Just some questions

1) When ever i go to sleep, my du-rag keeps on falling off. My barber said i have to train my hair before i get waves, so its a really low-cut right now. When my hair grows out, will the hair keep the du-rag my head?

2) My routine the night before 1. After i rinse out my hair, i put in some moisturizer, brush that in 2. i put in some lets jam (orange top) brush that in 3. Then i put in some sportin waves, brush that in. Then in the morning, i put on some lets jam (orange top) brush that in, then i spray some oil sheen for some shine