He kind of liked lowering someone's guard after a stressful moment. While he wouldn't be able to watch the contract being made out of respect and privacy for everything the Ringmaster did, he would enjoy teasing Rip later that she essentially did it to herself.

He glances down for a moment towards her soul and he can already tell she wasn't human but this was a prime opportunity for information, "Now you have to tell me. You've piqued my curiosity, Miss Winkle." It would be nice to put a soul to a reference.