It’s September, which means we’re celebrating everything Batman related, including some of his greatest treasures. However, today we’re going to spotlight an item that can’t be found in his utility belt or the Batcave trophy room—his little black book of exes. Batman is a master at martial arts and forensics, but his skills as a long-term boyfriend are lacking. While his black book might be full—and it is, Bruce Wayne is Gotham’s most eligible bachelor, after all—most of those relationships didn’t end very well. Let’s take a look at some of the more memorable ones…
Julie Madison
Meet Cute: Bruce and Julie were college sweethearts who met while working on a stage production. By the time she was introduced in 1939’s Detective Comics #31, the two were already engaged.
Sinking of the Ship: Every time Julie encouraged Bruce to get a job, he would laugh in her face. (We get that you’re rich enough that you don’t need to work a 9-to-5, but that’s still a pretty weird response, dude.) There’s also the strange time when Bruce had Julie dress up as Robin (if you think we’re joking then check out 1941’s Detective Comics #49). Julie eventually got tired of telling Bruce to make something of himself, so she called off their engagement. In World’s Finest #248, we learn that she became a royal princess, so I guess she did alright for herself.
Vicki Vale
Meet Cute: Tim Burton’s 1989 Batman film features a whirlwind romance between Michael Keaton’s Bruce Wayne and Kim Basinger‘s Vicki Vale. Bruce was fascinated by Vicki’s photography and invited her to dinner. One thing led to another and…
Sinking of the Ship: Bruce slept with Vicki on their first date and then ghosted her. Not cool, man. The couple were able to get their relationship back on track, but by the time Batman Returns rolled around, Vicki was gone because “she couldn’t handle the duality.” Maybe she just couldn’t handle his weird habit of sleeping upside down.
Linda Page
Meet Cute: Linda was an old society friend who Bruce ran into on the street in 1941’s Batman #5. He was intrigued by her decision to leave the socialite life behind and become a working girl, and they began a relationship.
Sinking of the Ship: Where to begin? There’s the time he left her stranded on a broken down Ferris wheel (1942’s Detective Comics #69), or the time when he got engaged to somebody else without telling her and blamed the whole thing on Batman (1943’s Batman #15, not Bruce’s finest moment). Either way, at a certain point Linda had enough and moved on.
Kathy Kane/Batwoman
Meet Cute: Kathy first met Batman in Detective Comics #233 after she adopted the Batwoman identity.
Sinking of the Ship: In 1962’s Batman #147, Bruce wanted to get rid of Kathy, so he made a silhouette of himself kissing another woman. He later explained that it was just his cousin, which really doesn’t make it any better. 2011’s Batman Incorporated #4
Rachel Dawes
Meet Cute: Rachel and Bruce were childhood friends who met when Rachel’s mother took a job at Wayne Manor. The two stayed in contact after Bruce’s parents died, with Rachel wisely trying to talk Bruce out of some of his dumber decisions. She eventually became an assistant district attorney.
Sinking of the Ship: The two of them never actually got together. Although they shared a kiss at the end of Batman Begins, Rachel told Bruce that they can’t be together until his work as Batman is done. Bruce tried to win her over again in The Dark Knight, but Rachel was in a committed relationship with Harvey Dent. She was later killed by the Joker, robbing Bruce of his closure.
Silver St. Cloud
Meet Cute: Silver was a high society girl who Bruce met at a yacht party in Detective Comics #470. Unlike Bruce’s other society dates, Silver was smart enough to quickly deduce that he was Batman, which made any potential relationship difficult.
Sinking of the Ship: In Batman: The Widening Gyre #6, Bruce attacked Silver and accused her of being an evil robot (?!?!?!?). Amazingly she immediately accepted his apology (!!!). After years of breaking up and getting back together, they finally got engaged, but Silver’s life was cut short when the villainous Onomatopoeia sliced her throat.
Rachel Caspian
Meet Cute: Bruce felt an immediate attraction to Rachel when Leslie Tompkins introduced them in Detective Comics #575.
Sinking of the Ship: Bruce made romantic overtures towards Rachel even after she told him she was getting ready to become a nun. She eventually gave in and the two became engaged, but it was still a bit skeevy. After her father died, Rachel ended her engagement to Bruce and became a nun in Detective Comics #578.
Talia al Ghul
Meet Cute: Batman first met the daughter of Ra’s al Ghul in Detective Comics #411
Sinking of the Ship: In DC Special Series #15, Ra’s performed a wedding ceremony between Batman and Talia. During the honeymoon, Batman knocked Talia out when she tried to consummate the marriage and left their suite to go do Batman stuff. It’s amazing they got back together after that at all. Bruce probably doesn’t tell this story to Damian.
Wyldstyle
Meet Cute: Honestly, I’ve always been curious about this. When we first see Batman and Wyldstyle in The Lego Movie, they’ve already been dating for some time. Lucy is a freedom fighter and Master Builder, and she isn’t part of the DC Universe…so how did she first hookup with Batman? Maybe they both went to the same escape room or something.
Sinking of the Ship: This one ended for two reasons. The first was because Batman wasn’t an attentive boyfriend, ditching Wyldstyle when it suited him. The second was Wyldstyle was falling for Emmett, who is voiced by Chris Pratt. Batman is quite a catch, but even the Dark Knight has a hard time competing with Pratt (even when he’s in Lego form).
Selina Kyle/Catwoman
Meet Cute: They’re still arguing on the circumstances of their first meeting, but our comics library says they first met when she tried to rob a yacht all the way back in 1940’s Batman #1. The Dark Knight was so taken by her beauty that he actually let her escape.
Sinking of the Ship: Bruce and Selina (under the guise of Elva Barr) first got engaged in 1943’s Batman #15, but the engagement was a sham to get Catwoman to give up crime. Uh…how were you expecting this to end Bruce? Were you planning on taking this charade through the honeymoon? Sadly, even though these two are clearly made for each other, things between Bruce and Selina haven’t gotten much better since then, with Selina running out on their wedding in 2018’s Batman #50Joker War. Call me crazy, but with the longest, most consistent relationship of anyone on this list, and that fact that they’re still clearly smitten with each other, I still think these two kids can work things out.
Just as long as Bruce doesn’t ask her to dress up as Robin.
Joshua Lapin-Bertone writes about TV, movies and comics for DC.com, is a regular contributor to the Couch Club and writes our monthly Batman column, “Gotham Gazette.” Follow him on Twitter at @TBUJosh.
NOTE: The views and opinions expressed in this feature are solely those of Joshua Lapin-Bertone and do not necessarily reflect those of DC or Warner Bros. Discovery, nor should they be read as confirmation or denial of future DC plans.
[[{“value”:”It’s September, which means we’re celebrating everything Batman related, including some of his greatest treasures. However, today we’re going to spotlight an item that can’t be found in his utility belt or the Batcave trophy room—his little black book of exes. Batman is a master at martial arts and forensics, but his skills as a long-term boyfriend are lacking. While his black book might be full—and it is, Bruce Wayne is Gotham’s most eligible bachelor, after all—most of those relationships didn’t end very well. Let’s take a look at some of the more memorable ones…
Julie Madison
Meet Cute: Bruce and Julie were college sweethearts who met while working on a stage production. By the time she was introduced in 1939’s Detective Comics #31, the two were already engaged.
Sinking of the Ship: Every time Julie encouraged Bruce to get a job, he would laugh in her face. (We get that you’re rich enough that you don’t need to work a 9-to-5, but that’s still a pretty weird response, dude.) There’s also the strange time when Bruce had Julie dress up as Robin (if you think we’re joking then check out 1941’s Detective Comics #49). Julie eventually got tired of telling Bruce to make something of himself, so she called off their engagement. In World’s Finest #248, we learn that she became a royal princess, so I guess she did alright for herself.
Vicki Vale
Meet Cute: Tim Burton’s 1989 Batman film features a whirlwind romance between Michael Keaton’s Bruce Wayne and Kim Basinger‘s Vicki Vale. Bruce was fascinated by Vicki’s photography and invited her to dinner. One thing led to another and…
Sinking of the Ship: Bruce slept with Vicki on their first date and then ghosted her. Not cool, man. The couple were able to get their relationship back on track, but by the time Batman Returns rolled around, Vicki was gone because “she couldn’t handle the duality.” Maybe she just couldn’t handle his weird habit of sleeping upside down.
Linda Page
Meet Cute: Linda was an old society friend who Bruce ran into on the street in 1941’s Batman #5. He was intrigued by her decision to leave the socialite life behind and become a working girl, and they began a relationship.
Sinking of the Ship: Where to begin? There’s the time he left her stranded on a broken down Ferris wheel (1942’s Detective Comics #69), or the time when he got engaged to somebody else without telling her and blamed the whole thing on Batman (1943’s Batman #15, not Bruce’s finest moment). Either way, at a certain point Linda had enough and moved on.
Kathy Kane/Batwoman
Meet Cute: Kathy first met Batman in Detective Comics #233 after she adopted the Batwoman identity.
Sinking of the Ship: In 1962’s Batman #147, Bruce wanted to get rid of Kathy, so he made a silhouette of himself kissing another woman. He later explained that it was just his cousin, which really doesn’t make it any better. 2011’s Batman Incorporated #4
Rachel Dawes
Meet Cute: Rachel and Bruce were childhood friends who met when Rachel’s mother took a job at Wayne Manor. The two stayed in contact after Bruce’s parents died, with Rachel wisely trying to talk Bruce out of some of his dumber decisions. She eventually became an assistant district attorney.
Sinking of the Ship: The two of them never actually got together. Although they shared a kiss at the end of Batman Begins, Rachel told Bruce that they can’t be together until his work as Batman is done. Bruce tried to win her over again in The Dark Knight, but Rachel was in a committed relationship with Harvey Dent. She was later killed by the Joker, robbing Bruce of his closure.
Silver St. Cloud
Meet Cute: Silver was a high society girl who Bruce met at a yacht party in Detective Comics #470. Unlike Bruce’s other society dates, Silver was smart enough to quickly deduce that he was Batman, which made any potential relationship difficult.
Sinking of the Ship: In Batman: The Widening Gyre #6, Bruce attacked Silver and accused her of being an evil robot (?!?!?!?). Amazingly she immediately accepted his apology (!!!). After years of breaking up and getting back together, they finally got engaged, but Silver’s life was cut short when the villainous Onomatopoeia sliced her throat.
Rachel Caspian
Meet Cute: Bruce felt an immediate attraction to Rachel when Leslie Tompkins introduced them in Detective Comics #575.
Sinking of the Ship: Bruce made romantic overtures towards Rachel even after she told him she was getting ready to become a nun. She eventually gave in and the two became engaged, but it was still a bit skeevy. After her father died, Rachel ended her engagement to Bruce and became a nun in Detective Comics #578.
Talia al Ghul
Meet Cute: Batman first met the daughter of Ra’s al Ghul in Detective Comics #411
Sinking of the Ship: In DC Special Series #15, Ra’s performed a wedding ceremony between Batman and Talia. During the honeymoon, Batman knocked Talia out when she tried to consummate the marriage and left their suite to go do Batman stuff. It’s amazing they got back together after that at all. Bruce probably doesn’t tell this story to Damian.
Wyldstyle
Meet Cute: Honestly, I’ve always been curious about this. When we first see Batman and Wyldstyle in The Lego Movie, they’ve already been dating for some time. Lucy is a freedom fighter and Master Builder, and she isn’t part of the DC Universe…so how did she first hookup with Batman? Maybe they both went to the same escape room or something.
Sinking of the Ship: This one ended for two reasons. The first was because Batman wasn’t an attentive boyfriend, ditching Wyldstyle when it suited him. The second was Wyldstyle was falling for Emmett, who is voiced by Chris Pratt. Batman is quite a catch, but even the Dark Knight has a hard time competing with Pratt (even when he’s in Lego form).
Selina Kyle/Catwoman
Meet Cute: They’re still arguing on the circumstances of their first meeting, but our comics library says they first met when she tried to rob a yacht all the way back in 1940’s Batman #1. The Dark Knight was so taken by her beauty that he actually let her escape.
Sinking of the Ship: Bruce and Selina (under the guise of Elva Barr) first got engaged in 1943’s Batman #15, but the engagement was a sham to get Catwoman to give up crime. Uh…how were you expecting this to end Bruce? Were you planning on taking this charade through the honeymoon? Sadly, even though these two are clearly made for each other, things between Bruce and Selina haven’t gotten much better since then, with Selina running out on their wedding in 2018’s Batman #50Joker War. Call me crazy, but with the longest, most consistent relationship of anyone on this list, and that fact that they’re still clearly smitten with each other, I still think these two kids can work things out.
Just as long as Bruce doesn’t ask her to dress up as Robin.
Joshua Lapin-Bertone writes about TV, movies and comics for DC.com, is a regular contributor to the Couch Club and writes our monthly Batman column, “Gotham Gazette.” Follow him on Twitter at @TBUJosh.
NOTE: The views and opinions expressed in this feature are solely those of Joshua Lapin-Bertone and do not necessarily reflect those of DC or Warner Bros. Discovery, nor should they be read as confirmation or denial of future DC plans.”}]]
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