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Before tightening, hold the tie with your middle finger and thumb and use your index finger to press down the middle. With this grip, tighten the tie. It works every time for me. Holding the dimple in place before tightening it is the way for me.
usually yes. Unless I'm in a hurry, I'll retie to get the dimple.
I aim to never have a dimple.
I have found a successful dimple depends upon the knot as well as the tie. I was rarely able to do it with four-in-hand, but hit it every time with a Pratt knot.