Dick Grayson's Love Interests
- Barbara Gordon: When Barbara started her career as Batgirl working with Batman and Robin, she and Dick began to grew closer time by time and eventually they began a romantic relationship. This relationship became a longtime on-and-off relationship continued even after Barbara's retirement. He at one point asked her to marry him, to which she accepted but called off feeling they weren't ready.
- In the movie Batman and Robin, Dick meets Barbara Wilson, Alfred's niece, who later becomes Batgirl. In the film they have the same relationship that Dick has with Barbara Gordon in the comics.
- In the most of the cartoon series such asYoung Justice and Batman the Animated Series, Dick meets Barbara Gordon, as Batgirl. Both were shown to have similar history as their comic versions. In the Batman series, the two have an on/off again relationship.
- Starfire: Having a longtime on-and-off again relationship with Dick Grayson during their time together in the Titans and Outsiders and beyond, the pair at one time almost married. Dick last wanted to keep Starfire as just a friend.
- Catalina Flores: A former FBI agent dressed as the Tarantula in order to battle the corrupt police officers and gangland criminals of the city. Dick did not approve of the more extreme measures she took. When investigating the murder of Delmore Redhorn Nightwing discovered the murderer was in fact Tarantula, and that she was working for his nemesis Blockbuster. She had also manipulated an encounter with Nightwing in such a manner that Barbara Gordon broke up with him. Nightwing was able to have Tarantula arrested for the murder of Redhorn but she was out on the streets soon enough, and when the battle between Nightwing and Blockbuster heated up, Tarantula involved herself and shot Blockbuster. Allowing Tarantula to kill Blockbuster caused Nightwing to go through what appears to have been essentially a nervous breakdown, and Tarantula took advantage of his near catatonic state to have sex with him. During the following period of time, she ran off with him and attempted to establish a relationship. After a while, Nightwing came to his senses and turned himself in for the murder of Blockbuster. He was acquitted, however, and worked to bring in Tarantula, who was sent to jail.
- Helena Bertinelli: Dick and Helena had a one night stand while out patrolling together, Dick wanted to start a serious relationship but Helena refused, since then the two have maintained a personal and professional friendship together.
- Bridget Clancy:Bridget Clancy was Dick Grayson's superintendent when he moved to Bludhaven. The two of them shared a romantic interest, but it never developed into anything. She is Asian in appearance, but has a Scottish accent.
- Emily Washburn: Emily was a young woman in Gotham City who in three years time had lost three husbands to freak accidents. Nightwing believed she was a black widow and decided to stop her from killing any more men. Thinking he could be her next target, he approached her in his civilian identity of Dick Grayson. They pair became close and Dick proposed. The two were wed in a fake ceremony that Dick staged. During their honeymoon in Hawaii, Dick and Emily ran into Emily's best friend Annelise. Annelise attempted to kill Dick but he was able to overpower her. It turned out that Annelise was attempting to punish Emily by killing any man she fell in love with. Dick learned that Emily's father had gotten Annelise's father arrested and Annelise was trying to get revenge. After Annelise's arrest, Dick revealed his plan to Emily. She was upset that Dick deceived her but grateful that he had cleared her name. Dick then offered to make a life with Emily and her son but she declined stating that Dick had other secrets he couldn't share with her.
- Raya Vestri: Raya was a childhood friend to Dick at Haly's Circus as well as his first crush, the two began dating even though Raya at first wanted only a sexual relationship.
- Cheyenne Freemont: Cheyenne was a fashion designer and at some time a model who first met Dick when they had a one night stand together. The two formed a "no strings attached" relationship for a while. The relationship didn't last long due to Cheyenne wanting to start life for herself and to avoid the metahuman brothers tracking her.
- Selina Kyle (Catwoman): Though they have never shared a romances in the comics, they did have a flirtatious team-up in the Batman: The Animated Series episode, You Scratch My Back. Where Catwoman tried, unsuccessfully, to get Nightwing to run away with her after stealing a famed emerald from Argentina. This episode marks the only time in Batman history where Catwoman & Nightwing shared a kiss.
- Zatanna: In the new series Young Justice, Dick flirts with Zatanna when they go on a mission to rescue Red Tornado after she is introduced to the team by her father Zatara. In a latter episode Dick explains how he got a magical necklace from Zantana without her asking questions he expains that they have a 'special relationship'
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