Nightwing Basically Dated Red Hood (& It Ended Terribly)
Despite both being trained as Robin by Batman, Red Hood and Nightwing tend to have a contentious relationship. Dick Grayson is the embodiment of hope, while Jason Todd is a cynic whose rage at the world can often lead him to extremes. Of course, the two care about each other, and so the tension in their relationship only serves to make their moments of connection all the more meaningful. However, one of Nightwing's romantic relationships effectively saw him dating the female equivalent of Red Hood, and it ended in disaster.
This relationship was with Shawn Tsang, a former sidekick who had an acrimonious split from her former mentor. After a period of darkness and self-reckoning, Shawn committed herself to atoning for her prior deeds, attempting to make the world better in sometimes illegal ways, never considering herself a 'hero.' If this sounds familiar, it's because it also charts Red Hood's own journey from Boy Wonder to gun-toting antihero. The big difference is that rather than being a teen hero, Shawn was the villain Defacer - a young 'art terrorist' who worked with Batman villain the Pigeon to carry out illegal protests and vandalize landmarks.SCREENRANT VIDEO OF THE DAY
Related: Joker's Nickname for Red Hood Confirms the Real Way He Broke Jason Todd
With a disdain for traditional authority and the expertise to do something about it, Defacer's attitude is very similar to Jason Todd's, including her desire to help those who remind her of her younger self. It was this quality that created a point of connection with Nightwing, and the two grew closer when Nightwing was targeted by Doctor Hurt and Shawn was accused of murder. They ultimately broke up due to their differing attitudes to crime and punishment, with Shawn holding to many of the criticisms of Gotham vigilantes that Red Hood has lobbed at the Bat-Family. Another way in which Shawn and Jason are similar is their explosive tempers. When Nightwing was shot in the head and lost his memory, Defacer took offense at him 'ignoring' her for months and vandalized a statue of the hero, with her arrest giving Amanda Waller an excuse to force her onto the Suicide Squad in Suicide Squad: King Shark (a fate shared by Red Hood in the recent Suicide Squad: Get Joker.)
That's not to say that Shawn and Jason Todd are the same person - Defacer may lash out at a complacent society, but she never shot anyone in the head - but they do have remarkably similar dispositions and histories. This makes her bond with Nightwing particularly interesting, as it shows how Dick interacts with Jason's personality type when their history of animosity isn't in play. It's therefore telling that Dick felt such a connection to Shawn and that their relationship ended so dramatically. Jason and Shawn's fiery passion, distrust of authority, and sense of responsibility for those who society discards are qualities Dick actually admires, but they're also traits that ratchet up the hard feelings when things go badly.
One of the most fascinating questions about Dick and Jason's relationship is how they'd interact if they were able to meet each other fresh, and the former's relationship and later friendship with Defacer suggest they'd bond over more than the Robin legacy. Sadly, it also indicates that Nightwing and Red Hood's disagreements may be destined to always get out of hand, even as Dick is capable of seeing more to admire in Jason than either of them might suppose.