Bruce Wayne’s first love interest in the comics was Julie Madison. Her first appearance was in Detective Comics #31 (1939) as Bruce’s fiancé. Julie never learns about his second identity as Batman. She actually requests that Bruce get a serious job, which he refuses, and they break up in Detective Comics #49 (1941).
For 80 years now, Bruce has been a casual dater. He dates Linda Page in the early 1940s and later Vicki Vale who makes her first appearance in Batman #49 (1948). Vicki has had suspicions that Bruce is Batman and even learns the truth in Bruce Wayne: The Road Home (2010) and in Tim Burton’s film, Batman (1989). While Vicki has popped in and out of the comics over the years, her relationship with Bruce never lasts very long. After the social anxieties triggered by Fredric Wertham in the 1950s, DC decided to introduce Kathy Kane (Batwoman) as a love interest to reaffirm Batman’s heterosexuality. But this relationship didn’t go anywhere either.
In the 1970s, Talia al Ghul (daughter of Ra’s al Ghul) was introduced as a new love interest for Batman. In Batman: Son of the Demon (1987), Bruce’s romance with Talia leads her to become pregnant, but it wasn’t until Batman #655 (2006) that Damian Wayne is introduced as the fruit of their union. While Bruce takes Damian under his bat wing, his relationship with Talia never turns into anything serious.
Bruce cannot settle down, because he does not feel that he can balance the role of husband and protector of Gotham. In Batman #214 (1969), mobsters actually think that marriage would weaken Batman. They try to get Batman married, because they feel that his wife would not let him out every night. Bruce’s reluctance to commit to a woman shows that he, too, believes marriage would inhibit his abilities to fulfill his true calling.
The closest Bruce ever gets to marital bliss is with Selina Kyle. Their relationship has been very tumultuous over the years, though. Catwoman makes her first appearance in Batman #1 (1940) as The Cat. Batman is attracted to her and actually allows her to escape capture on more than one occasion. Bruce and Selina/Batman and Catwoman have many romantic encounters throughout the franchise, and Selina and Bruce actually do get married and have a child, Helena Wayne (who becomes Huntress), on Earth-Two in Superman Family #211 (1981). More recently, in Batman Vol. 3 #24 (2017), Bruce proposes to Selina. Their wedding was planned to occur in Batman #50 (2018), but Selina realizes that marrying Bruce would ultimately destroy Batman. She sacrifices marital happiness to preserve Gotham’s hero.
Bruce Wayne is a charmer and ladies’ man, but he is also protector and defender of Gotham City. His various relationships certainly make him seem more like a regular guy, but Bruce Wayne is anything but regular and can’t be grounded. Gotham needs the Bat, so he must remain a bachelor.