Over the years,Nightwing has been in all sorts of different relationships, all of which seemed doomed to fail. After graduating from his role as Robin the Boy Wonder, Dick Grayson surged in popularity. Since Nightwing's debut inTales of the Teen Titans #44 by Marv Wolfman and George Pérez, the character has stepped out ofBatman’s shadow and carved his own path.
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Dick is as much of a playboy as his mentor, Bruce Wayne. Dick has shared notable romances with characters like Starfire,Batgirl, and Huntress, but he also shared relationships with lesser-known characters who impacted Dick's life in significant ways.
Updated on April 13, 2023, by Scoot Allan: Many comic book fans are familiar with Dick Grayson's longest-lasting relationships, but there are plenty of other women in Nightwing's life. After working as a secret agent, then returning to Blüdhaven, Nightwing has established relationships with more obscure characters that some comic readers may be unaware of.
13 Liu
First Appearance:Nightwing #133 (2007) by Marv Wolfman, Jamal Igle, Keith Champagne & Edgar Delgado

For those who are unfamiliar, Liu was actually one of the first women Dick Grayson ever truly loved. When he was a teenager, the two became closely involved, and Dick even lost his virginity to her. Unfortunately, Liu had ulterior motives.
She was basically using Dick for his connections to Bruce Wayne. While she was his first major heartbreak, there wasn’t much else that was special about Liu. While she may have caused some emotional damage, the former Boy Wonder has definitely had some much stronger relationships since.
12 Bat-Girl
First Appearance:Batman #139 (1961) by Bill Finger, Sheldon Moldoff, & Stan Starkman

Dick Grayson was one of the first ofDC's new generation of heroes, but he definitely wasn't the last. As Robin, he inspired a few other young heroes to start their own careers as costumed crimefighters. Bette Kane made her Pre-Crisis debut as Bat-Girl alongside her aunt, Kathy Kane/Batwoman.
While most fans are aware of Nightwing's long-time relationship with Barbara Gordon/Batgirl, they might not remember his short-lived and mostly one-sided romance with Bette Kane in the Pre-Crisis continuity. TheCrisis on Infinite Earths erased this version of the character, and the modern take on Bette Kane/Flamebird never rekindled the romance with Nightwing.
11 Terri Bergstrom
First Appearance:Batman #230 (1971), by Frank Robbins, Irv Novick, Dick Giordano, & John Costanza

Another of Dick Grayson's earliest romances appeared during his time at university. Her name was Terri Bergstrom, and she was actually the cousin of Robin'sTeen Titans teammate, Lillith Clay/Omen. However, Grayson actually met Terri at Hudson University, and they were initially unaware of her familial connection.
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Much like her cousin, Terri had undeveloped psychic abilities that she used to help Robin on more than one occasion. Unfortunately, her connection to her cousin left her vulnerable to demonic forces, so they kept their distance from each other to keep Terri safe. This also led to the end of her relationship with Dick Grayson and she soon disappeared from continuity.
10 Raven
First Appearance:DC Comics Presents #26 (1980) by Marv Wolfman, George Pérez, Dick Giordano & Adrienne Roy
Though the two are typically associated as teammates, there was a brief time when Nightwing and Raven actually had a romantic connection. Raven grew more in touch with her emotions, and her relationship with theTeen Titans' best leader became increasingly complicated.
In actuality, the two never did more than share a kiss. However, Raven’s feelings definitely put some interesting imagery into Dick’s head. In the end, the two decided that they were much better as teammates and nothing more. Their romance has practically been forgotten, which is probably for the best as the majority of fans feel the Titans teammate Dick should end up with is Starfire.
9 Tarantula
First Appearance:Nightwing #71 (2002) by Devin Grayson, Rick Leonardi, Jesse Delperdang, Gregory Wright & Digital Chameleon

Nightwing’s relationship with Tarantula is still one of the most infamous moments in the character’s history. Acting as more of an anti-hero, Nightwing paired up with Catalina Flores with the hopes of getting her to become more heroic. After spending so much time together, Tarantula eventually developed feelings for him, though Nightwing never really reciprocated them.
Unfortunately, Tarantula definitely took things too far when she took advantage of Nightwing while he was in a weakened state. Nightwing's time with Tarantula is a chapter that fans don't want DC to revisit, especially with Dick's newfound success in and out of costume inTom Taylor'sNightwing series.
8 Cheyenne Freemont
First Appearance:Nightwing #118 (2006) by Bruce Jones, Joe Dodd, BIT & Javier Rodriguez

Despite a few small appearances, Cheyenne Freemont actually showed a lot of potential as a character. Even though she had metahuman abilities of her own, Cheyenne chose to keep them a secret, not even using them under the guise of an alter-ego. Shortly after meeting Dick, however, he would convince her to give heroism a try.
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Debuting a sleek spin on the Nightwing costume, Cheyenne actually made for a pretty interesting hero, especially with her telekinetic abilities. Though she disappeared shortly afterward, her powers and affiliation with the Nightwing persona made her more intriguing than some of Dick's other romantic attachments.
7 Sonia Zucco
First Appearance:Detective Comics #879 (2011) by Scott Snyder, Jock & David Baron

Known also as Sonia Branch, this relationship of Dick’s proved to be incredibly complicated. Sonia’s father is Tony Zucco, the mobster who killed Dick’s parents at Haly's Circus. Though Sonia had done a lot over the years to distinguish herself from her father, her relationship with Dick never really took off given her family ties.
Of course, things were fine between them until Dick learned about her connection to Zucco, but that doesn’t make the situation any less complicated. While there was a lot of potential for them at first, Sonia reminded Dick of one of the darkest moments in his life.Nightwing has improved his character a lot over the years, and staying with Sonia might have undone some of his growth.
6 Lori Elton
First Appearance:Detective Comics #450 (1975) by Elliot S. Maggin & Walt Simonson

When Dick Grayson started college, Lori Elton was one of the first women to catch his eye. The two met on campus and were actually romantically involved for several years within the comics. Considering how long they were together, it is astounding that so few people have actually heard of her.
Over the course of their relationship, Lori and Dick definitely experienced rough patches. Eventually, Lori started dating a villain known as The Raven and tried to reconcile with Dick after the fact, but their relationship essentially ended there.
5 Deborah Poulos
First Appearance:Nightwing #140 (2008) by Peter Tomasi, Rags Morales, Michael Bair & Edgar Delgado

Few readers have likely heard of Deborah Poulos, even though things actually got pretty serious between her and Dick Grayson. Towards the end of their relationship, Deborah actually asked Dick to move to California with her, showing just how much faith she had in their relationship.
Despite this touching moment, Dick had to decline due to his duties as Nightwing, and the character disappeared. Deborah didn’t exactly stand out from the other women in Dick’s life. Her brief appearances have been largely overshadowed byNightwing's more popular relationships with Starfire and Barbara Gordon.
4 Shawn Tsang
First Appearance:Nightwing #10 (2017) by Tim Seeley, Marcus To & Chris Sotomayor

Shawn Tsang appeared in one of the first few arcs of theNightwing Rebirth series. Unfortunately, despite being so new, the character has already faded into DC's background. However, that didn’t stop her from being one of the more genuine relationships in Nightwing’s life.
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Even after Dick learned she was a former masked criminal, her relationship with Dick continued to be one of the highlights of the series. Though things didn’t work out between the two of them, Shawn still helped give theNightwing series an incredibly strong start. To this day,Nightwing has remained one of the most consistent books since the Rebirth era.




