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A big part of Pippa's charm is that mask she wears when interacting with people slowly dropping as she becomes comfortable. Earning Pipper's trust and getting to see the real her, for better or worse, would make all the effort that much more meaningful. Seeing her real smile, hearing her real laugh, knowing that they are real and not some persona, and that you brought them out is amazing. It would be a lot of effort, and require constant self-awareness, but I can't think of a better reward in the world than becoming the person that Pippa is simultaneously the most aware of and the most relaxed around.
I want to woo the Pipkin's room mate. I want her to only look at me. I want to be the greediest person in the world and have as much of the real Pippa as I can.
I am being 100% honest with myself here. I think that Pippa is far more beautiful than her self-degredation makes her think. As strong as her sense of self may be, I believe her truest self lies behind a fragile and infinitely complex puzzle that require patience and dedication. If you try to cheat your way to her heart her with dishonesty or force you will get nowhere. In the worst case scenario break her. I want to talk to her, let her grow to know who I am, prove to her I am the man I think I am. I want to peel away those layers and layers of defense mechanisms and coping skills until she blossoms. The is staggeringly beautiful in her complexity, and people that say she is dumb or gullible are just blind to the truth.
Pippa, real beauty isn't on the outside. I know you have trust issues and think that your inside is just as scarred as you think the outside is, but I am telling you that isn't the truth. You have something very special and precious inside you, all I am asking for is the chance to come a little bit closer. After that it is up to you to decide if I am worthy of your trust. No matter what you decide I promise you that I will abide your decision. If you tell me to go, I will go, if you decide to allow me closer still I won't overstep your bounds. I am willing to take as much time as you need. You are worth it and one day I wish to prove it to you.