What to buy, it depends on your budget. If you don't have any money, I will reccomend a Chinese Lifan LF250-4. I do own one and I am happy with it as a comuter. It's really cheap to buy and great gas mileage. Not the fastest on the highway, but still ok, I drove it with about 60 miles per hour, but it again depends on your weight. I am 200 pounds, so you can drive faster if you are smaller than I am. It's low and big and it looks great as a chopper. But if you are not so big, and you have a little more money, you can buy a Suzuki Marauder 250 or a Honda Rebel 250, or a suzuki GN250, or a kawasaki eliminator 250, that are way better quality. If you are big as me and more money buy a Yamaha Virago or a Suzuki Intruder, they are bigger, so your knees are not bent hard to find the pedals. If you want the street look, and have lots of money, go for a Kawasaki er6-n or a Honda CBF500 or a Yamaha fz6 fazer Abs. Still ok driving stance, but street looks. On these three expensive beasts, you get ABS, that can save your life sometimes. Harleys look great but are poor quality, they even sell Loctite on the website to glue the screws on. The sportbikes, ninja and the like are not confortable for comuting, you get tired in your shoulders, it hurts your bottom, and there is little space for a girlfriend. A chopper/tourer/cruise is very confortable and it has great confort for the girlfriend too. Don't get for a 100cc because it can be dangerous in the traffic. Sometimes I feel like I need more power to keep it up with the traffic, and mine is 250cc. If you have really low budget, go for a scooter(moped) I had a Taiwanese PGO HOT 50for some years now, very good gas mileage, very reliable too (already 25000 miles on mine). I still use it in the city and for shopping(lots of place for the groceries and stuff). I don't know if in your country it's allowed to have a pillion on the moped. In my country (Denmark)it's forbidden to have the girlfriend as a passenger (or any passenger). One of the things that are never told, it's the fact that most bikes are made for long legged people. If you are not so tall, or not so long legs, go for a chopper / tourer/ cruiser and the like, because they are low seated. When I'll be richer, I'll get a Yamaha Virago 700 or something. But until then, I'll ride the Lifan.