Which secrets? XD He'll probably tell her that he's Gear, but not sure if he'll bring up that he's gay unless something prompts it in the conversation.
Richie kind of goes for the more muscular type and yours are a bit on the slender/thin side. But he would be more willing to compliment Duo on his hair.
Rapunzel will skip soundboarding. That'd one of her inhibitions, always needing a second opinion before just DOING something. She'll go straight Yuri and Flynn and tell them. But she and Duo can still do something fun together!