Oh yeah, Milan was an awesome experience, and not just for "nice" reasons.
I got stranded at the metro/underground with my flight out cancelled, and my phone was dead so I couldn't contact my friend that I wanted to come back. I wasn't being able to find any phonebooths either. So I tried asking a passerby if I could use his phone. Except the guy, being a big-city busy-life guy continued walking. Figuring he might not have heard me (he was wearing earphones, and I'd have stopped someone else, but there weren't a lot of people around), I walked behind him. He saw me coming up behind him and started walking faster. I started walking faster to get to him. In the end he was almost running, with me, this big burly beardo going after him yelling "Telefono, por favor!" and even raising up a 2 euro coin :D.
...thankfully I found a phonebooth eventually.
As far as prostitutes go, while my friend was at work, I ventured out alone for lunch, trying to find this place I had noted on the internet to eat at, and there was some seriously heavy rain, and I wasn't being able to find it. Constantly doubling back and going forward, I guess I must've looked suspicious, because this woman approached me. With me not really being able to speak italian, and coupled with her fairly conservative clothing (plus it was really raining) I wasn't getting what she wanted. Finally, frustrated, she said in english "Oooh baby, baby, sexy", which got me bursting out laughing.
Since such a situation was very novel for me, I asked her in broken spanish if I could take her photograph, to which she agreed :D.
And yeah, the Duomo roof was awesome. When I went, the elevator was broken (or maybe I was too much of a cheapskate to pay for it, I can't remember), so I had the 'pleasure' of walking up. Worth it, of course.