The romantic history of Dick Grayson has been a hot topic for decades, but his worst fling was with his mentor’s longtime love, Catwoman.
The many romances of Dick Grayson are often burning topics in the DC Universe. His on-again-off-again, will-they-won’t-they relationships with both Bat-Family member Barbara Gordon and fellow Teen Titan Starfire have piqued readers’ interests for decades. Whilst that love triangle has reached a resolution (for now) in the pages of Nightwing, that doesn’t mean Dick hasn’t made his fair share of mistakes when it comes to love.
The original Boy Wonder hasn’t always gone for the entirely altruistic type, either. That was the case with Huntress, and their complicated relationship was scrutinized by fellow members of the Bat-Family at the time. However, that has nothing on what went down in 2001’s Nightwing #52 by Chuck Dixon, Greg Land, Drew Geraci, Patricia Mulvihill, Jamison and John Costanza. In that issue, Bruce Wayne’s former sidekick had a brief fling with his mentor’s longtime love interest, Catwoman.
This whirlwind romance began when Selina Kyle became fed up with Gotham. With the Dark Knight still in her head, she decided to take her mind off her hopeless romance with a simple heist. Blüdhaven seemed like the perfect place. There was no hope of Batman showing up to stop her there and a precious diamond up for grabs, making it a great way to forget her troubles. What she didn’t count on was the city’s guardian protector being the original partner of the person she was trying to forget.
At first, Nightwing and Catwoman come to blows, with the former believing she’s been hired by the diamond’s owner for an insurance scam. He quickly deduces she’s working alone when the two are almost caught by those who were actually hired to steal the diamond. The two hide in the rafters to avoid detection, in a very cramped and intimate way.
Selina, seeing an opportunity to make Batman jealous, decides to play this tense situation to her advantage. Forcing Nightwing to save her from “falling” places the hero of Blüdhaven firmly on top of her, giving her an opportunity to kiss him. Even after they scandalously lock lips, Nightwing remains focused on the mission. Catwoman starts pulling out all the stops to seduce him but nothing seems to work. Despite this, they work well together. The famed thief even notes that the hero moves just like his mentor, sometimes even better.
With the diamond returned and their business complete, the two discuss what went down on a nearby rooftop. Catwoman asks Nightwing not to mention their kiss to Batman, at which point he realizes what she’s been trying to do this whole time. Catching on that the Cat wants him to tell his mentor everything, to make him jealous, Dick bursts out in laughter. This results in him earning a quick punch in the face, as Selina slinks off into the night.
Either Nightwing really didn’t tell Batman what happened or neither of them thought it was a big deal. The flirtatious encounter never came up again and certainly never caused any tension between the two, far from it. In the 2003 story “Hush”, Nightwing is the one who encourages Batman to reveal his secret identity to his longtime love. In the lead up to their doomed wedding in DC Rebirth, Dick was a serious contender for Bruce’s best man. So whilst these two were a disastrous match, in the end, it was nothing too serious and no harm was done.