I have a funny story when I was in Milan. I was backpacking around Europe and went to Italy to visit a friend. We were in Milan and he took me to buy some shoes. He knew this crazy italian that owned the shop and he was extremely friendly and enthusiastic. He even set me up on date with his daughter that evening
I also went to Turin to watch Juve-Parma (goals from del piero and Nedved) and on my way there I got lost. I ended up on the wrong train with the wrong ticket, while two policemen were talking to me in italian about not being able to be on that train. Luckly an italian girl, that also spoke spanish, sitting next to me, understood the situation and explained it to the police. She gave me directions and even stayed with me to make sure I took the right train.
In Rome, was different story though. First, I almost got hit by a group of spanish speaking gay men. One guy was standing next to me trying to buy a train ticket but the machine was not working. He got so upset, hitting the machine and screaming things, in very gayly manner that I couldnt help laughing. He went running to his boyfriend complaining that I was laughing at him. Suddenly I was surrounded by a group of 6 very upset and very gay guys. I didnt get my ass kicked because a group of policemen appeared nearby and the guys left when they saw them.
Then one night I was walking back to the hostel and I noticed that an old man was following me. I went inside a pizza place to see if would go away but he also went inside and started flirting with me offering to buy me so pizza.

. I remember that I was just running like hell back to the hostel.
So all in all, I have fond memories of my time in Italy.