My question is: why do I need to appear fascinating? I feel like I'm trying to sell something to people who can't see it in me. I feel like the right people already find me fascinating without me having to actively go about appearing fascinating.

Fascination is apart of attraction - people are drawn to you or they aren't. I wouldn't want a relationship based on all those times I tried to change their point of view of me. I agree with pushing yourself into uncomfortable positions, but not at the appeal of others.