SkunkyArt | MaximumDisrespect — It's Bad Luck, Isn't It?

Both are veteran warriors who've spent a recent period of their lives hunting down monsters (Corrupted Gems and Grimm)

Both have struggled with a low sense of self-worth (Pearl’s past as part of a servant race gave her low self-esteem, leading her to believe she must constantly prove herself as valuable to her teammates. Qrow sees himself as a dangerous burden due to his Misfortune semblance, which leads him to believe he’s better off away from anyone else, including his loved ones), both of which they have unhealthily coped with (Pearl’s need for constant approval from those around her, Qrow’s alcoholism)

Both are/were one of the most trusted allies of an authority figure who is/was widely viewed as wise and benevolent (Rose Quartz and Ozpin)

Service to this figure helped to alleviate their self-esteem issues (Rose treated Pearl as a friend and equal, showing her she could be more than just a servant. Working for Ozpin made Qrow feel like he was actually doing good work rather than endangering everyone around him.)
- Their reliance on this allegiance to fuel their confidence causes their mental states to plummet whenever their relationship or trust in this person is damaged (Rose's death left Pearl feeling lost, and learning that Rose even kept secrets from her caused her to have a mental breakdown in Rose's Scabbard. Learning that Ozpin had no idea how to defeat Salem and that they were essentially fighting an unwinnable war caused Qrow to lose faith in Ozpin and himself)
Both Pearl and Qrow were trusted by their leaders with dark secrets about their pasts and the true nature of the wars they were fighting (Pearl was the only person who knew Rose was Pink Diamond and that The Crystal Gems were led by one of the Diamonds they were fighting against. Qrow was trusted with the fact that Ozpin is thousands of years old and that the Grimm have a malicious leader who is actively plotting the fall of Remnant)
- Some of these secrets were revealed to the rest of their teams in an episode that consisted of the main character(s) walking through distant memories (A Single Pale Rose and The Lost Fable), which caused discord amongst them

Both have taken steps to break out of their bad habits to grow as people (Pearl learned to find value in herself rather than in others' approval. Qrow gave up alcohol)

Both lost a friend and leader named Rose (Rose Quartz and Summer Rose) before the events of their shows. During their shows, both of them act as parental and mentor figures to their leader’s offspring, who both happen to be the main characters of their series (Steven and Ruby)