Quick Links

Bruce Wayne's billionaire playboy lifestyle and Batman's crime-fighting heroics have introduced a few femme fatales to the Dark Knight's life. In fact, most of Batman's most important and powerful romantic connections have been with the supervillains in his extensive rogues' gallery.

RELATED: 10 Worst Things About Dating Batman

Throughout the character's long comic, film, and TV history, Batman has often turned to the female villains populating Gotham City to fill the romantic void in his bat-shaped heart. Although most of Gotham's Most Eligible Vigilante's relationships have ended in tragedy, they represent how both the hero and his villains long for some semblance of a meaningful, normal love life.

Updated on February 10, 2023, by Scoot Allan: The new DCU slate announcement led fans to begin speculating on which direction The Batman: Part II and The Brave and the Bold will take the Dark Knight and his rogues' gallery. While Talia al Ghul and Catwoman are famous examples, it might shock some fans to learn that Batman has forged romantic connections with quite a few villains over the years.

Villains Batman Has Romanced

Catwoman

Batman and Catwoman kissing while dressed in a formal wedding dress

Catwoman is one of the Caped Crusader's most enduring, on-again, off-again romances. Catwoman's mainstream comic debut occurred in Bill Finger and Bob Kane's Batman #1. Since then, Selina Kyle has become Batman's greatest love interest. Their earliest stories explored different emotional and entertaining "what ifs" for the timeless characters.

Earth-Two's classic incarnation of Batman and Catwoman married and raised a daughter, Helena, who became the Huntress. Jeph Loeb and Jim Lee's Batman: Hush solidified their modern relationship when Bruce revealed his secret identity to Selina. Batman and Catwoman's relationship deepened over the years and they almost married recently, though took a break to work on themselves first.

Talia Al Ghul

Talia al Ghul with her father Ra's and beloved Batman in the background

The other great love of Batman's life first appeared in Dennis O'Neil and Bob Brown's Detective Comics #411. Talia al Ghul is the deadly and cunning daughter of Ra's al Ghul. He chose Batman as his successor as the head of the League of Assassins and hoped he would wed his daughter. Talia and Batman developed feelings for each other but were torn apart by their missions.

Talia struggled with remaining loyal to her father's mission or embracing Batman's moral crusade against crime in Gotham. However, in Mike W. Barr and Jerry Bingham's Son of the Demon, she drugged and assaulted Batman, leading to the birth of their son, Damian Wayne. Damian grew up to join his father as Robin, embracing his father's philosophy, which further strained the relationship between Batman and Talia.

Jillian Maxwell

Jillian Maxwell marrying Batman in Legends of the Dark Knight Halloween Special

Due to the lingering disorienting effects of Scarecrow's fear toxin, Bruce Wayne fell pretty hard for Jillian Maxwell in the pages of Jeph Loeb and Tim Sale's Batman: Legends of the Dark Knight Halloween Special #1. Unfortunately for Bruce, Jillian was only really gunning for the billionaire playboy's immense fortune.

RELATED: 13 DC Characters Batman Has Never Beat In A Fight

Fortunately for Bruce, Alfred discovered Miss Maxwell's violent penchant for marrying, murdering, and making off with her rich victims' money and intervened. Even when Bruce tried to fall for a 'good one,' she turned out to be evil. At least Jillian was only a normal, greedy con artist and not a powerful and deadly supervillain. It's almost progress.

Poison Ivy

Poison Ivy with Batman in the New 52

The environmentally-themed DC villain Poison Ivy uses her powers to control anyone in her way, including Batman. Their attraction is more driven by the uncontrollable lust she inflicts on her victims than true romantic feelings. However, Batman and Poison Ivy have displayed true compassion for each other over the years as well.

Unfortunately, Poison Ivy has been chemically seducing Batman since Robert Kanigher and Sheldon Moldoff's Batman #181. Tim Sale created a visually intriguing and horrifying version of Ivy's methods in Jeph Loeb's The Long Halloween. Most of their stories follow the patterns set up by their first few encounters, though their relationship has grown over the years.

Nocturna

Nocturna kissing Batman in the comics

Natalia Knight first appeared in Detective Comics #529 by Doug Moench, Don Newton, and Gene Colan in 1983. An accident bleached her skin completely white, making her incredibly sensitive to light, and she became Nocturna, Mistress of the Night. Nocturna also used a perfume that rendered her irresistible to others, making her feel more than a little bit like Poison Ivy's dark-dwelling cousin.

Natalia joined her brother Anton in a series of crimes that caught Batman's attention. He was immediately attracted to her and got involved with the villain, both as Bruce Wayne and Batman. Nocturna successfully battled Bruce for custody of Jason Todd as part of a scheme to force him to marry her after she learned his secret identity. However, he rejected her and she disappeared.

Jezebel Jet

Jezebel Jet taunting Batman in the Batman R.I.P. storyline

Jezebel Jet's relationship with Bruce Wayne was complicated, to say the least. Creator Grant Morrison gave Jezebel a very tragic past in the Batman: R.I.P. arc that set her up as the ruler of the small African nation, Mtamba. She met Bruce at a fundraiser and they quickly fell in love. After he intercepted an attempt on her life, she realized that Bruce Wayne was actually Batman.

RELATED: 25 Most Iconic Batman Quotes Ever, Ranked

However, during Batman's climactic battle with the Joker at Arkham Asylum, Jezebel revealed her secret identity as an agent of the Black Glove. Batman responded by revealing he'd known about her ties to the secret society all along. Needless to say, their relationship didn't last. Talia al Ghul, who had been keeping tabs on their budding and mutually duplicitous romance, later had Jezebel Jet killed.

The Phantasm

Phantasm from the comics with the animated Bruce and Andrea Beaumont kissing in the background

Andrea Beaumont played a prominent role in Bruce Wayne's love life in the critically acclaimed animated film Batman: Mask of the Phantasm before later appearing in DC Black Label's Batman/Catwoman. Their love was another heartbreaking entry in the Dark Knight's romantic annals. In the film, Andrea and Bruce fell in love before Bruce became Batman and were even engaged.

Unfortunately, Andrea left the country after her father double-crossed Gotham City's underworld. Years later, she mysteriously reappeared in Bruce Wayne's life. The romantic reunion was short-lived, however. Her father had been murdered by the mob and she became the murderous Phantasm to destroy Gotham's elite gangsters. Bruce and Andrea were too much alike, and she vanished from Batman's life.

Ten From The Royal Flush Gang

Melanie Walker as Ten from the Royal Flush Gang in Batman Beyond

Others who have taken up Batman's mantle haven't been spared the heartbreak that came with it. Terry McGinnis proved himself as the Caped Crusader in the DCAU's Batman Beyond. He fell for Melanie Walker after sharing an unexpected kiss and they agreed to meet up again for a date. Unfortunately, a happy ending wasn't in the cards for the new lovers.

Melanie's alter ego was Ten in the supervillainous crime family, The Royal Flush Gang. Terry discovered her secret identity and put a stop to their relationship before it really started. Batman's influence ultimately helped Melanie reform and leave her villainous family and life of crime for good.

Thanatos

Sophia Santos disguised as Lina Muller with Bruce Wayne and Santos as Thanatos with the Death-Heads Gang

Sophia Santos was the costumed leader of the Death's-Head terrorist group who first appeared in Gerry Conway and John Calnan's Batman #305. She organized a string of attempted bombings in Gotham City as Thanatos and also posed as news reporter Lina Muller to lure millionaires to Gotham Isle

RELATED: Batman's Greatest Secret Weapons, Ranked

Once there, "Muller" used a device called the "Fortu-Tron" to sap her victims' common sense so they would gamble away the entirety of their trust funds. Bruce lost some money to Sophia's beauty and wiles (and the Fortu-Tron), but Batman won in the end. He outsmarted Sophia, uncovered her identity as Thanatos, and took down the Death's-Head organization.

Penumbra

Penumbra vs Batman and Catwoman

The New 52's Detective Comics #0 by Gregg Hurwitz, Tony S. Daniel, and Pere Pérez introduced Penumbra, a particularly deadly DC assassin. Bruce Wayne fell in love with an unassuming girl named "Mio" while studying under martial arts master Shihan Matsuda. One night, Bruce fought off an assassin hired by Matsuda's wife to kill her own husband.

Bruce discovered that Mio was actually the assassin, trained by one of Batman's most iconic enemies, Ra's al Ghul. She later returned to Gotham City as a member of the League of Assassins named Penumbra. Batman discovered her identity and tried to reason with the Mio he'd loved, but she escaped to face her punishment for failing her mission.

Queen Bee

Batman spanking Marcia Monroe with Queen Bee saluting split image

Marcia Monroe was a spoiled debutante and thrill seeker who debuted in Bob Haney and Win Mortimer's Brave and the Bold #64. She enjoyed putting herself in mortal danger for publicity, distracting Batman away from real crime. After she plummeted off a bridge, he first saved her then spanked her in public.

In reality, this was both inappropriate and humiliating, but thanks to comic book logic, Monroe fell in love with the Dark Knight. They became a couple after she began shadowing his nighty crime-fighting, but she disappeared. She returned to Gotham as the first Queen Bee and led the crime syndicate, CYCLOPS. She double-crossed Batman and tried to steal some precious gems before vanishing once more.

Martha Wayne's Joker

Flashpoint Batman and Joker holding hands

In the Flashpoint timeline, Joe Chill murdered Bruce Wayne instead of his parents. Broken by the loss, Bruce's father Thomas Wayne became a far more brutal and tortured Batman. However, Martha Wayne's fate was far worse. She tracked down Joe Chill, beat him to death with a hammer, and became the Flashpoint's version of the Joker.

RELATED: 10 Gadgets Batman Shouldn't Have Used

This Joker's gruesome accomplishments included kidnapping Harvey Dent's daughter and tricking Jim Gordon into shooting her before she murdered him. She ultimately took her own life when Thomas explained that they could rewrite the timeline, turning Bruce into Batman instead. There weren't many happy endings in the Flashpoint timeline.

Villains Batman Should Romance

White Rabbit

Jaina Hudson with Bruce Wayne and White Rabbit with Batman split image

White Rabbit took Bruce Wayne down the rabbit hole in her first appearance in David Finch's Batman: The Dark Knight #1. Jaina Hudson's unique powers allowed her to split herself into two separate bodies and personalities. She was another one of Gotham's wealthy socialites, which meant Bruce started flirting within seconds of laying eyes on her.

Batman later became acquainted with Jaina's White Rabbit persona when he attempted to stop a mass breakout at Arkham. White Rabbit enhanced criminals with drugs to cover her escape. However, she still came onto Batman during their confrontation. Batman and Bruce Wayne could live separate lives with Jaina Hudson and White Rabbit, which would at least keep things interesting.

Lady Shiva

Lady Shiva stands ready and awaits her opponent's next move.

Lady Shiva has always wavered between being an ally and an enemy of the Dark Knight. The two have clashed many times over the years. Lady Shiva is one of the most dangerous assassins in the world and a deadlier martial arts master than even Batman, but she also has a strong sense of honor and decency.

Lady Shiva's become more involved with Gotham City and the Bat Family over time. She even trained the third Robin, Tim Drake, and helped restore Batman's fighting edge after the Knightfall event. Batman and Lady Shiva could be a match made in DC heaven if she wasn't a killer and a Shiva redemption arc would be fascinating.

Harley Quinn

Harley Quinn kissing Batman

Dr. Harleen Quinzel first appeared as an original character in the acclaimed Batman: The Animated Series episode, "Joker's Favor." Her love affair with Joker was toxic and ended in both the animated series and the comics when she left him to join her BFF Poison Ivy as a crime-fighting duo and later, one of DC's best romantic couples.

Batman earned an unexpected kiss from Harley Quinn after he believed she was innocent in the Batman: The Animated Series episode "Harley's Holiday." She also fantasized about falling in love with Bruce Wayne in the Harley Quinn Valentine's Day Special one-shot. It's not clear how much of this attraction is one-sided but Harley can make anyone's life more interesting, even Batman's.

NEXT: 10 Batman Villains Who Could Have Been Great Heroes