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@Fran
I remember when I first got a bike in London, I had to ride it home from Oxford St. I was so terrified of cycling along all the big main roads on my way home, but as soon as I got on the bike I had a surge of adrenaline and all my fear went away and was replaced by a super awareness that I didn't know I was capable of. I've never been afraid of cycling in London after that first time.
I think that even if you are riding with other people, at some point you will have to take a leap of faith. I think that the sooner you ride down a "scary" road, the better (that is once you are comfortable on your bike). You will feel a lot better once you do.