Well, it will make your trans date care about you. As flattering as it may sound, most trans women like to hear it described. For transgender women, they are constantly working on their looks and hoping for recognition. They want to look sexy and beautiful like a cis woman. Therefore, appreciation of her appearance is also an affirmation of her efforts. But sometimes you should pay attention to what you say. You may think you’re playing a slick playboy, but you end up as a failed playboy.