Rorden's great disappointment is a current one: this tiefling prince *asshole* seems to be attracted to him. That he doesn't mind, but the guy insists on bringing *feelings* into it. Rorden considers sex and attraction completely separate from love and commitment and feelings. He's not ace or aro, he's interested in both, but his life experiences have never ever linked the two. So he's constantly exasperated with this man mooning over him. Not just because that's tedious, but because the man is offering something Rorden *could* want, but Rorden thinks the man lacks the emotional maturity to understand it, and also Rorden has a commoner's knee jerk dislike and distrust of the nobility. Rorden's considered himself unlovable for years, finally someone shows up and claims to adore him....and it's this asshole.

Sian's greatest disappointment was also fairly recent (but short lived, since after the messy emotional reunion they're trying to reconcile), seeing the person who had hurt him the most walking back in his family's front door. On the day of his brother's wedding, a day where he was already viscerally reminded that his little brother had found love and bliss and he was all alone.

Mary's greatest disappointment was asking her Grandparents about her real parents and finding out that her father hadn't wanted her.