There are dozens of classic comic book couples that stand out as iconic symbols of various relationships. Superman and Lois Lane are a picture-perfect couple, Batman and Catwoman are symbolic of forbidden temptations, and Hal Jordan and Carol Ferris show the strain of superheroism on a working-class relationship. But notice how each of these relationships takes place between two consenting adults, none of whom are more then ten years in age difference from their partners. But for each iconic and perfect comic book couple, there’s one that leaves a sour taste in readers’ mouths. And a tell-tale sign of an uncomfortably bad couple is a sizable difference in age between the parties.

Apart from outright examples of controversial relationships in comics, there’s just something viscerally awkward about characters who are multiple decades older than their romantic partners. Now comics do have various workarounds, using mind control, de-aging, time travel, or any number of other confusing excuses to explain why such relationships are okay. But there are just as many times where writers were more than happy to let the pairing stand, or even pushed how uncomfortable they are to emphasize a character’s villainy. With that disturbing though in mind, here are fifteen comic couples with uncomfortable age differences.

15 DEATHSTROKE & TERRA

One of the admittedly few problems with the lauded "Judas Contract" story line was the heavily implied relationship between Deathstroke and Terra. After the latter betrayed the Teen Titans to the assassin, it was revealed that 15-year old Terra had been seduced by a man old enough to be her father.

And more than that, she seemed to be enthusiastic about it, often wearing uncomfortably revealing outfits around him and speaking mostly in double entendres. To make matters worse, artist and creator George Perez openly admitted that the goal of her design was to make her as young and sensual as possible, specifying that she was supposed to look 11. It’s definitely for the best that this little subplot was left out of the 2003 cartoon series.

14 CAPTAIN AMERICA & SHARON CARTER

Captain America, regardless of how he looks, is an 80-year old man. Sharon Carter, in current continuity, is no older than 40 -- and is still the grand-niece of Steve’s ex-girlfriend. And has lied to him constantly due to her line of work. And has faked her death and forced him to mourn her multiple times. And killed him after the first "Civil War" arc.

All while he has remained as straight-laced and all-American as ever, except for the "Secret Empire" storyline of course. Because to an octogenarian, anyone under 60 is a genuine catch. Also, Sharon stayed with him when he briefly lost his powers and finally started to look his age, so maybe the whole age disparity thing was what she’d signed up for.

13 ANGEL & HUSK

For one of the cornerstone characters as the franchise, Angel sure had some weird relationships, which is saying something considering the cavalcade of awkward X-Men romances. Perhaps his most outright offensive was his extended fling with the teenage Husk whom he dated while in his early 30s. The age difference alone would be bad enough, but the two also had one of the most grossly PDA relationships in comic history, so much so that even other X-Men were asking them to take it down a notch.

This culminated in a now infamous scene where the two strip and make out in midair while half the X-Men and Husk’s parents watch on in fascinated horror. Though the two have since broken up and Angel has even been de-aged thanks to time travel shenanigans, they still have expressed interest in each other, making the situation even more complicated and creepy.

12 DEADPOOL & COPYCAT

The 2016 Deadpool film would have you believe that the relationship between Wade Wilson and Vanessa Carlysle was between two damaged but loving adults that was born from a solicited date to an arcade. It was similar in the original comics, except Wade was a cold-hearted killer who didn’t exactly have a heart of gold and Vanessa was a shape-shifting teenage prostitute who went by Copycat.

Though the two fell in love and seemed to be legitimately happy together despite the age gap, their romance was short lived due to Wade’s cancer diagnosis and subsequent transformation into Deadpool. One of the weirdest part of their relationship was the visual aspect. It was explicitly stated that Copycat was underage, but she was consistently drawn as a grown woman, as if that would soften the blow.

11 BATMAN & BATGIRL

The critically acclaimed Batman: The Animated Series and following DC Animated Universe deserved all the praise it ever received, but there was a significant plot hole that none of the shows ever bothered to fill. In Batman Beyond, set in the DCAU’s future, Batman is completely estranged from his former family, including the now-adult Barbara Gordon who seems to harbor a particular hatred for her old mentor.

For years, it was a burning question in fans’ minds as to what broke up the batfamily. Finally, it was answered in the Batman Beyond comics. Turns out, a college-aged Barbara had cheated on her boyfriend Dick Grayson with the fully-grown Bruce and had gotten pregnant as a result. Against her wishes, he told Dick everything. And then she miscarried. So yeah, now she hates him. Fair enough.

10 WOLVERINE & JEAN GREY

Marvel seems to have a strange obsession with having characters that are decades older than they look. Captain America, Black Widow, and Winter Soldier are all in their 80s and have all dated much younger thanks to various super serums. But none of them top Wolverine who, at 140-years old, has had an on-and-off relationship with the college-aged Jean Grey for almost 40 years’ worth of comics.

It makes sense in a way, Jean Grey always represented the good-girl-gone-bad archetype and Wolverine is nothing less than the epitome of perceived masculinity. Both would become a symbol for the other of realizing and overcoming their personal flaws and traits. But there’s still a 120-year difference between the two and there’s no way to ignore the awkwardness there.

9 WOLVERINE & SQUIRREL GIRL

A common trait amongst Wolverine’s ex-girlfriends is that they all seem to end up dead. While the Unbeatable Squirrel Girl has thus far escaped such a fate, she is still counted among their number. Though never openly stated, it is heavily implied that the century-and-a-half-old Wolverine had a hook-up with a teenage Squirrel Girl. She holds a permanent spot in his mental girlfriend fantasies and their reunion at Avengers Mansion was tellingly awkward, with Wolverine even saying that they’d agreed never to see each other again.

At the time of their second meeting, Squirrel Girl had recently turned 20 and it was hinted at that their first encounter had happened five years previously, when she would have been only fifteen. And thus, Wolverine instantly became less of an unstoppable warrior and more of a creepy old man.

8 NORMAN OSBORN & GWEN STACY

Gwen Stacy Norman Osborn

One of the worst retcons in not just Marvel Comics but in the history of the medium was the establishment of the secret relationship between Gwen Stacy and Norman Osborn. Revealed in flashbacks during the "Sins Past" storyline, it turns out that while in high school, Gwen Stacy was regularly hooking up with her classmate’s billionaire father and future super villain Norman. Their consistent meetings resulted in her getting pregnant with twins.

Gwen gave birth to them in secret and immediately abandoned her children in Europe to keep them away from their sociopathic father. The obscene nature of their relationship was only emphasized by sketchy art that showed close-ups of Norman’s creepy leer hanging over, presumably, Gwen’s body. You will never get it out of your head. Sorry.

7 MAGNETO & ROGUE

Magneto and Rogue in Marvel Comics

The "Age of Apocalypse" storyline bolstered the X-Men legacy, gave writers a new universe to shape and draw from, and inspired one of the worst X-Men movies. It also introduced the concept of Magneto, a 60-something man with adult children, pairing up with Rogue, a woman half his age. To make matters worse, their matchmaker was Scarlet Witch, Magneto’s daughter and Rogue’s best friend, who, on her deathbed, requested they stay together. Rogue followed Wanda’s final wish and became Magneto’s confidant.

Eventually they developed feelings for each other, despite their 30-some-year age difference. Oh, and also Rogue had permanently absorbed the powers and memories of Polaris, another of Magneto’s kids (or something). So Magneto basically married and had a child with a variant of his youngest child who came recommended by his oldest daughter. And they say comics are for kids.

6 ANGEL & X-23

Angel has been an iconic X-Men since his introduction with the original line-up in 1963. Despite being in print for the better part of 60 years, the un-aging, time-traveling, and overall convoluted nature of comics means that Warren Worthington III is actually only in his mid-30s in the comics. X-23 was introduced for the first time in the X-Men: Evolution cartoon in 2003.

She’s been in comics for a little over 15 years now and is suitably young in-universe, only around 20 years old. To their very little credit, when they briefly date it was when Warren had come from the future as an older teenager, around 18. So a 30-something dude in a teen body dated a young adult clone of one of his adult friends. The math alone in that equation is mind-boggling.

5 HAL JORDAN & ARISIA

arisia-and-hal-jordan-in-bed

Arisia was a humanoid, teenage Green Lantern with a deep infatuation with Green Lantern Hal Jordan. The only problem: Hal was a grown man with certain hang-ups about dating a girl less than half his age. Fortunately, Arisia had the perfect solution. While temporarily trapped in a cave with Hal, she confessed her feelings to him and, when he informed her of his hesitancy, she used her ring to forcibly age her body into a full-grown woman while keeping her teenage mind.

And that was pretty much all it took for Hal to be onboard with the idea. The two dated for some time but eventually broke up due to, of all things, a perceived imbalance of power. Not long afterwards, Arisia hit her head and reverted to her teenage self. Comic book logic at work, ladies and gentlemen.

4 DR. MANHATTAN & SILK SPECTRE

Alan Moore’s Watchmen is one of the quintessential graphic novels, a critical work of visual literature that could singlehandedly validate the medium as an art form. On an analytical level, the strained romance between the atomic deity Dr. Manhattan and the reluctant young hero Silk Spectre is meant to represent Dr. Manhattan’s gradual loss of humanity. On a surface level, it’s an omnipotent middle-aged nudist hooking up a 16-year old girl who really doesn’t want to be a superhero.

Also, he was cheating on his long-time partner who’d stuck with him through his ascent to nuclear-godhood and put up with his clairvoyant antics. Though this was ultimately a device to demonstrate that even all-powerful entities are fallible, it still stood out as wildly inappropriate, which was probably the point. This is Moore after all.

3 CLOCK KING & DISRUPTOR

clock king

The "Terror Titans" story was a lot of things. PC was not one of them. A major subplot involved the grown mastermind Clock King manipulating and sleeping with the teenage Disruptor so as to better control the social aspects of his team of juvenile supervillains. Even if there weren’t a good 20-year age difference between the two, their relationship was built solidly in exploitation and abuse.

Clock King openly admitted he was using Disruptor’s psychological hatred of women and pathological need to please men to get what he wanted from her, which was made abundantly clear in the near-explicit scenes of the two of them post-coitus. To make matters even worse, Clock King was using his relationship with Disruptor to turn her against Ravager, who he was also trying to sleep with.

2 CYCLOPS & MADELYNE PRYOR

Nobody in comics has a weird history of relationships like Cyclops. His bland but important relationship with teammate Jean Grey has been a defining element to both of their characters, but her multiple deaths and resurrections have given him ample time to play the field. The most uncomfortable of his in-between-jean trysts was with Madelyne Pryor, a woman who looked exactly like Jean because, shocker, she was a clone.

Not only had her body been speed-grown by Mister Sinister, but she hadn’t technically been alive until the real Jean died and a portion of the Phoenix force latched itself to Madelyne. So she had only been ‘alive’ for a few weeks when Sinister arranged for her to meet Scott in Alaska, and she was less than a year old when she gave birth to baby Cable.

1 DONNA TROY & TERRY LONG

Anytime someone wants to defend the integrity and validity of the comic medium, someone could debate them by pointing out that Donna Troy and Terry Long were a couple for several years and dozens of issues before anyone at DC realized what a terrible idea it was. While she was a member of the Teen Titans, Donna attended a nearby college where Terry worked. He was a grown adult man. She was his 19-year-old pupil. Despite all logic, the two began to date and even got engaged while still in a student-teacher relationship.

Then they had a kid because the world is cruel and cold and DC writers were apparently oblivious to how creepy this all looked. Oh, and Terry was an absolute perv who openly hit on Donna’s teammate Starfire while his fiancé was in the room, something Starfire was into because, again, cold, cruel world.