Clark Kent / Superman

Earth-Two

 * 1) Lois Lane  - The Golden Age Superman is shown to only have eyes for Lois Lane. He played the goofy, clumsy nerd as her co-worker Clark Kent, while she swooned at Superman. She would often suspect the two were one and the same, but he would always find a way assuage her suspicions.

It was revealed that later, he revealed his dual identity to her, and the two were married (Action Comics #484, Jun. 1978). Although fully grown, Power Girl became a surrogate daughter to the couple.

When Earth-Two was destroyed in the Crisis, Clark, Lois, and Power Girl were the only three survivors. Clark and Lois went off to live with Alexander Luthor and Superboy-Prime in an alternate dimension Luthor had created, where they watched the new world of heroes grow.

Eventually, that world took some dark turns, with heroes making some questionable decisions. Lois began to grow ill, and Clark attributed her illness to the growing darkness in the outside world. He concocted a plan to try and change the reality of that world with Alexander and Superboy. Before he could accomplish anything, Lois died. He later learned that Alexander and Superboy had made Lois sick, in a scheme to have Superman help them change the world to their liking. He then battled Superboy Prime in a fight that resulted in his death.

In the aftermath of the Crisis, it was discovered there was a new Earth-Two in the new multiverse, with its own version of Superman with apparently identical history to this one. Although this version has been missing for a few years, he is presumed alive. However, there is no word on the status of Lois Lane in this timeline.

(later stories showed that there was in fact an Earth-Two version of Lana Lang, one that did not grow up with Clark but met him as an adult. I don’t think there was ever a romantic involvement teased)

Earth-One / Post-Crisis / New Earth
Earth-One - Like Lois Lane, Lana Lang would often suspect that Clark and Superboy were one and the same. She would grow into adulthood without learning the truth.
 * 1) Lana Lang - Clark Kent’s childhood friend and first love was Lana Lang, a fellow student at Smallville High School as well as serving as Superboy.

 Man of Steel  - In this version, and in all future ones, Clark did not serve as Superboy in Smallville. it seems that the romantic attraction here was largely one-sided, with Lana pining for Clark. Upon high school graduation, he revealed his powers to her before leaving town.

Birthright - This rewrite of his origin shows Clark and Lana to have had a mutual romantic relationship during their youth. At the start of the storyline, Lana has already left Smallville prior to Clark's return from his world journey. Upon his arrival home, Clark is told that Lana left some time prior and has not been heard from since. Following this storyline, there is never again any mention of her history regarding Clark or Superman. (I’m unsure if she knows about his abilities/identity in this version, but I will assume she does, as that would ensure continuity with the other Post-Crisis stories)

New Earth - Lana's romantic relationship with Clark was often interrupted by her two obnoxious brothers The two shared at least one kiss as children, the hormones created by it sparking Clark's first experience with heat vision. (as for whether she knows his identity, the same thing I said for Birthright applies.)

Lisa Davis was also a student at Smallville High who bore feelings for Clark, though no evidence has been found that he returned those feelings.  Earth-One  - Lori was Clark’s college sweetheart before he discovered she was a mermaid, and had to go back to the sea.  Post-Crisis / New Earth  - A new version of this story was told, with Clark not yet having taken up the mantle of Superman. In Post-Crisis stories, Clark is shown to act much more competently, without so much of the nerdy persona, functioning more as Lois' equal.
 * 1)  Cleopatra , the time-travelling ancient queen of Egypt, and Superboy once fell for each other before she returned to her own time. (Adventure Comics #291). This history was eliminated in the Post-Crisis and New Earth versions.
 * 2)  Lori Lemaris  -
 * 1) Ruby Carson worked at a restaurant with Clark when he first moved to Metropolis. The two became good friends, and went on a few dates.(World of Metropolis #3, Oct. 1988)
 * 2)  Simone D'Neige  was an early reporting mentor and girlfriend of Clark's.
 * 3) Lois Lane and Clark had much the same relationship as their Earth-Two counterparts. He was a nerd, and she loved Superman, but she was often trying to prove that he and Clark were one and the same.
 * 1)  Lyla Lerrol  was a famous Kryptonian actress. Superman met her when he time-traveled to Krypton before its destruction.(Superman #141, Nov. 1960)

Lana Lang then moved to Metropolis as an adult, becoming a reporter alongside Clark Kent and Lois Lane.

In Earth-One continuity, she became a major competitor for Superman's affections, being similarly in the dark about his true identity. In all Post-Crisis versions and New Earth, she was privy to his secret.
 * 1)  Luma Lynai -  Supergirl tries to find a mate for the lonely Superman. After match-making attempts with Helen of Troy and an adult Saturn Girl fail, Supergirl uses the computer in the Fortress of Solitude and discovers a super-powered woman on the distant planet of Staryl named Luma Lynai.

Superman flies to Staryl and the two heroes immediately fall in love. Unfortunately, Superman discovers that Luma Lynai's powers only work under the rays of an orange sun; Earth's sun yellow rays are as deadly to her as kryptonite is to Superman. Luma, realizing that Earth needs Superman, tells him he must leave. (Action Comics #289, Jun. 1962)
 * 1) Sally Selwyn became romantically involved with a man named "Jim White", who was actually an amnesiac Clark Kent. After Jim seemingly died, Sally was heartbroken. (Superman #165, Nov. 1963)
 * 2) Orella - Superman is trapped on an island of Amazons from another planet and forced to face Orella, one of their number, in three tests of strength--all of which he loses. For his loss, Orella insists he marry her. (Superman #180, Oct. 1965)
 * 3) Lyrica Lloyd - An actress to whom Clark revealed his secret identity to and proposed to, before she apparently died. (Superman #196, May 1967)
 * 4) Althera - An Amazon from another world with whom Clark, as Superman, once fell in love.(Action #395 Dec. 1970)
 * 5)  Barabara Gordon / Batgirl  and Clark Kent, without knowing each other's secret identities, went on one date while she was a congresswoman and he was visiting Washington, DC.

While an amnesiac on the planet Apokalips, Superman was swayed by the hypnotic powers of the evil Amazing Grace to join her. He even possibly had sex with her before returning to his normal self. (Adventures of Superman #426, Mar. 1987)
 * 1) Diana / Wonder Woman

Post-Crisis - Shortly after arriving in Man's World, she and Superman had a first date, which is done mainly for publicity reasons. Superman planted a kiss on her, but this startled her, as it was not what she had in mind, although she does admit to being attracted to him. After having an adventure together, the two decide to remain just friends. (Action Comics #599-600, 1988).

 New Earth  - Wonder Woman arrived six years earlier, around the same time Superman does, so it’s unclear if a version of this story still meant to be in continuity.
 * 1) Cat Grant - Clark briefly dated this fellow reporter. Clark had sex with Amazing Grace (Adventures of Superman #426, Mar. 1987) Eventually, Lois lets go of her crush on Superman and begins dating Clark. He reveals his dual identity to her at the same time that he proposes. She accepts, (Action Comics #662, Feb. 1991)
 * 2) Lola-La - While an amnesiac on a tribal island, Superman almost married the chief's daughter. (Superman: The Man of Steel #6, Dec. 1991)

Simone D'Neige eventually came to work for the Daily Planet, and her past relationship with Clark did not sit well with Lois (Adventures of Superman #40, Oct. 1994)

and they are later married. Lana eventually marries her and Clark's childhood friend Pete Ross, and they have a son named Clark. Pete becomes vice-president, and later president, making Lana First Lady. During that time, however, the two divorce, and on a visit to Clark’s parents, she confesses that she is still in love with Clark, despite the fact that he is still married to Lois.

Terri Chung (Superman: The Odyssey, 1999)

In one story, Superman and Wonder Woman were thrown into an alternate universe where they were forced to slay demons for a thousand years. After some time, Diana apparently proposed a romantic relationship, but Clark remained committed to his marriage. (Action Comics #761, Jan. 2000)

New 52

 * 1)  Lana Lang  - Lana was still a factor in his youth. I'm not sure about Lori, though.
 * 2) Lois Lane - There remains the same essential romantic tension with Lois.
 * 3)  Diana /  Wonder Woman and Superman became an item. It’s here that for the first time, at least in the comics, an unwed Clark is shown getting his freak on.

Superman-Red and Superman-Blue

 * 1)  Lana Lang & 
 * 2)  Lois Lane  In this imaginary story, a freak accident splits Superman into two bodies. The twin Supermen initially seem to be exactly alike, until they start discussing marriage. Superman-Red says that although he thinks of his time with Lana fondly, the true love of his adult life is Lois Lane. Superman-Blue says that while he cares for Lois, nobody can measure up to his first love, Lana Lang. And thus both Supermen get married in a joint ceremony, and all four live happily ever after (Superman #162, 1963)

The Dark Knight Returns

 * 1)  Diana /  Wonder Woman and Clark had a superpowered daughter called Lara, after Superman's Kryptonian mother, whom they protected from the government.

Kingdom Come

 * 1)  Lois Lane  - Clark was very much in love with Lois, who died tragically when the Joker unleashed a poison gas on the Daily Planet.
 * 2) Diana / Wonder Woman - Clark then enters into a relationship with Wonder Woman, with whom he has a child, Jonathan Kent..

Superman: Distant Fires

 * 1) Diana / Wonder Woman - On a post-apocalyptic Earth where Superman and Wonder Woman were among the only survivors, they had a son who, like Kal-El, was eventually rocketed to another planet to save him from his homeworld's destruction.

Red Son

 * 1)  Wonder Woman 

All-Star

 * 1) Lois Lane - Lois remains the central love interest.
 * 2) Wonder Woman

Adaptations
Clark is shown with the same typical relationship with Lois (they’re co-workers, and as Superman he saves her a lot) in the radio show, the Fleischer cartoons, the 1948 and 1950 film serials, the 1950s television show, and any animated television version, although romance is not typically a focus in this early material. The same relationship also permeates any direct-to-video animated film.

Initial Film Series

 * 1) Lana Lang - Lana is shown to be Clark’s high school crush.
 * 2) Lois Lane - Clark immediately falls for Lois after moving to Metropolis. She immediately falls for Superman. As Clark, he manages to get her to go on a date with him, but also arranges it so this happens immediately after she has an exclusive interview, and takes a romantic flight, with Superman, something she is still flustered by. As he picks her up for their date, Clark almost reveals his true identity to her, but thinks better of it, and keeps up the facade. Nothing about dating is talked about between them again. ("Superman")

Lois later learns his true identity, and the two form a relationship. Clark is told by the essence of his mother (his father in the alternate cut) that if he wishes to be with a human, he must become a human. Using the Fortress of Solitude’s technology, he does so. But when the Kryptonian villains, Zod, Ursa, and Non attack Earth, he is forced to gain his powers back to stop them. After this, he and Lois realize they cannot continue in their relationship. Using a bizarre new power, Clark kisses her and, through the kiss, erases her memory of his true identity and their time together. (in the alternate cut, this is done by reversing time) ("Superman II")

Clark goes back to Smallville for his high school reunion and strikes up a friendship with Lana Lang again. This friendship smacks of the romantic, in spite of what he learned about such things recently ("Superman III").

Clark later finds himself the object of the affections of Lacy Warfield, the daughter of the Daily Planet’s new editor, and humors her with a date. Shortly after, he reveals his identity to Lois again, jogging her memory of their time together, before he once again erases her memory with a kiss.

Superman Returns (Earth-96)

 * 1) Lois Lane - (The film Superman Returns, later said to be on this world, follows up a similar version of events to the first two films while at first appearing to ignore the events of the third and fourth, though the events of the third are later referenced.)a

After astronomers discovered what they thought to be remnants of the planet Krypton, Clark took a space ship there on a long journey to see if it were true, but only discovered the dismal remains of this planet. He returned to Earth after a five-year-long absence to find a Lois who was resentful of him, was now engaged, and has a five-year-old son with her fiance. After having another interview, and another romantic flight, her anger mellowed. It was later revealed (presumably surprising even Lois) that her son, Jason, is actually Superman’s son

(This is presumably from their time together during Superman II, though the later reference to the events of Superman III seemingly mitigate this, meaning another romantic liaison must have happened).

While Superman later lie in a coma, Lois whispered the truth in his ear before giving him a kiss. After he awakens, Lois was still with her fiance, but the future remained ambiguous ("Superman Returns")

Lois and her fiance eventually split up, Clark revealed his secret identity to her, and they were married. Lois was killed, along with Perry White, Jimmy Olsen, and many others, when the Joker dispelled a poisonous gas on the Daily Planet. After that, Clark began wearing an altered version of his chest emblem, with a black background.

After the reality-altering events of the Crisis on Infinite Earths, Superman was shown flying with a yellow background to his emblem, possibly meaning that his timeline had been altered to avoid his loved ones' unfortunate fates. ("Crisis on Infinite Earths")

Lois & Clark: The New Adventures of Superman

 * 1)  Lana Lang  is once again shown to be Clark’s high school girlfriend.
 * 2)  Lois Lane  - Clark claims to have loved Lois from the first time he saw her. For her, the attraction took longer to build, but they become partners and best friends. During this time, Clark often fights off the advances of fellow reporter Cat Grant, in whom he has no interest. At the end of the first season, she is preparing to marry Lex Luthor. To stop her from marrying a man whom he knows to be evil, Clark confesses his feelings for her. She does not reciprocate, but as the wedding approaches, finds herself fantasizing about marrying Clark instead. She is about to call the wedding off when police arrive to arrest Lex. Later, she seems about ready to tell Clark of how she feels, when he tells her, lying, that he did not mean what he said, and that he would have told her anything to stop her from marrying Luthor.
 * 3) Mayson Drake was a police woman who had a strong attraction to Clark from the start. Clark only mildly reciprocated, and went on a date with her.

Clark eventually asked Lois out on a date, and she accepted At the end of it, they shared a kiss They just so happened to be in close proximity to where Mayson was, who, at that moment, was killed by a car bomb. As Clark held the dying Mayson in his arms, she caught a glimpse of his Superman costume beneath his clothes, and knew the truth just before she died.

Clark and Lois eventually dated, fell in love, and became engaged, with her learning the truth about his identity. Clark mentioned that when he told his old girlfriend Lana Lang about the wedding, she invited herself. Lois at first had trepidations about Lana attending the wedding. She then was transported to an alternate universe, one in which Lois was dead, and Clark never debuted as Superman, and was now engaged to Lana, who encouraged him to keep his powers hidden. Lois convinces him to become the superhero he is meant to be, and he and Lana break up. After returning to her own reality, Lois realizes what a bad match Clark and Lana were and now has no problem with her attending the wedding.

Clark and Lois were married and spent the rest of the series as a married couple.

DCAU

 * 1) Lana Lang - As usual, Lana is portrayed as Clark’s first love from Smallville.
 * 2) Lois Lane - Clark is portrayed in his more normal, less nerdy persona in this version, but he and Lois  never have any real romantic tension while in this guise, only when he is Superman.

Lana is then shown as now being a successful fashion designer. She comes back into Clark’s life and comes on to him hard. The two share a kiss, but they do not pursue a relationship (I’m pretty sure she knows he’s Superman in this version)

In spite of still not knowing the truth about his identity, Superman and Lois are shown having a picnic together and even kissing. What exactly their relationship-status would say is unclear. ("Justice League")

Smallville

 * 1) Lana Lang - Clark is infatuated with the girl next door. Freshman year, they become friends, but any romance is inhibited by the fact that she is dating senior Whitney Fordman.
 * 2) Chloe Sullivan - Clark later learns that his best friend Chloe Sullivan has feelings for him, and he begins to reciprocate. Clark takes Chloe to a dance while Lana sees Whitney off as he joins the military. Just when Clark and Chloe are about to kiss, a tornado strikes, and he runs off to save Lana.

Clark saves Lana from a tornado, something which seemed impossible, and leads to her knowing he is keeping secrets from her, a constant chagrin to their relationship. Nevertheless, throughout sophomore year, he and Lana experience heightened romantic tension. Lana eventually breaks up with Whitney, who is later killed in action. Whatever there was between Clark and Chloe cools, and in spite of his earlier response to her feelings, from this point on he maintains he does not return her feelings for him.
 * 1) Kyla Willowbrook - After discovering a series of Native American caves detailing a story eerily similar to his own, Clark’s powers are discovered by  Native American girl Kyla Willowbrook. She and Clark begin dating, him believing she may be the soul mate that is predicted in the cave paintings. There is even a special bracelet that the mythic figure is supposed to give to said woman. Kyla hides the fact that she has the power to turn into a wolf, and is attacking city officials to keep them from desecrating Native American land. While attacking Lex Luthor, she jumps out of a window and is wounded by the glass. Clark discovers her in human form, and she dies in his arms. Her grandfather gives Clark the bracelet for his true soul mate (Despite this, the bracelet is never seen again).

Some time later, Clark and Lana finally become a couple. Soon after, Clark becomes distraught over having accidentally caused his mother to miscarry her child, and runs off to Metropolis. After returning at the end of the summer, he tells Lana their relationship will "never work."
 * 1)  Alicia Baker  -  Junior year, Clark meets fellow student Alicia Baker who, like many residents of Smallville, has superpowers brought on by the Kryptonite in town. She has the power to teleport. The two begin dating, but she soon turns out to be unstable and insane. After attacking Lana, she is locked up in a mental institution.
 * 2) Lois Lane - Chloe’s cousin first comes to Smallville near the beginning of Clark's senior year to investigate Chloe’s apparent death, which turned out to be faked. She first met Clark when she found him in a corn field, naked and suffering from amnesia, believing him to be struck by lightning (the actual explanation was much more complicated). At first, their relationship had no inkling of romantic tension, Clark stating "She's bossy. She's stuck up, she's rude, I can't stand her!" Lana, however, stated her prediction of the two's coming together.

Senior year, Alicia is released from the institution, and, believing her to be cured, Clark renews his relationship with her. She still shows signs of instability, however, dousing him with the mind-altering red kryptonite, and having him take her to Las Vegas to have a non-legal wedding. Afterward, Clark forgives her, and they continue to date. She reveals his secret to Chloe, believing that he needs her to know. Later, Alicia is murdered by a villain.

At the end of senior year, after multiple boyfriends turn out to be evil psychopaths, Lana and Clark renew their relationship, but with him still hiding his secret from her.

At the beginning of their freshman year of college, Clark and Lana lose their virginity to each other. But once again, the fact that he remains secretive is a barrier, and they eventually break up.

In the midst Clark running off into battle, believing she may never see him again, Chloe kisses him. Clark even seems to respond for a few moments, but they do not pursue a relationship, and Clark does not give any later sign that his feelings about Chloe have changed.

Lana eventually falls for Lex Luthor. Clark can see that his former friend is becoming more and more evil, but Lana will not listen to him. Lana eventually finds that she is pregnant, and marries Lex. She later discovers that the pregnancy was faked by Lex to get her to marry him. As she prepares to leave Lex, she witnesses Clark using his powers, finally learning the truth.

After faking her own death and returning, Lana and Clark enter their third relationship, eventually living together in the farmhouse, after his father has died and his mother has moved away. Their relationship is strained, however, when a phantom from the Phantom Zone imitating Clark (Bizarro) has sex with Lana, and Clark believes that she should have known that this was not him.

Clark and Lana’s relationship is only brought to an end, however, by a vengeful Lex, who douses Lana with Kryptonite, so that it permanently remains in her system, making her unable to even approach Clark for the rest of their lives.

Clark and Lois eventually grow closer, working together at the Daily Planet. They finally form a relationship, and Clark reveals his secret to her.

(On one occasion, Clark finds a picture of Lana and, smiling, puts it away, a sign on the writer’s part that he has moved on.)

Clark eventually proposes to Lois, and she accepts. Unique to this version, not only does she know his secret before he becomes Superman, she even helps him assimilate the glasses-wearing, nerdy-persona of the new Clark Kent.

Clark and Lois’ wedding is botched by the invasion of Darkseid, in which he finally debuts as Superman to the public. Seven years later, for some reason, they have still not gotten married, and are only then preparing for their wedding later in the day. ("Smallville")

Just two years after that, the two are shown living at the farmhouse with at least two young daughters. Clark has somehow given up his powers, no longer serving as Superman. ("Crisis on Infinite Earths") 

Superman: Doomsday

 * 1) Lois Lane and Superman have begun a relationship, despite not her not knowing of his identity as Clark Kent. Superman apparently dies at the hands of Doomsday and is mourned by Lois. When he returns to life, he reveals his true identity, and the two embrace.

Injustice: Gods Among Us

 * 1) Lois Lane - The death of Lois Lane in this version sends Superman over the edge, turning him into a despotic tyrant of Earth.
 * 2) Wonder Woman

DCEU
Lana is shown to be Clarks’ childhood friend, but no romance is mentioned.
 * 1)  Lois Lane  - Lois investigates a Kryptonian ship and is injured by one of the robots working on it. She is saved by a pre-Superman Clark, who was investigating his past, and who uses his heat vision to cauterize her wound. Lois later sets out to find her rescuer, eventually identifying him as Clark Kent, just before he debuts as Superman. Just after his first adventure, they kiss and begin a relationship. ("Man of Steel")

Years later, the two are living together. Clark is killed by Doomsday, and his mother reveals to Lois that he was planning to propose. Lois begins wearing the engagement ring he planned to give her. ("Batman v Superman: Dawn of Justice.)

Clark is later resurrected by the Justice League, and he and Lois are happily engaged. ("Justice League")

Arrowverse
 
 * 1) Lois Lane - Clark is shown to be in a happy, long-term relationship with an offscreen Lois. He still has to avoid the constant advances of Cat Grant whenever he sees her. The two eventually have a son together, Jonathan. However, after the reality-altering events of the Crisis on Infinite Earths, time has been changed so that now the two are the parents of two adolescent boys, Jonathan and Jordan.