A few months ago I experienced one of the cockiest pick-up attempts that completely worked.
I was standing at an elevator bank in the building I work at. In front of me were a bunch of people, one of which was a very tall guy. Built like Captain America, blond hair, blue eyes, and a chiseled jaw line that just begged to be traced. He was the last one into the packed elevator and I decided to wait for the next one to avoid the claustrophobia. He saw me back away and joked that I was small enough to fit, and held the elevator for me.
I got in and hit the button for the top floor. Captain America with his superb powers of observation took notice and asked if I would be the one meeting with him. I looked up surprised and said no. He laughed and started trying to guess where I work (still on a very crowded elevator where everyone was trying to pretend not to listen.) As he got off on the floor below mine, I finally told him I worked on the third floor - and the doors closed.
I went to the top floor to sign in, and I had to pass this group of men standing around the foyer. I didn't think much of it, we usually had people coming and going all the time. I signed in, my name, time, and my place of work. Then went back to the office where I work.
A few hours later the door to the office opens and there is Captain America grinning at me and laughing at my phone conversation. It turned out the guys in the foyer were his friends and had told him where I signed in, he used that information to track me down.
We went out for about two months. He was much older but very attractive. In the end we had communication issues, he would say we should make plans and not follow through. Or text me, and take ages to reply to my replies. I finally just gave up and moved on.