Robin's not ashamed of his past as a thief. And when he needed to get Regina to open up, he stole the letter right under her nose so she couldn't deny something was bothering her.
As Robin attempted to woo a reluctant Regina, he was happy to meet her friend Tinker Bell. Little did he know at the time that Tink had already clued Regina in on Robin being her soulmate.
Back in the Enchanted Forest, Regina had little interest in Robin's help or opinions. That didn't stop him from offering his expertise when the heroes needed him.
Given the circumstances, we can't blame Robin for being suspicious of Zelena's intentions. He was more than willing to give his baby girl everything she needed.
After his wife's death, Robin raised Roland on his own. Given how happy the little guy seems whenever he graces the screen, we think he did a great job.
After swooping in to save Regina and Snow from a flying monkey, Robin attempted to do the chivalrous thing. He remained unfazed when Regina rejected the gesture.