Batman had several love interests throughout the years, in both his golden age and modern day incarnations, and we've considered some already. There was the Batwomen and the Catwomen.
This doesn't even include gun-slinging sirens in debutannte Ruby Ryder and her counterpart, the sultry singer Linda Lewis. What of the non-heroic or villainous females in the lives of Bruce Wayne?
We would have to start with the trifecta of the golden and silver age, the three non-costumed lasses that captured both Wayne's hearts.
First there was Julie Madison, who was engaged to Wayne although her acting career and his crime fighting career pulled them each in opposite directions. After a couple of confrontations with Clayface, they two drifted apart. On Earth-Two, Julie changed her name to Portia Storme as she became a Hollywood star. On Earth-One, she became Princess Portia as she wed the ruler of Moldacia in Europe.
Then there was Linda Page, a rich debutante and heiress to an oil fortune, although what she truly was invested in was her engagement with Wayne. Again, Batman got in the way, and once she began her career as a nurse she too found greater fulfillment in helping others... which is what ensnared her beau in the bat-suit. What became of her on Earth-One is unknown, although on Earth-Two she eventually married shortly before that Bruce finally found his true love.
Finally, there was photojournalist Vicki Vale, whose tenacity was exceeded only by her fellow reporter from Metropolis, Lois Lane. On Earth-Two, Vicki was first employed with Picture Magazine, and covered the first appearance of the mysterious Mad Hatter. She was a repeatedly attempt to make a connection between Bruce Wayne and Batman, although she never found conclusive proof. She eventually left Picture Magazine for Vue Magazine, and nearly became the bride to the Shah of Nairomi when he proposed to her, until her fake engagement with Batman dissuaded him.
Vicki Vale of Earth-One had a similar history with her Batman and his alter ego, although she eventually married Tom Powers. Years later, she returned to Gotham City from an extended assignment with Vue Magazine in Paris, Vicki was now divorced. After getting into a brief love triangle between her, Bruce Wayne and Selina "Catwoman" Kyle, Vale abandoned thoughts of rekindling her romance with Wayne. She would become deeply involved in physical fitness pursuits instead.
And, of course, during that period Kathy "Batwoman" Kane eventually decided to settle down with another man, marrying and having kids on Earth-Two. Her Earth-One twin never found love, only the tragic end to her life at the hands of the Bronze Tiger. Something that mirrored what became of Earth-Two's Catwoman, torn from her husband and daughter in the prime of her life.
There were momentary pauses in their lives, in which the Waynes were briefly captivated by the presence of policewomen Patricia Powell and Shirley Holmes. None of these relationships developed into anything more. However, there were a couple of platinum haired ladies that added wrinkles to the dynamics of the Batman Family, in different ways... for good and for ill.
There was Silver St. Cloud, a party planner of Gotham City who immediately captured Wayne's attention as no other woman had, save perhaps for Catwoman and Talia. And she came without complications that would develop from leading a double life, as had occurred with the other ladies. However, after she began to date Bruce she met Batman, and right away made the connection between the two. Fearing for Wayne's life when he moonlighted as a superhero, Silver eventually broke off their relationship. Something that is telling, however, is when the Earth-Two Batman's daughter Huntress was visiting the Earth-One Batman, and he reflected on how he yearned to start a family with St. Cloud. Sadly, it was not to be.
And on the Huntress' world, it was while the heroine was tracking down some corrupt psychologists at Arkham Asylum that she encountered Silver's doppleganger in Lucinda Morrison. Licinda was manipulated by drugs into working for the crooks, and once she fled the scene she assumed the new identity as psychiatrist Dr. June Moorman. It was at her place of employment that she was enlisted to have a therapeutic session with the Huntress, whose alter ego of Helena Wayne was being tormented with fear she may follow in her mother's wicked ways. After a confrontation between the two, Morrison was held in custody and went to jail to pay for her criminal deeds. Morrison never met Bruce, but found torment from his heiress after his passing just as St. Cloud a universe away.
While the Earth-One Bruce Wayne had a strong longterm interest in the daughter of his immortal foe Ra's Al Ghul named Talia, nothing ever came of it given their conflicting goals. The Earth-Two Bruce Wayne never met her counterpart, Lo-Lanke, wife to the immortal Gotham gangster Chang of the Green Flame Tong.
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