In all her 80 years of existence, there has been one constant in the characterization of Lois Lane – she really, really likes Superman. Still, due to editorial mandate over the last several decades (which often preferred an unmarried hero), Superman has had the poor girl bouncing around all over the universe, trying to win his often quite dubious hand in marriage.
Currently, as part of the company-wide relaunch at DC called Rebirth, Lois has finally gotten the guy; she and “Smallville” are married with a son. On the other hand, Lois has been around for 80 years. Plenty of times, she and Superman were split up, sometimes for years. While the Man of Steel was off doing things like dating Wonder Woman and being in the Justice League, Lois was left to her own devices, and we found out that she has generally really terrible taste in men. There's been some ups and downs for Lois and Clark, but, generally they're just better off dating each other—because everyone who dates Lois tends to get murdered, or forgotten about, or both.
On the other hand, one time she made out with the entire Justice League, so the girl's got options.
In the late 1980s during one of DC's many company-wide retcons, we were introduced to a deeply career-oriented Lois who was dating a man named Jose Delgado. It turned out that Jose moonlighted as a Judge Dredd-esque grim and gritty vigilante by the name of Gangbuster. Guess what he hated? Gangs. Despite his righteous fury about, well, everything, Jose didn't have an easy life. He was nearly paralyzed after saving Lois Lane's life from a robot named Combattor (named by Lex Luthor, who everyone keeps telling me is a genius, but when he throws out names like that I have to wonder). An amnesiac Superman even stole his costume for a little while, which was pretty weird. After his relationship with Lois fizzled, he went on to briefly date Cat Grant and then pretty much vanished into the ether. In all fairness, even though he didn't have a lot of strongly defining characteristics he was still cooler than most of Lois' non-superhero boyfriends.
It's often been hinted that Bruce Wayne is attracted to Lois, and it makes sense that he would be. She has a lot of the same characteristics of one Selina Kyle, Catwoman extraordinaire. They're both driven, career-centered investigators, and both are strong enough personalities to hold their own while in a room with god-like heroes and villains. Meanwhile, Bruce represents a mysterious dark side for Lois that she doesn't often see in her usual steady, Superman. Throughout the Silver Age, there were several campy fake engagements and “imaginary stories” between Bruce and Lois, usually with Superman looking shocked and crying on the cover—only for readers to discover it all to be an elaborate prank in the end. Perhaps the best known dalliance between Lois and Bruce was in the World's Finest episodes of the Superman animated series in 1997. While they have a drawn-out flirtation over the story, she ultimately discovers he is Batman and resents him for keeping the truth from her. We also find out here that she doesn't like Gotham and refuses to go there to be with him. They break it off, and Lois, as usual, ends up with Clark, although not officially until a couple years later at the wrap of the series.
We all knew we were never going to be down with whatever new boyfriend Lois Lane was going to have in the New 52. DC broke up the beloved marriage of Lois and Clark by giving us a new world in which the two had never been involved. During this time, Superman dated Diana, Princess of Thymiscira, so he was fine. Lois, on the other hand, dated one of the most obnoxious and willfully forgettable characters in the DC pantheon, Jonathan Carroll. Almost as if to prove a point that they knew fans were going to dislike him, DC really went all out in making Jonathan kind of the worst. Not only does he show up naked in Lois' apartment without any nipples (I'm guessing they were lost in inking? Or maybe he just forgot to have nipples?), but he was also way too smug and annoying for fans—or Lois—to really hang on to him. In his last appearance, Lois ever so slightly erased his memories for no apparent reason. Jonathan Carroll has yet to pop up again, and everyone seems pretty cool with that—including Jonathan.
In Superman's Girlfriend Lois Lane #18, Lois' car just stops working while she's driving through the middle of the desert. Without taking the time to explain why the hell Lois is there to begin with, the art immediately depicts a spaceship falling from the sky. Lois jumps right aboard and gets rocketed into outer space. Out of a psychedelic color swirl Astounding Man emerges, immediately telling Lois that he's in love with her. He not only proposes, but also assures her that there's no chance Superman will ever propose to her. Because Lois apparently just really wants someone to propose to her, she agrees to go with him to his home planet of Roxnon. Astounding Man takes Lois on a tour, showing her his dozens of paintings and statues of her as well as his “Lois Contemplation Room,” a room in his house where he goes to contemplate Lois and watch videos of her. So, pretty run-of-the-mill stuff for a first date. Astounding Man somehow manages to win Lois over with this and she agrees to marry him—until she's brought into a secret room and and sees a tiny old man hunched over a remote control, who introduces himself as Oogamooga. Turns out he created Astounding Man, who is actually a robot made of chemicals, and controls his every move from his Howard Hughes-esque laboratory. Lois decides that the easiest way to handle the whole situation is to make a similar duplicate of herself and find an equally creepy older lady to operate it. So somewhere in the universe, there are two creeps enacting a marriage between two robots, one of which looks like Lois Lane. Romantic, no?
Honestly, Lois Lane kind of hangs out with Satan too much. This time around, in Superman's Girlfriend #103, we are treated to a torrid tale of a very Satan-like alien who falls in love with Lois Lane from all the way out in space. I read this issue three times trying to figure out exactly what's going on, but it more or less boils down to this: Superman thinks he killed Lois, and he proposes to her corpse. Neat! In a comic that primarily built its last 100+ issues on this guy emphatically refusing to propose to marriage, he waits until she's dead and then finally goes for it. Lois ends up with devil's horns and a Satan-esque husband-to-be, and then... doesn't. She just kind of bounces. Like I said, it's not the most coherent story but it is highly enjoyable. In other news: Lois! Stop hanging out with Satan all the time! Definitely stop accepting contractual agreements and wedding proposals from him!