Italian is a simple language. Lived in Milan for almost 16 months. My Italian is still better than my Russian (Russian will make a Westerner cry). Just listen to Italian pop songs. That is how I learned. I also read a lot of s----- tabloid stuff. There was once a site (studenti.it??) where I picked up a lot of slang. Just dumb yourself down. Get into the simple basic stuff. That is how you pickup a language. Women's magazines are perfect. They are easy to read. Sports magazines can be quite good as well. Make sure there are a LOT of pictures. Those magazines are the easiest. Will be hard finding much in America. There are really no Italians (born and raised there) living in America anymore.
Don't forget about dialects. You still hear them. Also accents vary. As an American I found Bologna to be a place with a clearer accent. Milan has some really rapid fire Italian. The South speaks with a drawl and more singy songy.
http://www.youtube.com/watch?v=0w40c3g3WTs
http://www.youtube.com/watch?v=GF0F1fEJa_4
Lunapop was HUGE when I was in Milan. From Bologna. The songs are simple and it gave me a lot of confidence with the language.
Here is what a lot of guys I knew listened to! If you like discos with a lot of teenage girls and guys twice their age who still spike the 5 hairs they have this is for you! Also big in Austria and parts of Eastern Europe.
http://www.youtube.com/watch?v=AbekPLjHZak
As far as girls...Don't think about it. Italian females are not usually that attractive and are hard to get to know. EVERY Italian guy is planning a trip to Riga, Tallinn, Prague, or even Kyiv these days. I will say that I love the family atmosphere. Mothers are SENSATIONAL! It is normal for 40 year old men to still live at home and live as teenagers. The sporting events are off the hook. Lots of free concerts from big name entertainers (in front of the Duomo in Milan there were always massive concerts for free...Black Eyed Peas, Duran Duran, etc.). Bars and clubs are very interesting. Usually just a bunch of guys walking around in them. Saw Gabry Ponte a number of times! People also walk A LOT. Guys just walk around at night and daytime. Partially because most 30 year old guys are still living at home as 15 year olds. Makes it easy to be alone at night. You just walk around looking at things. Lots of guys do stuff all alone as well. People also spend a fortune on clothing. They also tend to drink espresso standing up. You pay and then go to the bar. Same with eating pizza. I spent a lot of time in Autogrills and Breks. Breks offered very nice traditional food in a nice easy to get setting. Loved how you could get the wine or beer yourself from the tap! Was cheaper than Coke. Basically, most of my free time was spent drinking coffee, soccer, basketball, discos, and Brek. Favorite places in Milan were Emporio Armani Cafe, Il Cova, the Brera district, San Siro, Fila Forum (basketball games...Armani Jeans Milano), and Stazione Centrale (the train station where I travelled to mainly Como and Lugano). Lugano, Switzerland is stunning! Gorgeous views and much nicer than anything in Italy. I love the Swiss. Can't forget about Via Montenapoleone either!
http://www.youtube.com/watch?v=-VyVcBga2Gw
This was THE SONG when I was there. Nothing bigger. Massive Italian pop/rock hit.
Another great song...
http://www.youtube.com/watch?v=s9Dmb6ttsXE
You can learn Italian at home. Just buy a bunch of books and work on it. It is a neat and simple language. Remember, don't make it sound like Mexican Spanish! It has its own flavor. Sounds a lot like Argentine Spanish. Use the Internet. Tons of stuff out there. Start following Italian soccer (calcio) or basketball.
Here is a funny story. When I was there I noticed some youngish girls who were just gorgeous. They would be on the metro carrying these binders. I had no idea what or who they were. They were young and about 5'9". Did some research and realized they were models. Milan brings in a TON of East European girls to build up their "books". And no, you aren't going to get to know any of them. They are what led me East! So, Italy will always have a soft spot in my heart because of them.
