Yes. Do it. Don't wait until you are completely comfortable. If the "scab" (gross analogy for seeking relationships, but hey i just won't date you then) has healed enough so that it has granulated over and won't bleed, then pick i mean rip it off.
Ripping off scabs... Hoo whee.
Heheheh 'pulling the scab off' was the only metaphor I could think of for doing something you anticipate is going to be painful but wanting to get past it/over it.