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So I am a complete newbie in the cycling world but I want to learn to cycle and use it to explore the city and the places yonder. I also intend to use it to ride daily to office gradually.

So my question is that should I buy a cheap/used bike to learn to cycle first, or buy the bike I like Trek DS or similar and learn to ride on it? I ask this question as I might be overlooking the wear-tear or other points before I make a hasty purchase. I am in my mid-twenties (yes, you can shame me for not knowing to cycle) and I like in a bike friendly city on the east coast. Thanks

I learnt to ride in my 20s. I couldn't find a big enough bike second hand, except by spending several times the price of a cheap new bike. So I bought a cheap new bike and learnt to ride on it (a steel so-called mountain bike but really a hybrid with knbbly tyres). Even that was actually only just big enough. I didn't really get confident in bike handling until I bought a much nicer hybrid that fitted me properly.

If you can possibly get a decent hybrid or hardtail mountain bike second hand that fits you that's the way to go. This will help you find what features you want, as well as being something to learn on; you may even find that this is a good commuter long-termn and you get something nicer/more specialised for having fun.

There's no shame in learning to ride as an adult, in fact quite the opposite - good for you.

I'd suggest getting a used bike because you can resell it for less of a loss if you find it doesn't meet your needs. You still may want to buy it from a reputable dealer rather than an individual to ensure it's mechanically sound. Ask about a warranty, and get it in writing.

Having acquired the bike, please be sure to not only learn the basics like balancing, braking, shifting, etc., but also how to ride in traffic. I'm pretty sure that most of the cycling organizations in major U.S. cities offer some kind of confidence-building classes. In Washington, DC, the best resource is the Washington Area Bicyclists Association. If you cannot find one of these classes that fits your schedule, pick up and read a copy of Effective Cycling by John Forester. I read it when I had 20 years of city cycling under my belt and still learned from it. Classes or no classes, bicycling clubs are a good way to meet people who are passionate about biking and can answer all kinds of questions.

I hope you find bicycling to be an enjoyable experience.

Buy the bike you like and learn to ride on it.
The Trek DS or something like it is a good bike to start on.

Any bike in the pricing/style zone of the DS will last years.

Welcome to cycling, it's a great sport with an amazing machine.

If you don't know how to ride a bike yet, then you don't know what kind of bike you'll enjoy riding yet. So I wouldn't commit too much money up-front. In fact, if you have a friend who has a spare bike they'd let you learn on, I'd just borrow one for now and learn on that so you can start figuring out what you like/dislike/need. Failing that, I'd get an old beater on Craigslist.

Once you've got all that figured out and are ready to get a "real" bike, test ride a bunch of bikes and take note of what you like and dislike about each of them. If you've got a good bike shop, the folks at the shop will be able to help you refine your choices based on that feedback.

I'll also mention that becoming a competent cyclist is an ongoing process, and there's always room to improve one's skills. As you develop those skills, your wants may change further.

Welcome the dilemma of getting a starter bike when you are not sure what kind of bike you want and don't know if you will actually like cycling or will keep it up. The problem of course is that you don't want to spend too much money on something you might end up not using.

The advantage of buying new is that you can go to all the local bike stores, get advice and test ride lots of different bikes. You can take your time choosing what you want and you'll be much more likely to get the bike that suits you in the size that fits you.

Buying used means paying less, but you have to know what you are looking for. If you don't know how to evaluate your fit on the bike you could end up with a bike that does not fit you well. You also need some idea of how to evaluate a bikes condition. A worn drivetrain can make the bike inefficient, badly adjusted derailleurs can make shifting gears a pain, and poorly adjusted brakes can be downright dangerous.

The other problem with used bikes is there are far fewer bikes to choose from at any given time. You have monitor spaces where used bikes are offered for sale (Craigslist and Facebook marketplaces seem to be the best options) and act on anything that does come up that matches what you want.