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The Date Knight: 12 Villains Batman Has Romanced (And 3 He Should)

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The Date Knight: 12 Villains Batman Has Romanced (And 3 He Should)

There aren’t many superheroes out there who get lucky as often as Batman does. Between Bruce Wayne’s billionaire playboy lifestyle and the Dark Knight’s crime-fighting heroics, femme fatales abound. In fact, most of Batman’s most important and powerful romantic connections have been with the supervillains of his extensive rogues gallery. The Caped Crusader has a busy schedule, so it’s not rare to find him mixing business with pleasure, or dating with super-powered team ups. Honestly, most people who spend a lot of time with Batman end up throwing on a vibrant costume and fighting criminals or superheroes anyway. He just has that affect on people.

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Throughout the character’s long comic, film and TV history, Batman has long turned to the female villains populating Gotham City to fill the void of romance in his bat-shaped heart. The seductive, cunning, and equally love-sick ladies of this list inhabit many qualities and powers that attract Gotham’s Most Eligible Vigilante in different ways. Although most of his relationships have ended in tragedy, Batman’s romances with the following women have greatly impacted his life, as they represent how both the hero and the villainess long for some semblance of a meaningful, normal love life.

15. DID: CATWOMAN

Catwoman New 52

Catwoman is one of the Caped Crusader’s longest enduring, on again off again, will they or won’t they romances. In pretty much every incarnation, whether it be film, TV or comics, Bruce Wayne and Selina Kyle have made it happen. Catwoman’s mainstream comic debut occurred in June, 1940 in Batman #1. Since then, Selina Kyle has arguably become Batman’s greatest love over the course of their hot and heavy history, exploring different emotional and entertaining “what ifs” for the timeless characters.

For instance, Earth-Two’s classic incarnation results in their marriage and the birth of a daughter, Helena, who would go on to follow in their footsteps as the Huntress. More recently in Jeph Loeb’s Batman: Hush, Bruce actually revealed his secret identity to Selina as they carried on a steamy but doomed love affair. Catwoman has also clawed her way into both Tim Burton’s and Christopher Nolan’s films and there is no doubt that their relationship will pop up again in a future flick.

14. DID: TALIA AL GHUL

The other great love of Batman/Bruce Wayne’s life. First appearing in Detective Comics #411,  Talia al Ghul has also been portrayed in most Batman media as a major love interest. As the deadly and cunning heir to Ra’s al Ghul and the League of Assassins, Talia’s feelings toward Bruce have wavered depending on the continuity but predominantly the two share a very strong, if strained, connection. Throughout, Talia has struggled with remaining loyal to her father’s mission or embracing Batman’s moral crusade against crime in Gotham. In 1987’s Son of the Demon arc, the two sleep together and had a son, Damian Wayne, and after being kept secret from Bruce for a number of years, Damian becomes the fifth Robin in 2009’s Batman Reborn arc of Grant Morrison’s Batman and Robin series.

In 2012’s The Dark Knight Rises, Marion Cotillard plays Miranda Tate who in a twist (or not) is actually revealed to be Talia al Ghul vengefully returning to Gotham to finish her late father’s mission from the first film of the trilogy. The character has more recently (and traditionally) been played by Morena Baccarin for the DC Animated Original Movies Son of Batman and Batman: Bad Blood.

13. DID: POISON IVY

Poison Ivy with Batman

The cunning, seductive, poisonous pheromone-secreting Pamela Isley uses her powers to control the men who stand in her way, including Batman, and their attraction is more driven by the one-sided, uncontrollable lust she affects in her victims rather than true romantic feelings. Still, Poison Ivy has been seducing Batman since 1966’s Batman #181 and most of their stories follow the pattern set up by the inaugural issue. Tim Sale created a visually intriguing and fairly horrifying version of Ivy’s seduction methods for the pages of The Long Halloween.

Poison Ivy does have a life outside of Batman and her hobbies include fighting for justice on behalf of nature, as she more recently attempted in Detective Comics #23.1 while attempting to return Gotham to its greener, less man-made roots by force. She also teamed up with the likes of Catwoman and Harley Quinn in Paul Dini’s Gotham City Sirens series that’s also being adapted into a feature film, directed by David Ayer with Margot Robbie reprising her Harley Quinn role and producing.

12. DID: NOCTURNA

nocturna and batman

Nocturna, or Natalia Knight, made her debut in the pages of Detective Comics in 1983 where she proceeded to appear out of nowhere, cause trouble, and vanish without a trace more than a few times. She also boasted some powers of romantic persuasion in the form of a perfume which rendered her irresistible, much like how regular perfume ads portray cosmetics. On top of that, an accident while working at the Gotham City Observatory bleached her skin completely white. Forever after, she suffered from an intense sensitivity to light. Natalia ran into the Batman after joining her brother Anton in a life of crime and Bruce “I am the Night” Wayne was immediately attracted to her.

Nocturna returned in Detective Comics #543 and successfully battled Bruce for custody of Jason Todd as part of as scheme to force him to marry her. Nocturna had also learned that Bruce was Batman and agreed to not kiss and tell if he consented to their union. Now, that’s a romantic proposal!

11. DID: JILLIAN MAXWELL

Jillian Maxwell marrying Batman

Thanks to the untimely symptoms of Scarecrow’s fear toxin, Bruce Wayne fell pretty hard for Jillian Maxwell in the pages of Jeph Loeb and Tim Sale’s first team-up, Batman: Legends of the Dark Knight Halloween Special #1. Unfortunately for Bruce, Jillian was only really gunning for the billionaire playboy’s immense fortune. Fortunately for Bruce, good ol’ Alfred had discovered Miss Maxwell’s violent penchant for marrying, murdering, and making off with her rich victims’ fat stacks of cash and he cut the cord quickly. Even when Bruce tries to fall for the good ones, the good ones turn out to be evil. At least Jillian was only a normal, greedy con artist and not a powerful and deadly supervillain, which is certainly progress in Mr. Wayne’s book.

10. DID: JEZEBEL JET

Jezebel Jet Batman

Jezebel Jet’s relationship with Bruce Wayne is…complicated. Creator Grant Morrison gave Jezebel a pretty tragic past for the Batman: R.I.P. arc wherein she was sold by the Black Glove criminal organization to the leader of an African country, who in turn sentenced her actual mother to death. When the leader died, Jezebel became the country’s ruler and later met Bruce at a fundraiser. Their affair was plagued by paparazzi and after an assassination attempt, she realized that Bruce is indeed Batman. That’s not the complicated part. The complicated part is that during a battle royale involving the Joker at Arkham Asylum, Jezebel revealed her secret identity as an agent for the Black Glove. Batman in turn also revealed that he was only pretending to love her as well. 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.

9. DID: THE PHANTASM/ANDREA BEAUMONT

Andrea Beaumont DCAU

Andrea Beaumont, who only plays a prominent role in Bruce’s love life in the critically acclaimed animated film Batman: Mask of the Phantasm, is another heartbreaking entry in the romantic annals of the Dark Knight. In the film, Andrea and Bruce fall in love while in college and even get engaged, but she was forced to leave the country after her father double-crossed the Gotham mafia. Years later, Andrea mysteriously reappeared in Gotham and Bruce’s life. The romantic reunion was short-lived, however. After her father was tracked down and murdered by the mob, she poured all her time and resources into training herself for revenge. Similar to how Bruce took up the mantle of Batman, Andrea became the Phantasm and began tracking down and eliminating her father’s killers. Batman sure can pick ’em!

8. DID: TEN OF THE ROYAL FLUSH GANG

Melanie Walker Royal Flush Gang Ten

Others who have taken up the Batman cowl haven’t been spared the heartbreak that goes along with it. Terry McGinnis, the Caped Crusader of the DCAU’s Batman Beyond, fell suddenly for Melanie Walker after a fight with his longtime girlfriend. After sharing an unexpected kiss, Terry and Melanie agreed to meet up again for a date. However, a happy ending just wasn’t in the cards.

Terry, currently the sole crime-fighting member of that future’s Bat Family, unknowingly clashed with Melanie who was also putting some hours in with her own family business as Ten of the Royal Flush Gang. Terry would eventually learn of her secret identity, and although he put a stop to their relationship before it could really get started, Batman’s influence would ultimately help Melanie reform and leave her life of crime for good.

7. DID: PENUMBRA

Penumbra vs Batman and Catwoman

The New 52’s Detective Comics #0 introduced this particularly deadly assassin while Bruce Wayne was still training to become Batman. Bruce originally began falling 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. The identity of that assassin? Well, it was of course Mio!

Mio, now known as Penumbra, after being trained by none other than Ra’s al Ghul himself, travels to Gotham  on another mission and is confronted by Batman. The Dark Knight manages to discover her identity after finding a way around her nifty and very League of Assassins-copyrighted shadow-bending powers. Although he tries to reason with the Mio whom the young Bruce once knew and loved, she escapes. What does Penumbra get out of this relationship? Locked in a cell maybe forever by Ra’s al Ghul, who is very much disappointed in her abilities as an assassin.

6. DID: LINA MULLER (THANATOS/SOPHIA SANTOS)

Lina Muller Sophia Santos Thanatos

Sophia Santos is a busy lady. First, she’s the costumed leader of the Death’s-Head terrorist group who in Batman #305 masterminds a string of attempted bombings in Gotham City. Also, Sophia blocks out time to pose as reporter “Lina Muller” in order to seduce and lure millionaires to Gotham Isle, sap them of any common sense with a device called the “Fortu-Tron,” and laugh as they gamble away the entirety of their trust fund.

At least, this is what she subjects Bruce to. Sure, Bruce loses some dough because of Sophia’s beauty and wiles, and to a device that Amos Fortune (its inventor) should have just mass produced and sold to every casino in the world, but Batman comes away a winner in the end by outsmarting and defeating Sophia and Death’s-Head.

5. QUEEN BEE

Marcia Monroe spanked by Batman

Batman’s ex-girlfriends seem to just keep popping back up in his life as criminals no matter what the Dark Knight does. Enter Queen Bee, a.k.a. wildcard thrill seeker Marcia Monroe who makes both a spectacular debut and abrupt finale in the Batman comic of the swinging ’60s, Brave and the Bold #64. Their meeting was a most romantic and intimate affair wherein Batman saved her from falling off of a bridge (because that’s her idea of fun) and then proceeds to spank her like a naughty child in the middle of the street in full view of the public. So, justice served. Marcia’s next bold and completely normal move for an attractive woman written into the plotline of a 1960s comic book is to profess her love for Batman.

Batman promises to reveal his secret identity once they’re married, but unfortunately, Marcia disappears. She eventually returns to Gotham as the Queen Bee and member of the crime syndicate known as CYCLOPS, in order to double-cross Batman and hoodwink some people out of precious, precious gems, only to vanish once more. Queen Bee is definitely due for a reboot!

4. THE JOKER

Martha Wayne Flashpoint Joker

In the Flashpoint timeline and related stories, Joe Chill murdered Bruce Wayne — not Bruce’s parents. This results in his father, Thomas Wayne, becoming that timeline’s far more brutal and tortured Batman. What happens to his wife, Martha? Well, she tracks down Joe Chill, beats him to death with a hammer, and becomes Flashpoint‘s Joker, complete with a Glasgow smile sliced into her cheeks.

Her gruesome accomplishments as the Joker include kidnapping Harvey Dent’s daughter and tricking Jim Gordon into shooting her, murdering Gordon, and jumping to her death when Thomas reveals that there’s a way to rewrite the timeline so that Bruce lives and becomes Batman. Maybe Thomas and Martha should have tried their hand at marriage counseling?

3. SHOULD: WHITE RABBIT

White Rabbit

A newer addition to the Batman canon, Jaina Hudson took Bruce down the rabbit hole in her first appearance in 2011’s Batman: The Dark Knight #1. Jaina’s unique powers allow her to completely split herself into two separate bodies and personalities. This, combined with the fact that the character has only very recently been introduced, means there’s plenty of potential for a budding romance with the Dark Knight.

Jaina’s naturally another one of Gotham’s wealthy socialites and she and Bruce immediately begin flirting within seconds of laying eyes on one another. At this point, Bruce’s future criminal ex-girlfriend bat-radar should be blaring, but when it comes to women, he always gives them the benefit of the doubt in terms of supervillainy. Batman becomes acquainted with Jaina’s White Rabbit persona when he attempts to stop a mass breakout of Arkham, and is forced to go toe to toe with several baddies pumped up by a mysterious super steroid courtesy of Miss Hudson. White Rabbit makes it a point to also come onto Batman before her escape, so all secret identities/alter ego bases are covered. Mr. Wayne definitely has a type!

2. SHOULD: LADY SHIVA

Lady Shiva

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 master in seemingly more martial arts styles than Batman himself. In 1988’s Batman#427, part of the infamous Death in the Family arc, then Robin Jason Todd and Batman confront Lady Shiva about whether or not she could be Todd’s biological mother. For Batman, this would be a pretty good “in” with Lady Shiva but it’s revealed that she is not and proceeds to all but defeat Batman in combat (Robin intervened at the last second).

As time went on, Lady Shiva slowly became more involved with the goings-on of Gotham City and the Bat Family, even training the third Robin, Tim Drake. For one of the deadliest killers in DC Comics, she certainly has a gentler, more maternal side (at least for Robins). But that’s just another check in the “romance” column for Batman. Do they both love beating the crap out of people using insane martial arts skills? Yes. Do they both love Robins? Yes. Batman and Lady Shiva should be a match made in DC heaven.

1. SHOULD: HARLEY QUINN

Harley Quinn kissing Batman

Dr. Harleen Quinzel first appeared not in the comics, but as an original character and girlfriend of the Joker in the acclaimed Batman: The Animated Series episode, “Joker’s Favor.” Her love affair with Joker is predictably unpredictable and mostly unhealthy for Harley and most of Gotham City in general. So, their mutual friend Batman could one day be her perfect rebound! It’s a long shot, yes, but there is some precedent for their potential hook up.

In the Batman: The Animated Series episode Harley’s Holiday, Harley somehow receives a clean bill of health and is released from Arkham. Although her attempt to live an honest life only results in theft, kidnapping and a battle with the army, Batman sympathizes with her efforts and manages to save her life, earning an unexpected kiss from Harley Quinn. Also, in the one-shot Harley Quinn Valentine’s Day Special #1, Harley fantasizes about falling in love with Bruce Wayne and her scheming wins a date with him at a bachelor charity auction. Her misadventures lead to Harley nabbing a kiss from both Bruce Wayne and Batman, although she fails to notice any smooching-related resemblances. Who knows? Harley might change her tune one day and end up in Batman’s loving arms! Or, Batman can completely lose his mind. Either way would probably work for Harley Quinn! Maybe in the upcoming Batman and Harley Quinn animated film?

Which supervillain hookup with Batman was your favorite? Which ones are you hoping to see in the future? Let us know in the comments!

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