No Superhero Has More Tragic Love Interest Deaths Than This One
One particular occupational hazard for superheroes is that they tend to lose romantic interests no matter what. Daredevil's (Charlie Cox) MCU timeline features the death of Elektra (Élodie Yung), which is also a significant event in the comic book character's story, too. Spider-Man is known for rarely catching a break, most infamously when it comes to the tragic history of Gwen Stacy.
However, the major superhero with the greatest number of love interest losses is neither of these characters, but an X-Man who has quite a few decades of dating under his belt — namely, Wolverine. Various versions of James "Logan" Howlett have lived through at least 10 prominent love interest deaths that we know of, with others no doubt waiting in the wings.
On the DC side of things, Batman gives Wolverine some competition. The list of his dead love interests in the comics include Amina Franklin, Dawn Golden, Jezebel Jet, a version of Kathy "Batwoman" Kane, Natalia "Nocturna" Knight, Natalya Trusevich, Silver St. Cloud, and Vesper Fairchild. He also shared a mutual budding attraction with the New God Bekka, who was killed soon after they met. There's also a version of Poison Ivy who seemingly dies in "Batman: Gotham Knights" issue 65, but the fresh vines on her gravestone all but state that she'll be back.
Wolverine is old and gets around a lot
Canonically, Wolverine was young in the late 19th century, which means he's been in the dating pool for well over 100 years. As such, it's no surprise that he's had his share of tragic losses, especially when you take his dangerous lifestyle into account.
Logan's major losses include Rose O'Hara, who was accidentally killed by young James Howlett himself during a fight with Dog Logan. Silver Fox and Native were both killed by Wolverine's archnemesis, Sabretooth. Wolverine's son and Daken's mother, Itsu, died by the hand of Bucky Barnes during his Winter Soldier days. Logan's WWII-era flame Atsuko died in the U.S. atomic bombing of Hiroshima, and the Atlantean Amir was killed by the supervillain Shogun. Intelligence agent Charlemagne tricked Spider-Man, of all people, to kill her to avoid being captured by the Russians. Over on Earth-807128, Maureen Logan (née Bouchard) died during an attack by the Hulk Gang, kicking off Old Man Logan's quest for revenge.
There may or may not be more tragic Wolverine-adjacent deaths out there. For instance, the Earth-982 Logan was married to Elektra, which couldn't have been good for her long-term survival, though we don't know for sure what came of her. Nevertheless, the aforementioned eight women all had a place in Logan's heart before their untimely deaths.
Two love interests stand above the rest in Wolverine's life
Though each of the aforementioned lovers have been important in Wolverine's life, two stand out. Jean Grey is an original X-Men member, and the love triangle between her, Cyclops, and Wolverine might be Logan's most prominent romantic entanglement in the comics. Though the untold truth of the Dark Phoenix is considerably more convoluted than the original Phoenix Saga, this famous story ends with Jean's death on the Moon. Like some others mentioned here, Jean does eventually get better, but hey — it's the comics, so where would we be if character deaths didn't count?
Less cosmic but still extremely tragic is Logan's relationship with Mariko Yashida, a prominent member of the Japanese Yashida clan. Mariko debuted in 1979 and soon became Wolverine's primary romantic interest, but their happiness tended to be fleeting. Clan interests, mind control, and other factors undermined the relationship, and Wolverine ultimately has to mercy kill Mariko after an assassin poisons her with a painful toxin. Like Jean, Mariko returns later, and there are various alternate-universe versions of her running around. Even so, the tragedies surrounding Mariko make her a prime example of Wolverine's bad luck with love.
Wolverine's tragic dating life explains some of his signature grumpiness. Still, at least Logan can find small consolation in the fact that fellow sulker Batman has experienced nearly the same amount of heartache in a fraction of time.