Indeed, for the rest of the 1980s that relationship was one of the tent poles of the Titans franchise—which meant Marv Wolfman and his artists were constantly shaking it to make readers worry. Kory contracted a political marriage for the sake of her home planet, and Dick couldn’t handle it. Teammate Raven had sexual fantasies about Dick, and Kory could handle it. A freedom fighter from an alternate future disguised herself as Kory to have sex with Dick.
The relationship endured until New Titans, #100, when Dick and Kory tried to get married and everything went horribly, horribly wrong. Dick and Kory broke up, and that Titans team itself went separate ways—which just shows how much of a tent pole it was.
That left Dick Grayson unattached for the first time in years. He kept busy being Batman for a while, but then DC’s writers happily seized the chance to use “Dick has a new girlfriend” as the starting-point for stories.
Meanwhile, the internet enabled fanfiction to spread, and that area of writing has never been bound by what official continuities say about heroes’ love lives. As a result, Dick Grayson became a “fandom bicycle” on which everyone got a ride. TV Tropes lists him as DC’s top “Launcher of a Thousand ’Ships,” saying: “It's a running gag in the DC Universe that virtually every female that comes in contact with Nightwing falls in love with him.” In fanfiction, that group expands to include every male.
Despite Dick being a symbol of sexual appeal, however, his romantic/sexual activity within the comics was exaggerated. Here’s a conversation on the topic between Dick and Tim Drake, his successor as Robin, in Nightwing, #25 (dated October 1998, script by Chuck Dixon, art by Scott McDaniel). The boys are, naturally, standing on the back of a freight train while blindfolded—Dick’s told Tim this is good training. Tim manages to say the only thing that can throw Dick off balance.
girlfriend who’s not an “Afterschool Special,” knowing that won’t happen. Tim responds by showing off how much of a Dick Grayson fan he is.
As Dick reminds Tim, he and Donna Troy never “really dated.” They never dated at all. Wolfman did propose to “have very slowly had Dick and Donna get together,” “if only for them to see that they were too similar to be together.” But that never happened.
Miggie Webster appeared in the Nightwing miniseries by Dennis O’Neil and Greg Land. Dick was apparently depressed at the time—or maybe just weighed down by his hair. In any event, he became briefly infatuated with Miggie because he thought she represented a normal, happy family life—only to see her kill her abusive father. And as far as I can tell, they never even went on a date.
Emily Washburn married Dick in Nightwing Annual, #1 (cover shown above). That was part of a 1997 DC tribute to pulp fiction, and the story was a James M. Cain-style take on a murderous marriage. Dick married Emily as part of his investigation. After he identified the killer, he offered to remain her husband and help raise her son—again with the monogamous values!—but she declined. It’s unclear whether the marriage was consummated, but given scripter Devin Grayson’s take on Dick as a very physical and open person, it probably was.
Meanwhile, in 1996 DC launched the Nightwing series written by Dixon. Among its subplots was Dick’s friendship—or would it be something more?—with the superintendent of his apartment building in Blüdhaven, Bridget Clancy. Dixon was a master at playing out conflicts over many issues, but this relationship never reached the level of dating.
Instead, at the time of this train-top conversation, Dixon was gradually moving Dick toward a second serious, multi-year relationship: with Barbara Gordon, daughter of the Gotham police commissioner, former Batgirl, and at that time Oracle. Dick had shown interest in her in the 1970s, but fans then pointed out that she was several years older than he. At the time of this issue, Nightwing, #25, it was still unclear whether they would become an item.
Thus, of the six women Tim reeled off, Dick had actually had serious and/or sexual relationships with only two, and in one of those (Emily Washburn) he was working on a case. That exchange thus leaves a misleading impression.
But in that miniseries Dick is looking for something long-lasting. (He’s evidently drawn to strong women who need rescuing.) The story ends with Helena seeing the chemistry between him and Barbara and chuckling that they don’t notice it themselves. In other words, even this example of Dick having a sexual fling points to him as a man seeking a committed love.
From the No Man’s Land crossover (1999) through Infinite Crisis (2006), Dick and Barbara were usually a couple. Since then, each new regular Nightwing scripter came up with a new love interest: a fashion designer, a criminal who lured a teen-aged Dick away from Wayne Manor, a librarian. Judd Winick has put him back in bed with Kory a couple of times. But only the unfortunate Nightwing Annual, #2, portrayed him as anything other than a one-woman man.