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?)
Huntress and Nightwing had a brief tumble together within the pages of the Nightwing: Huntress limited series as the two teamed up to fight the mafia. It was later revealed that Huntress partially seduced Dick in order to get on the good side of Batman and the Bat Family. Oof. That's hurtful.
Catalina Flores debuted in Nightwing #71 and caused him nothing but trouble. She balanced on the line between hero and villain, but Nightwing took her under his wing due to her great potential as a crimefighter. Tarantula pined for Nightwing the entire time, but while Dick cared for her, he had no real romantic interest.
The reason Tarantula makes this list is a dubious one, to put it lightly. After Nightwing was in a physically and mentally weakened state in Nightwing #93, Tarantula took advantage of him and had sex with him on a rooftop. Grayson protested and was in deep shock during the sexual encounter, leaving many fans believing that Nightwing was raped because he did not verbally consent.
Cheyenne was the daughter of two metahumans and was content to live the quiet life of a clothing designer but was inspired by Nightwing to use her budding telekinetic powers to fight crime. She even donned an outfit that was inspired by Nightwing's costume. The two had at least one sexual encounter, but didn't pursue the relationship further.
When Dick Grayson had a falling out with Batman as a teen, he fell into the arms of Liu. Liu was his first love and took Grayson's virginity. Sadly, Liu only slept with Grayson in order to use his connection to Bruce Wayne and access Wayne Tech. This betrayal gave Dick a bunch of psychological hang-ups regarding his love life, including his distrust and unwillingness to fully commit to his sexual partners.