Should I buy an urban cruiser bike, and is a single-speed version going to make me happy?

I would strongly recommend that you: 1) Test ride bikes in a typical city environment. I know that you said that your commute is pretty flat, but IIRC, there is a bigass mountain right in the middle of the island. If you ever has reason to drop by McGill or to cross the center of the city, you want to know that you and your bike can handle it. 2) Balance the cool looks and many recommendations you will get for "comfort" bikes with the way YOU actually feel when you ride one compared to a hybrid that will have you ride in a slightly lower position. I know that I have a habit of getting cranky-to-evangelical about the potential perils of cruisers in AskMe. I know that other people feel completely comfortable in these upright frames, and some people feel less comfortable in less upright bikes (they want to be able to see around them more easily, or putting a little more weight on their hands versus their butt actually makes them sore). But my experience on different bikes at different levels of fitness have left me feeling that an upright bike with relatively few gears is AWFUL if you have to go up an incline or carry a load in panniers on your back rack. These bikes are usually heavier than a comparable hybrid, and the upright position means that it's hard to engage your torso to work with your legs when you pedal. The bike shop should be able to offer a variety of bikes for you to try. If they try to sell you on just one or two, feel free to go to another store and see what they have. Cruiser or comfort bike: potential problems with overall weight and that upright position (your bio-mechanics may vary). Single speed: easy maintenance, but choosing the right gear ratio for your environment is tricky even for a fit person with great knees. Gears: I can see how 3, 5 or 7 gears may seem more sensible than 21 or 28 gears. You may have already seen that there are a lot of gear settings that seem redundant or which seem too hard or easy. But that number of gears offers your the finest gradations in ease of pedalling. If a 21 or 28 bike feels good, don't throw it over for fewer gears unless that other bike feels as good to ride. You will probably be bringing a bike to a shop for spring tune-ups instead of doing it yourself, so they will be able to deal with any number of gears just fine. Last thing: I like that while you're aware of your current level of fitness, you're also ready to challenge yourself a little. Don't hamstring yourself with a bike that is too limited and too heavy to make riding pleasant NOW. And please, please, please: try to stay out of the hardest gears. I know that it can feel good to mash the pedals, but your knees will thank you if you take it easier on them.

And http://www.solocycle.ca/pictures/bike038-1.jpg!

Also, try to avoid suspension (front or rear) if you can. They unnecessarily add weight and again perceived weight, converting your energy into useless up and down motion when you need it most converted into forward motion.

Oops, my friend hadn't been going there for ten years, as the shop hasn't been around that long. :D

I had a bike like the sort you describe a couple years ago that I got for the purpose of commuting. I really hated it. It was heavy and awkward. Last year I tried a hybrid Miele and fell in love. It was around $500. It is so much easier - easier to pedal, easier to maneuver, etc. All of which is to say I would recommend 5 gears (three at minimum). Also, as OHSnap said, definitely try every style of bike you can afford so that you don't turn out like me and decide you hate the bike you bought and have to start the search all over again. And yes, as soon as you step up a level from Canadian Tire and go to a good bike shop the brand issue isn't too crucial. Just get something you love from the outset!

After all of this excellent advice, I went to a different shop, http://www.solocycle.ca/en/index.html - a small one-man band in my neck of the woods that was recommended by a friend whose family has been using it for ten years. I explained my needs, he picked out a couple of suitable second-hand hybrids that had been completely fitted out by his own hands. I rode one around the block and fell in love instantly. Not only was the price good, but it came with a list of the issues it had when it was first brought in, all of the repairs and new parts by brand name, and a personalized bike biography ("... its former owner said she called it "The Jolly Jumper," after the trusty steed of Lucky Luke."). He gave me a crash course in bike maintenance and spent 5-10 minutes checking and tweaking it before letting me ride away, and it comes with checkups and a guarantee. Many thanks, Metafilter! If it wasn't for you all, I'd have gone and paid more for a new and probably unsuitable bike, instead of the fabulous (and soon to be renamed) Jolly Jumper. Awesome.

Excellent comments so far. Keep in mind that bikes, in general, are a compromise between comfort and speed. Beach cruisers are the most comfortable, and frustrating difficult to pedal anywhere. Road race bikes are uncomfortable to sit on because you should be putting all of your weight on the pedals if you're racing. Decide where you'd like to be on the comfort-speed spectrum. The two biggest determiners of bike speed/comfort are rolling resistance and aerodynamics (at low and high speeds, respectively). Rolling resistance is proportional to tire pressure. Because of manufacturing constraints, maximum tire pressure is proportional to tire width. If you decide you'd like your new bike to be faster and less comfortable, get skinnier tires and keep them at maximum inflation. Most bikes have clearance for slightly wider tires. Aerodynamics are most influenced by posture, or the difference in height between the handlebars and seat. Road racers may have handlebars a foot lower than the seat, but you're probably better starting close to level. If that's uncomfortable, raise the handlebars. Ask your bike shop about this or get an adjustable stem to start. You're not changing the seat height because there is only one correct seat height for your hip-to-foot length. Sitting up straight is comfortable at first but compresses your spine with each bump. Folding forward to absorb the impact with your arms is much better for you. The really wide comfy seats are designed for an upright posture and the narrow road racer seats are designed for the forward-rotated hips of a horizontal back. Choose an appropriate seat along this spectrum to correspond to your posture if you significantly change your bike's handlebar height. Also keep in mind that most experienced bicyclists unweight their saddles and loosen their arms when they're about to hit a bump. This takes practice but makes biking much less fatiguing. Take a one-day cycling techniques/safety class and you won't regret it. Don't worry about weight too much, especially if you're carrying a bag and a three pound lock.

Seeing as how you are in Montreal, you do have a rather large hill to contend with if you want to get around for reasons other than your commute. If, as you say, you are not in the best shape, a single-speed bike may not be ideal for this terrain. A heavy single-speed would be even less ideal. Dutch style bikes, such as the http://www.electrabike.com/Bikes/amsterdam-bikes-electra you mention, or http://usa.batavus.com/. Often have internal gearing in the hub of the rear wheel. Traditionally this has been three-speed, but more recently you can get 6- or 8- speed hubs on some models. Both http://www.linusbike.com/ and http://publicbikes.com/ now make this type of bike in North America. Many people select these bikes on the basis of practicality and aesthetics, but the issue with them is that they are still quite heavy. This has to do with the design, and the type of steel used in the frame. Remember, the original designs come from a country with almost no hills. You may also be tempted by a http://en.wikipedia.org/wiki/Cruiser_bicycle. This will very likely not suit your needs- the laid back design produces very inefficient power transfer, and while they look fancy and are extremely stable, they are extremely heavy and exhausting to pedal for any distance. These may sometimes be called comfort bikes, but they are not that practical. Another option is the modern commuter or urban hybrid. Along with the Devinci mentioned above, and some of your Norcos (Norco, by the way, has kind of a mixed reputation- they have a solid history but turned out a bunch of garbage in the 80s and 90s. Apparently, they have improved again), you might also look at a http://www.trekbikes.com/ca/en/bikes/town/urban_utility/soho/ or an http://www.opusbike.com/en/bikes_7_9-87-belladonna.html. These will have lighter aluminum frames, lighter wheels, and external shifters with more gear options. Several may have disk brakes, which are great for wet or otherwise difficult conditions. They're a bit pricier, but you're paying for (lack of) weight, better-quality and more durable components, and greater reliability. Again, though, your best bet is to check out your local independent bike shops, and try a number of different bikes until you find the one you like. Make sure they adjust the one you pick to suit your height and riding style, and don't be afraid to go back to the shop if it needs further adjustment once you've purchased it.

Ugh. I have a 3-speed Electra, and while it's a nice bike, it's heavy and slow. I've abandoned it for a lightweight bike that is much faster.