. Bill rocked up to the meeting around 10:30 a.m. with a sweat covered shirt. He had a massive stain in his black pants that I can only attribute to vomit.

He told us he had lost his mobile phone but he had no idea where. Our hotel was about a five minute walk (if that) near the bar we were drinking in and he paid a taxi driver $50 to take him there. He also came in to the meeting with a very severe limp, which turned out to be ligament damage in his ankle, which the other guy and I managed to convince him that it was when he slipped on a kerb while running away from the Police.

During the night Bill piled up our bourbon glasses then shortly afterwards knocked them all on to the floor accidentally. He picked up a chunk of glass from the floor and asked us if we thought it was glass or ice... We suggested he try it, which he did. It was glass :D. He also managed to scratch his name in to a chalkboard of the bar with a shard of glass, which I went back to a couple of years later and it was still there.
 

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Some small talk with a waitress after which i ask (when very drunk)

"What time do you get off?"
Her: About Midnight
Me: "Cool. When do you finish work them?"

Crickets. I am so lame. Thought it was a good line thou.
It is a good line, she was obviously just a humorless bitch :rainbow:
 
She then spent the next 20-30 minutes chatting with me about how much of a creep he was and asking how I put up with him, etc. I would've pulled without even trying that night if I wasn't committed to my long term relationship at the time :).
Whoa, best wingman ever! :p
 
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