Bruce Wayne / Batman

Earth-Two
1.  Julie Madison  - From 1939 to 1941 (Detective Comics #31-49), Bruce was depicted as being engaged to movie star Julie Madison, who was oblivious to his life as Batman. The two eventually broke up. (Julie was introduced in Detective Comics #31, and their break-up was shown in issue #49)

2.  Selina Kyle / Catwoman  - Batman first met Catwoman. Immediately attracted to the thief, in their first encounter, he lets her go. (Batman #1, 1940) They would have a continual romantic tension over the years, amidst his other love interests and girlfriends.

2.  Linda Page  - Bruce Wayne’s next girlfriend lasted from 1941 to 1943 (Batman #5-15), the two breaking up without her ever learning his true identity.

There is no clear dividing line between where the adventures of Earth-Two Batman ended and those of Earth-One Batman began, but many have claimed it should be considered the introduction of the yellow oval on Batman’s emblem in 1964. All I know is that the character of Vicki Vale was treated later on as an Earth-One character. Batwoman, introduced later, is confirmed to exist on Earth-Two, but it is also stated that Batman never returned this version of the characters' affections, so she doesn't really count as a love interest.

It was later revealed that Earth-Two Batman eventually turned Catwoman into an honest woman, married her, and had a child, before being killed on the job. His daughter, Helena Wayne, grew up to become the superheroine Huntress

Earth-One / Post-Crisis / New Earth
1.  Dawn Golden  was Bruce’s childhood friend, the daughter of another billionaire. The two later dated in college, and she broke his heart. (Batman: The Dark Knight #1-5, 2011)

2.  Selina Kyle / Catwoman  - The criminal and the hero would have the same romantic tension follow them throughout their careers. They would go on a few dates during this time. (Long Halloween, The Batman Files).

3.  Lorna Shore  was a museum curator that Bruce fell hard for. The two started dating, with Bruce stating it was the first time he felt at peace since his parent’s death. But after his (first?) encounter with the Joker (at the end of his first year as Batman), he realized there would be more villains like this and, that his life was too dangerous for love, breaking up with Lorna. She then moved to Metropolis. (Batman: Confidential #8, Oct. 2007)

4.  Viveca Beausoleil  (The Batman Chronicles #19)

5. Julie Madison This version of Julie was a wealthy heiress who started a relationship with Bruce. After her father was killed as a result of Batman’s actions she leaves for Africa to join the Peace Corps.(Batman and the Monster Men, 2006, Batman and the Mad Monk, 2006-2007, Batman #682, 2009, The Batman Files)

Bruce went on one date with Theodora Hackley. (Legends of the Dark Knight #2, Dec. 1989)

6.  Rachel Caspian  and Bruce fell in love. The two became engaged, and Bruce planned to give up his life as Batman to marry her. but when she realized her father had been a vicious supervillain called The Reaper, she decided to become a nun to atone for his sins.

7. Linda Page (The Batman Files)

8.  Summer Skye Simmonds  (Journey into Knight)

Also “early in his career,” Bruce fell for a woman named Jillian Maxwell after meeting her a costume party. He later discovered she was a con-artist who specialized in seducing wealthy young men and arranged their deaths so she could claim their wealth (The Batman Files, LOTDK Halloween Special #1)

In a retcon showing the first teamup between Superman, Batman, and Wonder Woman, Batman, thinking Wonder Woman dead and suddenly seeing her alive, grabs her and kisses her, resulting in her hitting him. This forshadows a future attraction between the characters (Superman, Batman, Wonder Woman: Trinity)

9. Dr. Lynn Eagles (LOTDK #65-#68)

10.  Vicki Vale , introduced in 1948, next became the character’s main love interest. She was essentially an attempt to reproduce the same dynamic of Superman and Lois Lane. She was a reporter who constantly suspected Batman and Bruce Wayne to be the same person, yet failing to prove it. She remained a presence in his life, but the two never entered into a relationship in that time.

11.  Kathy Kane / Batwoman  was introduced in 1956 (Detective Comics #233). She fought crime with Batman, with the two not knowing each other’s secret identities. Grant Morrison later retroactively showed a sexual relationship between the two. I’m not sure if this means they discovered each other’s identities. (Batman Incorporated #4, Batman #682, The Batman Files)

Batwoman and Vicki Vale were both a part of Batman’s life for several years, along with the ever-present Catwoman. In 1964, with new management at DC, the characters of Vicki Vale and Batwoman both disappeared from the comics.

In 1968's The Brave and the Bold #78, Wonder Woman plants a kiss on Batman as a trick to lure out a villain, but soon realizes that she loves him for real. Batgirl also shows a love for Bruce, but he apparently doesn't reciprocate it for Batgirl, although according to one source, he may have shown some attraction to Wonder Woman.

12.  Dinah Laurel Lance / Black Canary  shared a moment with Batman in which the two fell into a silent kiss. (Justice League of America #84, 1970, also referenced in The Batman Files)

Bruce dates Selina for the whole rest of the year, is supposedly very serious about the relationship—though in one issue he rejected her advances to focus on his crimefighting (Batman #600). Selina mentions wanting to marry Bruce, so it seems she was quite serious. (The Long Halloween, Dark Victory #5)

He also went on a date with supermodel Brittany St. James (Robin Annual #4, Jun. 1995)

Selina and Bruce may have broken up, but Batman and Catwoman still have a ton of sexual tension whenever they meet each other.) (Batman #683, Batman Incorporated #1, The Batman Files) (The Batman Chronicles #9)

13. April Clarkson (Gotham after Midnight, 2008)

14.  Kelli  (JLA 80-Page Giant #2)

Batman and Batwoman get engaged, but Batwoman breaks up Batman early in the year. (Batman Inc. #4)

Unnamed girl (Bruce breaks her heart.) (Batman: Ego, Aug. 2000)

15.  Talia Al Ghul  The daughter of terrorist Ra’s Al Ghul, who considered Batman a worthy heir, and wanted him to marry her. Although Batman had no interest in running a terrorist organization, he and Talia developed feelings for each other, which, like Catwoman, were blocked by their being on opposite sides of the law. (Detective Comics #411, May 1971)

Also like Catwoman, she would continue to experience constant tension with him through the years, amidst all his other love interests and girlfriends.(notable kiss in Batman #244, 1972)

Batwoman briefly returned to action before being killed by the League of Assassins in 1979 (Detective Comics #485, Sept. 1979)

16.  Silver St. Cloud  was a wealthy socialite introduced for a large storyline (Detective Comics #469-479, 1978-79), where she and Bruce fall for each other and form a relationship. When she discovers his identity as Batman, she breaks it off, unwilling to be with someone in such a dangerous lifestyle. (LOTDK #132-#136)

After a team-up mission, Bruce asks Wonder Woman to dinner, to which she responds "We'll see." (The Brave and the Bold #158, 1980)

Batman and Black Canary once again team up, this time with Black Canary throwing herself at him and kissing him. She is definitely the aggressor, though, with no real affection being shown by Bruce. (The Brave and the Bold #166,1980)

Batman is “wedded to” Talia and they conceive a child. (Batman: Son of the Demon)

At some point around this time, Bruce entered into a relationship with Selina Kyle, who he knew to be formerly Catwoman, now reformed. She, however, did not know him to be Batman. Appararently they actually dated for some time before breaking up.

17.  Julia Pennyworth  - Alfred’s daughter became a love interest for Bruce (Detective Comics #501, Apr. 1981).

Vicki also returned to Batman’s life (1982). Vicki and and Julia had a rivalry for Bruce’s affections. (a la Lois-Lane/Lana-Lang)

Selina Kyle saw Bruce and Vicki together, and in an act of jealousy, tried to run them off the road. Bruce went to her place as Batman, and the two engaged in a fight before she came to her senses and regretted all her actions. She is here depicted as knowing Batman's identity as Bruce, even though she never did before! This introduces a whole continuity mess into these proceedings. (Batman #355, 1982).

18.  Natalia Knight / Nocturna  - She was a thief with a disease causing albino skin and great sensitivity to light. She adopted Jason Todd, and later realized Bruce Wayne and Batman were one and the same. (1983).

The two entered into a relationship, but Bruce later realized his feelings for her were caused by a narcotic perfume she used that caused loving feelings in men. But after this, he still held serious romantic feelings for her. (The Batman Files).

Bruce’s relationship with Natalia coincided with the time that Julia, Vicki, and Catwoman were vying for his affections. And that’s not even bringing in the occasional Talia! Batman and Natalia had their last kiss in 1985. (Detective #556). The next issue he tells Catwoman his true feelings are for her. (Detective Comics #569-#570)

Bruce goes on a date with Vicki Vale. (Batman #402-#403, 1986-87)

It was revealed at that same time that Catwoman does not, at this time, know Batman's secret identity. The writers then penned a letter in a later issue admitting their mistake in #355. That issue became essentially apocryphal.

Apparently Selina and him once again formed a relationship (in which guises, I don't know) before breaking up again. Then a 1986 issue shows Catwoman attempting to woo Batman back, calling him Bruce. So once again, she knows! Even though he's never shown telling her, we can at least assume he has. (Also of note, her identity as Catwoman is publicly known, as she has been arrested before)

Vicki disappeared again around 1986, and following the Crisis, Julia was apparently wiped from continuity (Though, given how much Infinite Crisis and the aftermath liked to reinstate such continuity, she may be canon once again). So all three of those were gone by the late 80s.

Joker puts Catwoman in a brainwashing machine and essentially turns her evil again. He tries to elicit Batman's secret identity from her, but a doctor warns him to try and elicit information so soon after taking her out of the machine could cause information in her brain to be lost forever. She gives him a name, but it's the wrong one. Hence, there is an in-continuity explanation as to why Catwoman is bad again, and why she doesn't know Batman's secret identity anymore.(This story has some elements that don't apparently jive with either pre-crisis or post-Crisis continuity, and was later stated in Crisis on Infinite Earths: The Compendium, to take place on Earth-85.) (Detective Comics #570, Jan. 1987),

Batman’s relationship with Talia definitely became full-on sexual in 1987’s Batman: Son of the Demon. A child is shown at the end, believed to be the product of this union. However, it is later stated that the child was conceived after Talia drugged and raped Batman in a separate encounter.

Vicki came back again for her third stint as Bruce’s squeeze around 1989 (to coincide with her presence in the movie) until 1991. After some time in a relationship, Bruce ultimately struggles with whether or not to tell her his identity, ultimately deciding to end things again.

19.  Sharon Scott  (Bruce goes on one date with Sharon, a recurring character in Blue Devil) (Invasion tie-in)

20. Cristina Llanos (Bruce has a very short fling with Cristina.) (Batman in Barcelona)

21.  Lois Lane ? (It’s implied in “Hush”—specifically Batman #611—that Bruce has a relationship with Lois at some point. This could go pretty much anywhere. Placement is speculative, but after “Dark Knight Over Metropolis.”)

Vicki Vale again (Gotham Gazette Batman Alive? #1, Batman #475, Detective Comics #642, Batman #746)

22.  Shondra Kinsolving  was a psychic who was brought in to help Bruce/Batman recuperate after Bane broke his back in 1992. They had a brief love affair before she was kidnapped by the villain, and her half-brother, Benedict Asp, who used her powers for his own purposes, an act which regressed her mind to childhood, in 1994.

During that time, there's also some new continuity established. We see in 1993's Batman #499 that Selina Kyle's identity is now secret, even from Bruce, and she and Bruce Wayne have only met once before out of costume, and certainly never dated. This is apparently an intentional change in continuity made possible by the Crisis. In addition to wiping Julia Pennyworth out of existence, they also eliminated much of his history with Catwoman. So, during that time in the early '80s, now he had only Vicki and Natalia to contend with. Good for him! Here's another summary for that whole mess of whether Catwoman knows his identity or not....

http://thebatmanuniverse.net/catwoman-29/

23.  Vesper Fairchild  was a radio talk show host who, in 1997, began a relationship with Bruce Wayne. (Batman #540-#541, The Spectre Vol. 3 #51, Batman #544-#546, Batman #600) Bruce spends a sad night with Talia, who takes care of him.) (No Man’s Land #0)

-Vesper Fairchild (It is implied in multiple issues that Bruce is that he’s still dating Vesper this year.

24. Yuko Yagi (Batman: Chilld of Dreams)

25.  Sasha Bordeaux  was introduced in Dec. 2000, as Bruce’s bodyguard. She herself deduced his identity as Batman. He decides to train her as a fellow vigilante, and during this time, she falls in love with him, though it is at first one-sided.

Bruce won’t reveal his positive feelings to her until the end of “Bruce Wayne: Murderer?”.) (Detective Comics #775)

Yes, Bruce is still dating Vesper, until he breaks up with her in the coldest possible way—by inviting her over while hanging out with a bunch of girls with whom he’s playing Marco Polo in the pool. This is also another hint that, while we may not see it, Bruce is very much keeping his playboy persona alive with more casual side relationships.) (Detective Comics #764)

Vesper later returned and she and Bruce rekindled their relationship, before, in 2002, she was shot and killed on the orders of Lex Luthor. Bruce and Sasha were framed for the crime, but later exonerated.

Sasha was apparently killed in prison, but was actually recruited by Checkmate. Bruce eventually finds her, and confesses his love for her, but she tells him to let her go.

In 2001, Bruce dated Mallory Moxon for a time.

From Dec. 2002 to 2003, the Hush storyline featured Batman and Catwoman’s relationship finally becoming a relationship. He had known her true identity for a long time, but in these issues, the two become an item and he reveals his identity to her. After he is betrayed by a friend, the trust he showed her is replaced by his old, and now growing, paranoia, including suspicion of her, which ends the relationship. They still date and occasionally have sex after the breakup. (Catwoman Vol. 3 #32)

26.  Diana / Wonder Woman  - Apparently this tension became a thing for about ten issues, from JLA #80-90 in 2003-04 (actually kissed in #74), where they admitted feelings for each other, kissed, and talked about forming a relationship before deciding it wouldn’t lead anywhere good. (“The Obsidian Age”) (JLA #90-10

In 2005 (in Batman: Dark Detective), Silver St. Cloud came back into Bruce’s life, now engaged to a campaigning senator. The two grow close again, and she prepares to leave her fiance for him. After the senator is maimed by the joker, Bruce encourages her to stay with him until his campaign is over, which infuriates Silver into leaving him again.

In Mar. 2006 (Birds of Prey #90), Batman assists the Birds of Prey, after which Dinah plants a kiss on (a very surprised) Batman for the third time (and the second time uninvited). Dang, sorry Ollie!

Very close to that time, during the events of Infinite Crisis in mid-2006, Batman fights side by side with Sasha Bordeaux again, resulting in a passionate kiss. Batman’s caption reads something like “I tell myself I’ll never let her go again.” But apparently he did, because they never got together after that.(The OMAC Project #1-#3)

27. Amina Franklin (“Grotesk”)

Bruce still occasionally has sex with Catwoman.) (Catwoman Vol. 3 #39, Mar. 2005)

Batman discovered that he had a son with Talia (Sept. 2006). I feel like it was around this time that Talia had begun to be written as far more villainous, and this issue states that Talia even drugged and raped Bruce to conceive Damian. So the real reason I mention this is that it seemed to end any real romantic tension or possibility for Bruce and Talia. But it was later retconned again that this was not how Damian was conceived.

In late 2006/early 2007, Bruce met Jezebel Jet, another wealthy socialite, and entered into a relationship. It was later learned that she was an agent of the Black Hand, plotting to kill him. She was then killed, in 2008, on Talia’s orders. (Batman #655-#658)

28.  Karrie Bishop  (Bruce dates Karrie.) (Detective Comics #822)

29. Lilith Rutledge (LOTDK #207-#211 aka “Darker than Death”)

30. Zatanna Zatarra - Apparently during his relationship with Jezebel (??), it’s revealed that Bruce and Zatanna were childhood friends. These issues deal with Bruce finally forgiving Zatanna for the memory-wipe she commited upon him in Identity Crisis. Once he does, however, the two begin to fall for each other. They decide not to pursue it, with Zatanna stating “I can’t be with a man who is more passionate about his demons than he is about me.” (Detective Comics #833-834, 2007),

31. Kay Scott (Detective Comics #835-#836)

32. Bekka - Starting that same month (Aug. 2007, until Jan. 2008, in Superman/Batman #37-42), Batman apparently almost got his adultery on, having a period of romantic tension with Orion’s wife until she was killed. (Superman/Batman #37-#42)

Jezebel, Zatanna, and a married woman. Not a bad month!

There are hints of Bruce still living that playboy lifestyle off-panel. (Batman #655-#658), but his relationship with Jezebel continues (“Batman RIP”)

From 2009, to 2010 (in Batman: The Widening Gyre), Silver St. Cloud once again entered into a relationship with Bruce. Catwoman becomes jealous and throws herself at Bruce, with the two entering into a kiss. But he goes back to Silver.

However, the villain Onomonapeia attacks her and cuts her throat. This would seem to indicate her death, but the cliffhanger was never followed up on so we literally still don't know what happened!

In 2010 (Bruce Wayne: The Return Home), Vicki Vale finally learns Batman’s true identity, yet does not renew their relationship.

In 2011 (if that’s when Batman: The Dark Knight #1-5 takes place, it honestly could be a period-piece; I’m not sure) Batman re-encounters Dawn Golden, who is on the run from her father, who wants to sacrifice her to turn himself into an immortal. Batman fails to save her, as she is killed by her father, but Batman and Etrigan then succeed in destroying him.

Apparently, the storyline "Gotham's Most Wanted" from Batman Inc. in February 2013 applies to both New Earth and New 52 (Prime Earth) continuity (???). In that story, Talia has her and Bruce's son, Damian, killed. This, then, seemed to truly put an end to any Bruce/Talia romance. But (at least in the New 52) Damian was resurrected, and Talia's actions (here and in recent history) are blamed on the negative effects on her mind of the Lazarus Pit.

33. Una Nemo (Batman and Robin #18)

34. Annie (A time-displaced Bruce technically dates her in the year 1640, but whatever.) (Return of Bruce Wayne #2)

35.  Marsha Lamarr  (Again, a time-displaced Bruce technically dates her in 1971, but whatever.) (Return of Bruce Wayne #6)

Selina Kyle (Bruce still has sexual and romantic encounters with Selina.) (“House of Hush”, Batman Inc, Batman 80 Page Giant 2011 #1) Dawn Golden (The Dark Knight #1-5) Bruce, heartbroken by Talia’s evil ways, kisses her while Gotham burns.) (Batman Inc #11-#13)  

New 52
In 2013, Bruce met Mio/Penumbra once again in combat with Batman as she attempted an assassination, being defeated and disappearing.
 * 1)  Mio  was an agent of the League of Assassins while a pre-Batman Bruce trained wtih them. The two fell for each other. Obviously, Bruce eventually found himself in conflict with the League’s philosophies, and attempted to stop Mio from committing an assassination. The fight apparently ended with Mio being speared by fallen glass and thought dead by Bruce. She was, in truth, faking her death, and was granted superhuman control over shadows by Ra’s, taking the name Penumbra.
 * 2)  Talia Al Ghul  - From what I'm hearing, Bruce and Talia shared the same romantic bond in the New 52 Universe, where Damian was also born, before his mother had him killed. This behavior was later linked to the effect of the Lazarus Pit on her psyche, and Damian was later resurrected.
 * 3)  Selina Kyle / Catwoman  and Bruce have the same tension as in other versions.
 * 4)  Charlotte Rivers , a news reporter, had a brief relationship with Bruce Wayne before moving to Paris.  (Detective Comics #2)
 * 5)  Natalya Trusevich , introduced in 2012, was a Ukrainian concert pianist who entered into a relationship with Bruce. He even revealed his secret identity to her. But her knowledge of Batman’s identity was apparently learned by the Mad Hatter, who kidnapped her and attempted to torture her into revealing Batman’s identity. When she would not give it up, he threw her out of a helicopter.

Bruce eventually made an honest woman out of Selina, and the two became engaged. The wedding, however, was called off.

There is also apparently a woman named Jessica Cruz who recently planted a kiss on Batman (or may not have, I'm confused by what people are saying about it.

All-Star

 * 1)  Vicki Vale  - In the All-Star Universe, Vicki Vale is an apparent love interest of Bruce.
 * 2)  Dinah Laurel Lance / Black Canary  - Batman and Black Canary apparently knock boots on numerous occasions.

Thrillkiller

 * 1) Barbara Gordon (Thrillkiller #2)
 * 2) Dinah Drake Lance / Black Canary (Thrillkiller ‘62)

Others
Various alternate futures presented in the Silver Age apparently depict Batman living happily ever after with Kathy Kane / Bawoman (specifics welcome)

Mary McClellan (Bruce marries her in an alternate reality where his parents survive) (LOTDK #76-#78)

The Batman (1943 Movie Serial)

 * 1)  Linda Page 

‘60s TV Series

 * 1)  Catwoman  - Although this version of Catwoman (played by three different actresses) is far more sinister than her comics counterpart, she still shares the same bond with Batman, an attraction that could be love if it weren’t for being on opposite sides of the law.

Burton/Schumacher Film Series

 * 1)  Vicki Vale - This version of Vicki, still a photojournalist, comes to Gotham to report on the mysterious Batman. She and Bruce have a wondrous first date, ending in them spending the night together. Bruce, devoted to his life as Batman, is disturbed over how much he is falling for her, and essentially ghosts her after that, appearing to be a rich playboy taking off after getting the booty call. After saving her from the Joker as Batman one more time, Bruce decides to tell her the truth about him, but is interrupted by another Joker attack. Finally, Alfred lets Vicki into the batcave. The two declare their love for each other before Bruce goes off to fight the Joker one more time. After a fight that ends up involving him saving Vicki again, and ends in the Joker’s death, the two embark on a relationship. They have broken up offscreen by between the first two movies however, because, as he states about his two lives, “She had trouble reconciling them because I had trouble reconciling them.”
 * 2)  Selina Kyle / Catwoman - This more supernatural (and psychotic) version of the character, is a lowly secretary for mogul Max Schreck, until she discovers his corrupt practices, and is murdered by him by being pushed out of a window. She is resurrected by magical cats chewing on her (yeah, never did make sense), complete with nine lives. As Catwoman, her main goal is to sabotage Scheck’s buildings. She flirts with Batman in costume while also co-conspiring with the Penguin to kill him. In her civilian identity, she reappears at Schreck’s office feigning amnesia. There she meets Bruce Wayne. and shares a date, and a passionate kiss, with him. They later discover each other’s identities, and Bruce attempts to get Selina to forgo her bloody vendetta against Schreck, but she apparently kills herself (ending her eight life) by electrocuting both herself and Schreck. After the ensuing explosion, her body is not to be found among the wreckage, and she is later shown to be alive, enjoying her ninth life.
 * 3)  Chase Meridian  - This woman is pretty sick. An abnormal pyschologist who has a thing for “the wrong man,” she comes to Gotham to consult on the ongoing Two-Face crimes, but is truly there because she is fascinated by Batman, and frankly, wants to bone him. She sneaks up to the rooftop of police headquarters with just a trenchocat over a nightie and lights the bat-signal to bring him to her with the intent of seducing him to apparently have sex right there on the police rooftop. He turns her down. She also meets Bruce Wayne and becomes friendly with him. Bruce falls in love with her, and when she manages to convince Batman to come knocking at her door, she turns him down because she is now in love with Bruce. She later discovers the truth about his identity, and at the end of the film, the two are in a relationship. Again, they apparently break up offscreen between films
 * 4)  Julie Madison  - In the fourth film, Bruce is in a long-term relationship with Julie Madison, who is unaware of his double life. She essentially proposes to him, but he says “I’m not the marrying type. There are things about me you wouldn’t understand."

DC Animated Universe

 * 1)  Zatanna  - Bruce is shown as having met Zatanna during his training to become Batman, the two falling in love before parting ways. The two meet up again after he has become Batman, even serving together in the Justice League, but the sparks never quite fly again.
 * 2)  Andrea Beaumont  - Bruce meets fellow child-of-wealth Andrea Beaumont just as he is preparing to become Batman, and the two fall in love. He appeals to the spirits of his parents, asking them to release him from the vow he made to them so that he can live a normal life and marry Andrea. But when her father is killed, Andrea becomes despondent and runs away. Years later, Batman attempts to stop a murderous vigilante known as The Phantasm, only to discover it to be Andrea, reaping vengeance for her father’s death. After a fight where he saves her from the Joker, she once again disappears.
 * 3)  Selina Kyle / Catwoman  - The same aspect of tension from the comics transfers to the series, but with one of the most definitive exchanges either character has been a part of.

“You can’t deny there’s something between us.”

“You’re right. And I’m afraid it’s the law.”

4.  Talia Al Ghul  - Again, their relationship happens essentially exactly as in the comics, with love for each other, but being kept apart by her devotion to her father and his evil ways.

5.  Lois Lane  - While visiting Metropolis, Bruce meets Lois Lane. The two are attracted, and begin dating. When she learns that he is Batman, she breaks the relationship off.

6.  Diana / Wonder Woman  - During their time together in the Justice League, Bruce and Diana begin to grow feelings for one another.

7.  Barbara Gordon / Batgirl  - The series Batman Beyond, taking place in the future, established that Bruce and Barbara did/would engage in a brief relationship at some point in the future of the main DCAU Any romantic tension between them in the present-day was not referenced until the direct-to-video Batman: Mystery of the Batwoman, right in the midst of his tension with Wonder Woman. In the film, Barbara somewhat aggresively flirts with Bruce over the phone. A flustered and resistant Bruce hangs up and denies other’s ideas that there is anything between them.

8.  Kathy Duquesne  - Although based on Kathy Kane/Batwoman from the comics, this technically-different character is the daughter of a mob-boss who begins to date Bruce. At the same time, he deals with a more lethal vigilante called Batwoman. He then realizes that Kathy is one of three women who have taken on the mantle of The Batwoman. For her, it is a way to take down her father, who she blames for the death of her mother. The three women’s identities are unveiled, and although Kathy avoids jail time, she and Bruce decide not to further pursue their relationship. (Batman: Mystery of the Batwoman)

So at this point, Bruce is basically beating off the women with a stick!

Later, the tension between him and Diana is finally addressed by the characters themselves. In the episode “This Little Piggy,” Diana lets him know that she wishes to pursue a relationship with him, and he resists for all the normal BS reasons (oh, if my enemies knew we were an item….)

It after this that he and Barbara begin a relationship. In comic books continuing the story, she even becomes pregnant with his child before experiencing a miscarriage.

Also in the DCAU comics, Julie Madison has a presence in Bruce’s life before turning out to be a gold-digger.

Batman Beyond shows a Bruce who, in the twilight of his life, is very much single.

Batman OnStar Commercials (hey, I’m counting it!)

 * 1)  Vicki Vale  - Batman calls Vicki Vale from the Batmobile to let her know he’ll be late for their date.

Birds of Prey

 * 1)  Selina Kyle / Catwoman  is described as Batman’s “one true love.” She gave birth to a daughter, Helena Wayne, apparently unbeknownst to him. He disappeared after some time, and Selina was killed by a mugger while out with her daughter (the killer later revealed to be Clayface.) Helena grew up to be the vigilante Huntress. At the end of the series, Alfred is seen talking to  Bruce on the phone, revealing Bruce is aware of Helena’s existence.

The Dark Knight Film Trilogy

 * 1)  Rachel Dawes  - Rachel’s mother worked at Wayne Manor when she and Bruce were growing up, and she and him were lifelong friends. As adults, her now working an assistant district attorney, they were clearly in love with each other, but were prevented from being together by Bruce’s troubled, detached psyche, which later caused him to leave town on his quest to train to be a vigilante. When he returns to Gotham, after everyone thinks he is dead, she believes him to be the irresponsible playboy he purports to be, but he later reveals his secret identity to her. The two share one kiss, and she admits her love for him, but states that Batman is a different person than the man she fell in love with, and that until Batman is no longer needed, they cannot be together.

She later begins dating new district attorney Harvey Dent. Although she is tempted by Bruce’s offering of himself to her, claiming that Batman’s days are near an end, she realizes that Bruce has still wholly become a different person than the child she grew up with, and accepts Harvey’s proposal. She is later murdered by The Joker. Also in this film, Bruce begins a relationship with Miranda Tate, who later turns out to be the villainous Talia Al Ghul, a much more devious version with no real love for Bruce and intentions to destroy Gotham City.
 * 1)  Selina Kyle / Catwoman  - In a more comics-accurate portrayal as a jewel thief, Selina starts off her acquaintance with Bruce Wayne by stealing his mother’s pearls, the ones that resulted in his parent’s deaths. He hunts her down and takes back the pearls, but does not turn her over to the police, and she plants a flirtatious kiss on his lips.

Selena also becomes acquainted with Batman, who she betrays to Bane to save her own skin, although she is visibly troubled by the decision. She learns Bruce’s true identity as she watches Bane call him "Mr. Wayne" and defeat him in a fight. When Bruce then returns from the exile Bane put him in, he still places his faith in Selina, seeing more in her than she sees in herself. She ultimately resists the temptation to save her own skin again and helps Bruce liberate the city, later saving his life by killing Bane. As Batman begins to sacrifice himself by flying away with the nuclear bomb Bane and Talia intended for the city, she kisses him.

Batman, and Bruce Wayne, apparently die in the incident. When it is later revealed that Bruce escaped the explosion, he is shown to apparently be in a relationship with Selina, with Alfred seeing them together at a French cafe, her wearing his mother’s pearls.

Batman: The Killing Joke (Movie)

 * 1)  Barbara Gordon / Batgirl  - Batgirl lusted after Batman in this controversial adaptation. This culminates during an argument, which ends in them kissing, in costume, before shedding the costumes and having sex on a rooftop.

DC Extended Universe

 * 1)  Diana / Wonder Woman  - In Justice League, Bruce and Diana clearly have some romantic tension between them, which Bruce comically denies to Alfred.

Others
''' Batman: The Brave and the Bold. '''The same basic relationship/tension exists between him and Catwoman.

 Batman: The Telltale Series  - Bruce and Selina have sex.

 Arkham -  His only romantic entanglement with Catwoman in the Arkham universe is playful flirtation on her part, although she does risk life and limb to save him from the asylum at one point.

Tension, past of present, with Talia, is referenced.

 Young Justice - Bruce is shown to have moved on long ago from a relationship with Talia