I used to hate riding my bike anywhere with cars and other vehicles around. I am just starting to get more comfortable with it, and I thought I'd share some of the strategies that have helped me out for those who are interested.
1. Go slow and steady
The whole experience of getting around on a bike can be pretty daunting for a beginner - getting in shape, keeping your bike upright, avoiding potholes, paying attention to traffic, not getting hit by a car, navigating, etc. I think the best way to deal with this is to start out slow - literally riding at a slow speed, so you're not breathing hard, and also taking fairly short jaunts to start with. As you get more confident, you can gradually build up to riding longer distances and/or a faster pace.
2. Ride with others
Especially on a longer ride or a ride to a new place, I feel much more confident and enjoy myself more when I ride with a friend. Riding with one or more people also increases your visibility to motorists.
3. Don't skimp on safety
Please buy and use a helmet. Ditto for a bell, and front and rear lights if you ever ride at night. Having the right safety equipment not only keeps you safer, but in my opinion makes you more confident on the bike. It is also wise to carry a multi-tool, a spare tube or patch kit, and a pump or a CO2 cartridge. You may also want to invest in something to carry cargo on your bike instead of your person, whether that's a rear rack with a milk crate attached, or some sort of fancy basket or panniers. Keeping your bike in good working order is also essential. You can take your bike to a shop for regular or tune-ups, or pick up a book on bike maintenance and do it yourself.
A pretty and functional bike basket seen on the streets of NYC
One resource I have been inspired by lately when it comes to bikes is Let's Go Ride a Bike, a blog written by two women who make riding year round look easy, fun, and even stylish. One of them lives in Chicago and rides her bike year round! The blog features how-to instructions and videos, photos of cute bikes and cute people riding bikes in stylish outfits, and plenty of inspirational ideas for ways to have more fun riding your bike, build connections with other cyclists, and more. I recently went on a bicycle picnic excursion with a few friends, after seeing it suggested on their blog. Photos from the picnic are below. I forgot to take any with the bikes, but I swear we rode them!