Batman's legal ward, Dick Grayson became the first Robin before he took on his current role as Nightwing. Not only did he develop a reputation as a great hero, but he turned out to be quite the ladies' man. His captivating features, muscular build, and compassionate heart helped him charm ladies with ease.
Many fans consider Barbara Gordon/Batgirl to be Nightwing's greatest love. The two have been through a number of trials but have consistently emerged as a fan favorite couple. Fans also cherish the great love between Starfire and Dick Grayson, but he's enjoyed a few other high-profile romances as well.
Updated on August 7, 2022 by Scoot Allan: Love has been in the air in recent issues of Tom Taylor and Bruno Redondo's Nightwing ongoing series. Dick Grayson and one of his greatest loves have reunited after years apart. Of course, Grayson spent most of their time apart dating other women and living up to his reputation as one of DC's best charmers. There are a few of his past girlfriends who got close enough to learn his greatest secret, but most were left to wonder "who is Nightwing?"
13 Raya Vestri
First Appearance: Nightwing (Vol. 3) #1, By Writer Kyle Higgins, Penciler Eddy Barrows, Inkers J.P. Mayer, Colorist Rod Reis, And Letterer Carlos M. Mangual
Raya Vestri and Dick Grayson go back a long way. They knew each other when they were young, during their days at Haly's Circus. Raya and Dick felt mutually attracted to each other, but the loss of Dick Grayson's parents led to their separation. They reunited years later when Dick was Nightwing and Raya was performing at Haly's Circus.
Grayson inherited the deed to Haly's Circus, and he had a one-night fling with Raya. However, she quickly ended things. Grayson soon learned Raya was working with another old acquaintance who became the assassin Saiko. Her attempts to get Grayson killed led to her incarceration. In an attempt to hurt Nightwing, The Joker killed Raya with his venom.
12 Lori Elton
First Appearance: Detective Comics (Vol. 1) #450, By Writer Elliot S. Maggin, Penciler/Inker Walt Simonson, And Letterer Ben Oda
Before Lori Elton dated Dick Grayson, she went out with Desmond Mallard at Hudson University. Desmond was the most sought-after student at Hudson until a football accident scarred him for life. Struggling with his new reality, he turned to a life of crime and took the name, "Scar." Dating Desmond was only the beginning of Lori's tumultuous love life.
Lori went from dating a criminal who tried to pour acid on her face to dating the heroic Dick Grayson. However, their relationship was brief and ended after their college classmate, Herbie Agar, was murdered in front of their eyes. Lori didn't understand why Dick was so interested in finding the killer. Finding his behavior weird, she ended their relationship.
11 Terri Bergstrom
First Appearance: Batman (Vol. 1) #230, By Writer Frank Robbins, Penciler Irv Novick, Inker Dick Giordano, And Letterer John Costanza
Terri Bergstrom and Dick Grayson attended Hudson University together, and she had psychic powers that Dick discovered on their first date. Terri eventually met with Robin upstate and helped him solve a few cases with her telepathy and telekinesis. She was also the distant cousin of Lilith Clay/Omen, a member of the Teen Titans.
Terri's connection to the Titans led to her becoming possessed by demons cultists had summoned. Terri's powers manifested intensely because of her proximity to her cousin, so they stayed away from each other to stop the threat of another demonic possession. The Crisis on Infinite Earths event later erased Terri Bergstrom from DC's continuity.
10 Bette Kane (Pre-Crisis)
First Appearance: Batman (Vol. 1) #139, By Writer Bill Finger, Penciler/Inker Sheldon Moldoff, And Letterer Stan Starkman
Bette Kane was the niece of DC's original Batwoman, Kathy Kane. Bette followed in her aunt's footsteps to become the very first Bat-Girl in the Pre-Crisis continuity. She was originally created to be Dick Grayson's love interest during a period when creators worried about the appearance of Batman and Robin's relationship. Bette only appeared with the Bat Family for a short period.
The post-Crisis continuity reintroduced Bette as Flamebird, where she fought alongside her idol, Dick Grayson, in his Nightwing role. The two heroes never became romantically involved in the modern era. Bette eventually adopted the new identity of Hawkfire and briefly trained alongside the modern Batwoman, Kate Kane.
9 Bea Bennett
First Appearance: Nightwing (Vol. 4) #50, By Writer Benjamin Percy; Pencilers/Inkers Travis Moore, Chris Mooneyham, & Klaus Janson; Colorists Tamra Bonvillain, Nick Filardi, & John Kalisz; And Letterer Carlos M. Mangual
One of Dick Grayson's best girlfriends didn't technically date Dick Grayson at first. She first met Dick when he was recovering from a headshot from KGBeast. He had lost all of his memories and began calling himself Ric. Bea was a volunteer at a local homeless shelter who offered Ric a room in her apartment building.
The pair eventually grew closer, and Bea helped Ric start down a new path in his life. Ric had abandoned his life as Nightwing, although he began helping others in a new vigilante identity. Bea proved instrumental in helping free Ric from The Joker's mental control during the Joker War. Even though she helped him regain his memories as Dick Grayson, he ended the relationship to protect her.
8 Helena Bertinelli
First Appearance: Huntress (Vol. 1) #1, By Writer Joey Cavalieri, Penciler Joe Staton, Inkers Dick Giordano & Bruce D. Patterson, Colorist Nansi Hoolahan, And Letterer Albert DeGuzman
Nightwing found himself in a brief relationship with Helena Bertinelli, better known as Huntress. In The New 52: Futures End continuity, fans learned Grayson and Bertinelli had been living together as a couple for many years. In the main continuity, however, Nightwing and Huntress's relationship only went as far as a one-night stand.
Both of them were young and working on a case alone, and Dick and Helena briefly found solace in each other's company. However, Huntress had a hidden motive in her attempts to get close to Nightwing, wanting to work her way into the Bat Family's inner circle. The modern version of Helena Bertinelli and Grayson briefly engaged in a romantic relationship, but it was fairly short-lived.
7 Shawn Tsang
First Appearance: Nightwing (Vol. 4) #10, By Writer Tim Seeley, Penciler/Inker Marcus To, Colorist Chris Sotomayor, And Letterer Carlos M. Mangual
Dick Grayson returned to protect the city of Blüdhaven in the Rebirth era as Nightwing. One of his first missions back in the city had him attempting to clear the name of Shawn Tsang, a former supervillain known as the Defacer. She had a history with Batman and Robin during Dick Grayson's time in the role, but she had served her time.
Grayson and Tsang grew close and began dating. However, Tsang's distrust of superheroes continued to weigh on her. Deathwing kidnapped her before Professor Pyg almost turned her into a Dollotron. Tsang decided she still wanted to pursue a steady relationship with Grayson, but she caught him in an intimate moment with Huntress and left him.
6 Cheyenne Freemont
First Appearance: Nightwing (Vol. 2) #118 By Writer Bruce Jones, Penciler Joe Dodd, Inker BIT, Colorist Javier Rodriguez, And Letterer Pat Brosseau
Fans were first introduced to Cheyenne Freemont after she spent a night with Dick Grayson, following one of his patrols as Nightwing. She displayed powerful telekinetic abilities after a dangerous suitor attacked her. Jason Todd threatened her when trying to tarnish Nightwing's identity, but Grayson saved her, and their relationship deepened.
Freemont eventually learned of Grayson's identity as Nightwing, and Dick found out about her metahuman abilities. Grayson tried to inspire her to become a hero, but Freemont didn't want to live that lifestyle. She did don a new take on Nightwing's costume to help him rescue Jason Todd. However, she quickly abandoned her new identity, leaving Blüdhaven and Grayson.
5 Helena Wayne
First Appearance: All-Star Comics (Vol. 1) #69, By Writer Paul Levitz, Penciler Joe Staton, Inker Bob Layton, Colorist Liz Berube, And Letterer Ben Oda
Before Crisis on Infinite Earths reshaped the DC universe, the Dick Grayson of Earth 2 was initially implied to be a love interest of the first Huntress, Helena Wayne, who is the daughter of this world’s Batman and Catwoman. However, since Dick and Helena were both raised by Bruce Wayne, they essentially saw each other as siblings and never pursued a romantic relationship. Both characters ultimately gave their lives during Crisis after losing their world.
After Infinite Crisis restored the DC multiverse, new Earth-2 versions of Dick Grayson and Helena Wayne emerged and were confirmed to have mutual romantic feelings. However, they once again never got romantically involved. When the original pre-Crisis versions were revisited in Convergence: Detective Comics, they were shown to be living together, but the nature of their relationship was left ambiguous.
4 Bridget Clancy
First Appearance: Nightwing (Vol. 2) #2, By Writer Chuck Dixon, Penciler Scott McDaniel, Inker Karl Story, Colorist Roberta Tewe, And Letterer John Costanza
Dick Grayson moved out of Gotham City and Batman's shadow in order to strike out on his own. He found a new home in the troubled city of Blüdhaven and quickly started cleaning it up. He rented an apartment where he first met the building superintendent, Bridget Clancy. They clicked almost instantly and went on a couple of dates together.
The romance didn't ultimately go anywhere due to a resurgence in Grayson's romance with Barbara Gordon. However, they still shared a meaningful friendship. Dick even helped Clancy fulfill her dream of going to medical school by paying for her admission.
3 Zatanna
First Appearance: Hawkman (Vol. 1) #4, By Writer Gardner Fox, Penciler/Inker Murphy Anderson, And Letterer Gaspar Saladino
Zatanna is one of DC's most powerful magic users. Zatanna and Nightwing's relationship in the mainstream comic universe never became romantic. However, their animated Young Justice counterparts had a brief relationship. They flirted back and forth from the moment they first met. Dick and Zatanna even snuck a few kisses before they finally shared a passionate one.
Unfortunately, Dick and Zatanna weren't together when the Young Justice: Invasion storyline jumped ahead five years. Fans never learned why the two ended their relationship, but the two remained close friends. Grayson might be something of a ladies' man, but he almost always kept great friendships with his past lovers.
2 Starfire
First Appearance: DC Comics Presents (Vol. 1) #26, By Writer Marv Wolfman, Penciler George Pérez, Inker Dick Giordano, Colorist Adrienne Roy, And Letterer Ben Oda
A powerful alien from the planet Tamaran, Princess Koriand'r became known as Starfire. She had incredible superpowers such as flight, super strength, and the ability to project powerful bolts of energy known as starbolts. Starfire's greatest displays of power occurred during her time with New Teen Titans, where she first met Robin.
Starbolt learned English through a passionate kiss with young Dick Grayson, igniting the romance that would develop over the years. She remained an ongoing love interest of Dick Grayson's for decades. Nightwing and Starfire almost married, but the untimely interruption of a Trigon-possessed Raven ruined their wedding and stalled their romance.
1 Barbara Gordon
First Appearance: Detective Comics (Vol. 1) #359, By Writer Gardner Fox, Penciler Carmine Infantino, Inker Sid Greene, And Letterer Gaspar Saladino
Dick Grayson first met Barbara Gordon while he was Robin, but the attraction was almost immediate. They began working closely together as Batgirl and Robin, which developed into a close friendship. However, his relationship with Starfire kept them from getting together for years. Nightwing and Oracle finally got together, but it was short-lived due to ongoing hurdles.
Dick once proposed to Barbara by saying he wanted to become a better person for her. Barabara said yes, but they decided to take some time apart. That time apart lasted until they recently got back together in an official relationship. The fact they have achieved impressive feats both as Dick Grayson & Barbara Gordon and as Nightwing & Batgirl make them one of DC's best couples.