He may have been trained by Batman, but Nightwing could teach the Dark Knight a thing or two about love. Over the decades as Robin or Nightwing, Dick Grayson has put his skills to the test in the bedroom with a number of different lovers. Heroes, villains, regular people, there have been a great number of Nightwing hookups.
Some of Grayson's romantic partners were brief affairs and others lasted for years. Some of them were innocent infatuations with kissing while others were passionate sex romps. There are even a couple disturbing sexual encounters, too. Just take a look at this list of the various Nightwing romantic relationships and sexual encounters.
Wow, who would've guessed you could get this far writing a Nightwing sex list without making a "Dick" joke? (Wait, does that count?)
One of the top two cited true loves of Dick Grayson is Barbara Gordon, a.k.a. Batgirl, a.k.a. Oracle. As youngsters, the two often paired together as students and partners of Batman which lead to casual flirting and teenage romance. Their on-again, off-again relationship blossomed into more adult encounters with the utility belts off as they grew up. The two even talked about getting married, but they ultimately remained apart.
Another top-cited Nightwing lover is his fellow Teen Titans teammate Starfire. During George Perez and Marv Wolfman's run on The New Teen Titans, Koriand'r and Dick Grayson became arguably the best sex-positive couple in all of comics. While the two considered marriage, they broke it off when Grayson knew deep down that he didn't completely love Kori. That said, they have still hooked up casually many times since then.
When Dick Grayson started his college studies at Hudson University, he met and dated a starry-eyed blonde named Lori Elton. The two were a couple within the pages of Detective Comics from 1975 through 1979, but Elton dumped Dick in favor of Dave Corby. Naturally, Corby turned out to be a costumed criminal... because comics.
When Grayson decided to fight crime in Blüdhaven, he rented an apartment and got into a brief affair with his landlord in Nightwing Vol. 2. While the two originally wanted to take their relationship to the next level, Dick was still drawn to Barbara Gordon. The two remained friends, but there's no way Dick got his security deposit back.