Many superheroes have a muse, partner, or spouse that they care for more than their own well-being. Superman has Lois Lane, Spider-Man has Mary Jane, and The Flash has Iris West. Batman, however, has had multiple love interests while on his pursuit of justice.
Between fighting crime as Batman while balancing the playboy alter ego of Bruce Wayne, the Caped Crusader rarely has time for a steady relationship. From journalists to notorious assassins, Batman has had a variety of different flings that most superheroes cannot claim to have had. Some are a match made in heaven, others are a match made in Arkham Asylum.
10 Talia Al Ghul
It's really hard to find a relationship in Batman's life more toxic than this one. Talia al Ghul, daughter of the League of Assassins' leader Ra's al Ghul, seems like the perfect match. She's stunningly beautiful and a clever assassin suitable for Bruce Wayne's combat driven hobby. But Talia is pure unadulterated evil which makes her the worst possible match.
Talia drugs Bruce Wayne to get herself pregnant and have his son, Damian Wayne. Batman then has to train his estranged son to break him out of the old habits he learned from Talia. None of the other women in Batman's life can say they impregnated themselves without his consent and gave birth to a bratty monster unleashed into the world. Talia brought the worst kind of family drama possible in Batman's life giving her the top spot as Bruce's worst match.
9 Jezebel Jet
Supermodel Jezebel Jet seems like the perfect like the perfect match for Bruce when they first met at a fundraiser for Africa. Bruce starts dating Jezebel Jet around the same time Talia revealed that Bruce has a son. But much like Talia, Jezebel uses Bruce's love to betray him. After figuring out that Bruce is batman, he attempts to save her when she's kidnapped by the Black Glove, only to have her reveal that she has been a part of the Black Glove all along. Jezebel and Talia, who have a strong hostility towards each other, are better suited for each other than Bruce.
8 Batgirl/Barbara Gordon
Batgirl/ Barbara Gordon, daughter of Gotham PD's Commissioner Jim Gordon, decided to follow in the Caped Crusader's footsteps and use her genetically gifted detective skills as Batgirl. Many storylines have Barbara and Dick Grayson as an on-again, off-again relationship. However, in the Batman Beyond 2.0 series, Bruce and Barbara have a fling that leaves her pregnant, causing conflict between Dick and Bruce (Barbara later miscarries). Between Bruce's long history with Commissioner Gordon and deep personal ties with Dick as the first robin, this is considered by many fans a very problematic relationship and a close runner up for the worst possible match.
7 Pamela Isley/Poison Ivy
Poison Ivy never tricked Bruce to impregnate herself like Talia al Ghul and she's not the daughter of his best friend like Barbara Gordon, so she's not the worst possible match in Bruce's life. But she does have the dangerous ability to make any unsuspecting target completely love sick over her. While Pamela has a noble quest in protecting the environment and defending the ecosystem, any romantic relationship she's in, whether it's Harvey Dent or Bruce Wayne, is just a means to an end to serve her ultimate botany fetish.
6 Andrea Beaumont
It's hard to call Andrea Beaumont aka The Phantasm a bad match. The that they meet at a cemetery and bonded over the loss of their parents seems as if their relationship is destined. But after her father is murdered by the mafia, Andrea decides to use her family's money and train herself to avenge her father's death as The Phantasm. In almost every way, Bruce and Andrea are the same. But Andrea's desire to kill criminals to enact vengeance draws a stark ideological line between her and Batman. This difference pits them against each other and ultimately ruins their relationship.
5 Lego Joker
One of the best examinations of any relationship with Batman can be seen in The Lego Batman Movie. Lego Batman, traumatized over the death of his parents, is afraid to love again. Lego Joker recognizes that he needs Batman in his life to justify his existence (a classic analysis on Joker/Batman for decades). Once the Joker realizes that Batman is indifferent towards him rather than hating him, the Joker is heartbroken and decides to turn himself in order to prove to Batman he's worthless without his villains.
This goes on until the end where Batman decides that he does in fact hate the Joker, a heartwarming Jerry Maguire moment for the Clown Prince of Lego Crime. While there's no physical or romantic attraction in this relationship, the bond between the two shows how much they justify each other's existence and how devastating it can feel if it's not there.
4 Vicki Vale
Vicki Vale may not don a suit chasing crazed criminals at night, but her drive as a photojournalist seeking the truth about Batman matches Bruce's drive to fight crime. Vale is considered by Aficionados of the Golden Age of Batman to be the Lois Lane to Bruce's Clark Kent, appearing for the first time in the 1940's.
Modern fans know her from being the love interest in the classic 1989 film Batman, where she and Bruce share the experience of the Joker's infatuation with them. Vale is one of the most recurring love affairs in several bat-universes, making her one of the best matches for Bruce. She's also the only relationship on this list to have her very own Prince song.
3 Rachel Dawes
Rachel Dawes is a perfect fit for Bruce in a lot of ways. Not only is she a childhood friend but she is the assistant district attorney sharing Bruce's passion for ridding Gotham's streets of lunatics. While Bruce and Rachel have an established history, Batman and Rachel begin a new fling after he saves her from villains ranging from The Scarecrow to the League of Shadows.
Rachel soon finds out the true identity of Batman, and while she loves Bruce, she cannot carry on a relationship with him as Batman. Much like the tragic death of Peter Parker's girlfriend Gwen Stacy, Rachel is killed by the Joker in a warehouse explosion despite Batman's attempts to save her and Harvey Dent. Rachel's quest for justice and ultimate self-sacrifice is compatible to Bruce's overall being.
2 Silver St. Cloud
Wealthy socialite Silver St. Cloud has arguably been the closest thing to healthy long-term relationship for Bruce Wayne. Originally appearing in the Detective Comics series, she eventually discovered Bruce's secret night life fighting crime as the Dark Knight. At first, she was unwilling to continue the relationship out of fear of seeing Bruce hurt.
Later, she had a change of heart and they became engaged to be married. Sadly, Silver is very similar to Rachel Dawes except for the glaring difference that she finally accepted Bruce's double life. Silver's understanding attitude of Bruce's second life made her one of the best matches for him.
1 Selina Kyle/Catwoman
It's not a surprise that Catwoman is considered the best match as it's the most popular and extensive relationship in Batman history. This would seem like an unlikely match considering they're on polar opposite sides of the law, but in terms of lifestyles they're simpatico. These two know what it's like to deal with the underworld of Gotham in costumed secret identities, forming a strong connection despite being constantly at odds.
Although Catwoman is a jewel thief, they have a strong attraction and formed alliances to fight common enemies. Whatever time period or medium – whether it's The Golden Age of Comics, Batman: The Animated Series, Michelle Pfeiffer in Batman Returns, or Anne Hathaway in The Dark Knight Rises – Selina Kyle and Bruce Wayne have always been the Ross/Rachel of the DC Universe, with romantic gothic overtones unique to Batman's world.