Is there anyone you could go out with to give you some pointers and help boost your confidence? As most of the other posts say,Tonight, I did my first ride in the dark. Only 10.5 miles but I wanted to experience riding with lights on. To be honest, I did not feel comfortable, I kept checking the lights to make sure they were working and was glad to be back home. So now, I think I will stick to daylight, I feel much safer knowing my visibility is much clearer.
riding in the evening or late at night can be quite enjoyable once you get used to it and with a good set of lights your more visible to other road users than in daylight.