Let’s face it: Dick Grayson is a hero with a reputation for being a guy with a complicated and extremely active love life. That’s not to say he’s a womanizer, of course, but Nightwing’s romantic endeavors are part and parcel of who he is, so his status quo in the Rebirth DCU is really no different. Over the past year and a half, Rebirth's Nightwing, Birds of Prey and Batgirl have all taken swings at figuring out just who Dick is dating — only to come up with inconclusive answers.
Dick Grayson’s love life might be confusing and multifaceted, but Nightwing’s “Spyral” arc has shifted the focus of Dick’s affection back to one of his old flames: Helena Bertinelli, aka Huntress -- a dynamic that has continued to maintain focus even as the most current story arc, “Raptor’s Revenge,” has picked up. But while dating is never simple for superheroes, it’s always somehow even more complex for Nightwing.
Nightwing and Huntress Reborn
The Dick and Helena couple has recently pulled ahead as a definitive outlier in the world of Nightwing shipping. Strangely, it’s a pairing that only recently came into the spotlight after the New 52 in Tom King, Tim Seeley and Mikel Janin’s Grayson, where Dick met Helena for the first time since the reboot as a fellow member of Spyral. This specific incarnation of Helena wasn’t yet Huntress, but a headmistress-slash-spy called Matron who worked as Dick’s superior within the organization.
In Grayson, Dick and Helena maintained a contentious but flirty back-and-forth, but never going as far as to be overtly romantic. This, of course, is a staple of the Dick Grayson love story: Loosely defined liaisons that provide a lot of wiggle room across multiple books and stories. Dick and Helena may have never formally “dated” but the emphasis on their connection -- physical or otherwise -- was certainly there.
Prior to their New 52 relationship, however, Dick and Helena’s connection was relatively cursory. They met and hooked up back during No Man’s Land, the event that established Helena as a hero within Gotham City, but parted ways on bad terms shortly after. They never really reconnected after that, making the emphasis on pairing them post-Flashpoint both fresh and slightly non sequitur.
Rebirth kicked off with Dick and Helena parting ways yet again, albeit on much better terms. With Dick trading in his Spyral-branded Hypnos spy-tech for his blue-and-black costume once more, and Helena giving up her Matron title to claim her pre-New 52 Huntress moniker, there just wasn’t much that would keep them together -- that is, of course, until there was. Helena’s Rebirth road returned her to the Birds of Prey, which gained an ongoing series set in Gotham City. Dick spent the early days of Rebirth globetrotting before landing back in Blüdhaven for the first time since it’s Chemo-bomb destruction during Infinite Crisis in 2006. Given the proximity of their newfound homes, they were bound to cross paths.
And cross paths they did, but with one tiny complication. A new element had been added to the mix in the post-Rebirth world; upon his return to Blüdhaven, Dick began to date Shawn Tsang, a former villain turned social worker who went by the code name Defacer. An invention of Rebirth's Nightwing (albeit one based on, of all things, a Hostess cupcakes ad from the '70s), Shawn became the most recent in a long tradition of female side characters introduced in Dick’s ongoing stories with the initial pretext of being love interests. Unlike the majority of her forebearers, however, Shawn’s presence was actually consciously noted in other ongoing books when Dick would show up.
Helena and Dick’s reunion in Birds of Prey #8 came with the caveat that Dick was currently seeing someone else, which made things awkward — but not too awkward — between both Helena and Dick, and Dick and Barbara.
Right, there’s also the Barbara situation.