Superheroes often have convoluted love lives, and Nightwing is no exception. Dick Grayson often finds himself navigating a love triangle between his closest friends and allies, Starfire and Barbara Gordon's Batgirl. While his affections tend to fluctuate depending on the iteration and story, Nightwing’s love triangle is functionally settled by his original, longest running crush.
Dick Grayson began his superhero career as Batman’s sidekick, Robin. During his time in Gotham, he fought alongside the Caped Crusader, Commissioner Gordon, and eventually, Gordon's daughter Barbara. Dick cultivated a budding friendship with Barbara, but eventually left for college and to become Nightwing. In his time away from Gotham, Nightwing assembled the Teen Titans, and fell head-over-heels for Starfire. Over the years, Nightwing has admitted he'll always love both, with fans disagreeing about which relationship is the character's most desirable endgame.
In Nightwing: Secrets Files and Origins' 'Orange You Glad I Didn't Say Banana?' from Devin Grayson and Brian Stelfreeze, DC provides a lot of insight into Nightwing’s backstory and character, Nightwing and Batgirl reminisce about different formative experiences, and memories from their childhood. As they converse, Barbara shifts the topic of discussion to romance, and asks Dick about his first crush, running through the list of Dick’s romantic entanglements, including Donna Troy and Starfire. As Barbara continues to incorrectly guess the identity of Nightwing’s first crush, the former Boy-Wonder makes it clear it was her.
Nightwing’s affections tend to wander as his narratives evolve, sometimes even making him seem careless with the hearts of those he loves. While at one time it appeared that Starfire was definitively Dick’s happily ever after - the self-possessed hero he met after breaking free of Batman's shadow - the revelation that Batgirl was Dick's very first crush adds a sense of history to their relationship that's hard to beat, and indeed they're currently dating in his ongoing comics. It makes sense, given that Batgirl and Nightwing have a very natural chemistry, shared Gotham roots, and a healthy power balance in their relationship (something that even The Boys called out as an issue between Nightwing and Starfire.) Their dynamic is rock solid, working seamlessly regardless of whether Barbara is donning the Batgirl or Orcale persona.
Back when Nightwing's main goal in life was to establish himself in Gotham, his relationship with Starfire was associated with his growth as a person. However, as he's undeniably become a hero in his own right and buried the hatchet with Batman, Dick has come to look back on the past more favorably, and his older ties have only increased in significance. The fact that every other love interest is the wrong answer to his first crush and Batgirl is the right one hammers home that their bond is genuinely undying, and will ultimately be the one that lasts.
Many superheroes have complicated personal relationships, and Dick Grayson’s decades-spanning love triangle with Batgirl and Starfire is a prime example of an unavoidable issue with long-running, multi-authored serialized narratives. With a tangled web of infatuations, marriages, and flings, Nightwing’s romantic history seems nigh incomprehensible. However, with their early relationship cutting through the noise, it seems like the definitive answer to the ever-changing Nightwing love saga is his original flame, and one of his longest-running allies, Barbara Gordon