I was taking a beginning swimming class at my school to learn how to swim and I thought that diving headfirst was scary at first, but then it wasn't after I did not think about it anymore. My 2 options were "be able to do it and pass with an A" or "not do it and pass with a B". I did not think about it and all I did was just got into the diving position and let myself fall in head first.
I know its better said than done, but just let yourself fall in. Start at the edge of the pool with one leg in front of the other leg and hands above your head in a curve position ready to fall in. When it comes to new things, I get really nervous and scared for my first time. Jumping in the pool for the first time was hard for me to do too. Everyone kept telling me to jump in and I keep saying "I will, I will". What makes me nervous was people looking at me. What I did was sit at the side of the pool and just push myself in and that is what got me to stand up and jump in and to lose the fear
Note - when I first started diving, I was belly flopping and that does not really feel good. Make sure you go head first (very important).
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