I try on five more dresses, but I'm not happy with how I look in them. Something always seems off, and it triggers insecurities I didn't even know I had. Kent seems to think they all look great, but I don't feel a connection with any of them.

I pick a new navy dress from the pile. It has a flowing skirt and a subtle pattern. The straps are just right, and the neckline sits comfortably below my collarbones. The back is slightly low, but not too revealing; it doesn't go too far down my ...