Despite his perennial bad luck, Spider-Man has had many love interests. Peter Parker gained his powers when he was a teenager and then had to figure out how to become a superhero at a young age. But he also had another predicament to escape from — he was a nerd, an outcast, and a self-professed wallflower. Once he gained powers, though, he slowly gained confidence and eventually ended up dating girls who never gave him a second look before.

Peter Parker’s love interests changed over his time in comics, with some who knew he was Spider-Man and some who never learned his secret identity. Sadly, most of his relationships ended badly since he had to put many of these girlfriends on the backburner while he fought crime, and only a select few would tolerate that. Spider-Man’s love interests have included other superheroes, models, students, criminals, and more, and with no exception, none of his romantic relationships were easy on him.

20 Jill Stacy

Spider-Man #76 by Howard Mackie, John Romita Jr, Scott Hanna, Richard Starkings, Liz Agraphiotis, and Comicraft

Spider-Man’s true first girlfriend was Gwen Stacy. She was also his greatest tragedy as she died in his arms when he was unable to save her. That made Peter Parker’s romantic relationship with Jill Stacy so awkward.

Jill Stacy was Gwen’s cousin. At first, Jill was there as a friend to Mary Jane, but eventually, she ended up getting close to Peter when he and MJ had some trouble. When Peter thought MJ died, he moved on to a relationship with Jill, but that all ended with Mary Jane turning out to still be alive.

19 Debra Whitman

Amazing Spider-Man #196 by Marv Wolfman, Al Milgrom, Jim Mooney, Frank Giacoia, Bob Sharen, and John Costanza

Out of all Spider-Man’s girlfriends, the one that remains the most disturbing was when he dated Debra Whitman. Peter met Debra when he was a teaching assistant at Empire State University, and she was a secretary. The two developed a relationship despite her being with an abusive husband.

She began to have delusions that Peter Parker was Spider-Man, and the worst part is that he lets her believe it. After this ends, she decides to divorce her husband and then leaves Spider-Man comics for years.

18 Captain Marvel

Ms. Marvel #47 by Brian Reed, Mike McKone, Rob DiSalvo, Derec Donovan, Chris Sotomayor, and Dave Sharpe

One of Spider-Man’s most surprising girlfriends is Carol Danvers. After several years of working as a lone hero, Spider-Man joined the Avengers and became an even stronger hero, with much more confidence. This is when Spider-Man dated Carol Danvers – Captain Marvel.

At the time that they dated, Carol was still going by the name Ms. Marvel, and Peter even revealed to her his secret identity. They didn’t get much further than dating, but it was clear that Carol really liked Spider-Man.

17 Anna Maria Marconi

Superior Spider-Man #5 by Dan Slott, Giuseppe Camuncoli, John Dell, Edgar Delgado, Antonio Fabela, and Chris Eliopoulos

Anna Maria Marconi was never a Peter Parker love interest, but she was Spider-Man’s girlfriend. This was when Doctor Octopus took over the body of Peter and became the Superior Spider-Man. It didn’t take long for Ock to become a hero himself, and this is when he fell for Anna.

Superior Spider-Man met Anna at Empire State University, and they fell in love. Ock was even going to propose to Anna and marry her, but that was all spoiled when Peter regained control and broke things off with her after that.

16 Lian Tang

Amazing Spider-Man #1 (2015) by Dan Slott, Giuseppe Camuncoli, Cam Smith, Marte Gracia, and Joe Caramagna

Lian Tang is a more recent girlfriend of Spider-Man. After Peter Parker regained control of his body, he helped raise Parker Industries into a powerhouse company, and he began working in Shanghai, where he started dating a scientific designer named Lian Tang.

Lian even created the Spider-Mobile for Spider-Man. This Peter Parker love interest eventually fell apart when he learned she was working for Zodiac, and even after forgiving her for the betrayal, their relationship could never recover.

15 Michelle Gonzalez

Amazing Spider-Man: Extra! #3 by Marc Guggenheim, Fabrizio Fiorentino, Pat Olliffe, Kris Justice, John Livesay, Serge LaPointe, Chris Chuckry, Allen Passalaqua, and Rus Wooton

One of the most hated of Spider-Man’s girlfriends ever has to be Michelle Gonzalez. After Mephisto erased Peter’s marriage to Mary Jane, he had a new life and ended up roommates with Vin Gonzalez, a police officer who was partner with Carlie Cooper.

Michelle was Vin’s sister and while she and Peter did not like each other at first, they started to date anyway. She then became extremely over-possessive of Peter until Chameleon showed up and came between them, causing more problems until Michelle finally left for Chicago.

14 Silk

Amazing Spider-Man #1 (2014) by Dan Slott, Humberto Ramos, Victor Olazaba, Edgar Delgado, and Chris Eliopoulos

A more recent girlfriend for Spider-Man came in 2014 when he started dating the superhero, Silk. This was one that fans loved for a short time, but it remains one that never really developed into anything strong. Cindy Moon had an origin tied to Peter Parker, both bit by the same radioactive spider at the same event.

What led them together was the spider venom that both received, which gave them an animalistic attraction to each other. The two ended up as allies and fought together, but they never tried to be anything more than a short-time passionate connection.

13 Mockingbird

Marvel Team-Up #95 by Steven Grant, Jim Janes, Bruce Patterson, Ben Sean, and John Costanza

Another one of Spider-Man’s surprising girlfriends, Mockingbird is best known as Hawkeye’s ex-wife. However, in 2017, Spider-Man and Mockingbird ended up in a relationship together. This was when Parker was the CEO of Parker Industries and worked with S.H.I.E.L.D. on different projects, which led him to spend time with Mockingbird.

Peter even created a new costume for Mockingbird and then the two ended up in a romantic relationship. This never matched up to most of Peter’s relationships though, and they eventually split when they realized they had nothing in common outside of working as superheroes.

12 Sarah Rushman

Spidey/Marrow #1 by Scott Lobdell, Ale Garza, Pierre-Andre Dery, Steve Buccellato, Richard Starkings, and Albert Deschesne

Sarah Rushman was one of the more ambiguous girlfriends that Peter Parker has had. She was a member of X-Force and the Brotherhood of Evil Mutants, and at one point she was forced to join S.H.I.E.L.D. against her will. While brainwashed by S.H.I.E.L.D., she posed as university student Sarah Rushman. She quickly developed a crush on her professor, Peter Parker, and the two even went on a few dates. After Sarah’s true identity was revealed, Peter was able to help her escape S.H.I.E.L.D. and, with her memories restored, Sarah was no longer interested in a romantic relationship with Peter.

11 Natasha Romanov

Marvel Team-Up #82 by Chris Claremont, Sal Buscema, Steve Leialoha, Ben Sean, and Rick Parker

Peter Parker has had tons of love interests over the years, but few are as dangerous as Black Widow. Natasha Romanov is one of the greatest secret agents in the Marvel Universe, which often makes her a major target for Hydra. Black Widow was captured and tortured by Hydra so extensively that her mind regressed to an alternate personality, so she wouldn’t give up information. This new personality was Nancy Rushman, a school teacher. When Spider-Man rescued her, she quickly developed romantic feelings for the web-slinger, but when her memories returned, she lost any romantic attraction to Peter, so nothing ever happened between the two.

10 Betty Brant

Amazing Spider-Man #4 (1963) by Stan Lee, Steve Ditko, and Sam Rosen

The first love interest of Peter Parker’s life came when he got his first job in high school as a reporter for the Daily Bugle. It was there that he met Betty Brant, the assistant to J. Jonah Jameson. The two noticed each other, even though Peter was younger than Betty. Despite this, they tried to date, making her perhaps Spider-Man’s first girlfriend.

The problems arose quickly when Peter had to keep disappearing and working as Spider-Man, fighting his first supervillains. Betty knew something was wrong and felt Peter didn’t like her. When Peter left one too many times, Betty told him she needed a break and ended up meeting and falling in love with Ned Leeds.

9 Silver Sable

Amazing Spider-Man #265 by Tom DeFalco, Ron Frenz, Josef Rubinstein, Bob Sharen, and Phil Felix.

One of Spider-Man’s most dangerous girlfriends was the assassin, Silver Sable. While Spider-Man dated heroes like Mockingbird and former villains like Black Cat, when it came to Silver Sable, she was a mercenary and went against everything Spider-Man stood for. And at first, they were on different sides of the law.

Silver Sable represented her own company and eventually teamed up with Spider-Man when her targets were villains. By the time Doctor Octopus tried to destroy the Earth in Ends of the Earth, Sable revealed her true feelings for Spider-Man, and sacrificed her life to save him.

8 Emma Frost

Marvel Adventures Spider-Man #53 by Paul Tobin, Matteo Lolli, Christian Vecchia, Guru-eFX, and Dave Sharpe

Emma Frost is one of the most powerful telepaths in the Marvel Universe, and she’s often gravitated around X-Men, with one of her most notable love interests being Scott Summers. But on Earth-20051, a young Emma Frost has a crush on Spider-Man. Emma reads Spider-Man’s mind and is shocked by the pure heroism and kindness inside Peter’s mind. Because of this, she instantly falls for the young wall-crawler and tries to get between him and his then-girlfriend, Sophia “Chat” Sanduval. This didn’t work out, and Emma eventually turned herself into the police to repent.

7 Jessica Jones

The New Avengers #51 by Brian Michael Bendis, Chris Bachalo, Billy Tan, Tim Townsend, Matt Banning, Antonio Fabela, Justin Ponsor, Richard Starkings, and Albert Deschesne

Another major hero in the Marvel Universe is that of Jessica Jones, a woman with major super strength. Her surprising connection to Peter Parker was revealed in The New Avengers #51, where she confessed that she had been in the same science class as Peter Parker in high school, even being on the same field trip when he got bit. Jessica also confessed that she had a major crush on Peter, but before she could confess her feelings, she had her own major accident that changed her life, as it resulted in her getting super powers, which meant boys were far from the most important thing on her mind.

6 Sophia Sanduval

Marvel Adventures Spider-Man #53 by Paul Tobin, Matteo Lolli, Christian Vecchia, Guru-eFX, and Dave Sharpe

A major love interest for Peter Parker on Earth-20051, Sophia was a mutant who could communicate with animals. Eventually, she felt she needed more human interaction in her life, which resulted in her meeting Emma Frost. Emma would use her telepathy to rob rich citizens, and the two would often go on crime sprees together, much to Sophia’s dislike. These crime sprees eventually caught the attention of Spider-Man, and after learning his true identity through her telepathy, Emma sent Sophia to Peter’s school to learn more about him. What Emma didn’t expect though, was Sophia becoming Spider-Man’s girlfriend due to this meeting.

5 Kitty Pryde

Ultimate Spider-Man Annual #1 by Brian Michael Bendis, Mark Brooks, Jamie Mendoza, Scott Hanna, Dave Steward, and Chris Eliopoulos

Perhaps the most surprising of Spider-Man’s girlfriends is the X-Men’s own Kitty Pryde. The Peter Parker and Kitty Pryde relationship only existed on the pages of Ultimate Marvel Comics. Kitty was a young teen member of the X-Men and Peter was a teenage superhero, still in high school. When Peter and Mary Jane broke up, he started dating Kitty.

This was a big relationship for Peter because it put him with a girl who was also a superhero, so they shared much more. Sadly, as great as this relationship was, and as much as Kitty really cared for Spider-Man, Peter could never stop thinking about Mary Jane, and that ruined things for them.

4 Carlie Cooper

Amazing Spider-Man #545 by J. Michael Straczynski, Joe Quesada, Danny Miki, Richard Isanove, Dean White, and Chris Eliopoulos

The main Spider-Man girlfriend after the Mephisto One More Day storyline erased his marriage to Mary Jane Watson was Carlie Cooper. Sadly, this relationship would never last because Peter hid his identity as Spider-Man from her, and she was a police officer.

The two met immediately after the Mephisto deal and Carlie started dating Peter after getting to know him better. Spider-Man destroyed their relationship and she broke up with him after discovering his identity in his popular comic book arc, Spider-Island, although they remained allies.

3 Black Cat

Amazing Spider-Man #194 by Marv Wolfman, Keith Pollard, Frank Giacoia, Ben Sean, and John Costanza

Most of Spider-Man’s girlfriends were people he knew as Peter Parker, but when it comes to Black Cat, it was the opposite. Black Cat started as one of Spider-Man’s villains and the two developed a flirtatious relationship during their battles that morphed into a romantic one, over time.

Black Cat was one of the few people besides Mary Jane Watson that had no problem with Peter operating as Spider-Man. The one thing that held them down was that she didn’t care about Peter at all. This changed over the years and currently Spider-Man and Black Cat are together again.

2 Gwen Stacy

Amazing Spider-Man #31 by Stan Lee, Steve Ditko, and Sam Rosen

One of Spider-Man’s greatest girlfriends was Gwen Stacy. While Peter Parker dated Betty Brant first, the first woman that he really loved was Gwen Stacy. She showed up for the first time in Amazing Spider-Man #31, but at that time, they were dating other people. Despite this, they gravitated toward each other and fell in love.

The two continued their relationship, and it grew into something important, and it seemed Peter had found the woman he would spend the rest of his life with. However, tragedy was waiting around the corner, ready to ruin Spider-Man’s life. Peter’s greatest villain, Green Goblin, killed Gwen in Amazing Spider-Man #121. The death of Gwen Stacy remains one of the greatest comic stories of all time, and for this reason Marvel has vowed to never resurrect Gwen, unfortunately for Peter.

1 Mary Jane Watson

Amazing Spider-Man #25 by Stan Lee, Steve Ditko, and Sam Rosen

The best love interest in Spider-Man’s life was the only woman who went on to become his wife. This was model Mary Jane Watson, someone who Peter knew was way out of his league, but someone who fell in love with him anyway. Their marriage was one of the best in Marvel Comics’ history.

However, they had to give up everything when Peter Parker made a deal with the demon Mephisto to save his Aunt May’s life. Mephisto erased their marriage and relationship from history. Despite this, their love was so strong and important that they found their way back to each other. Unfortunately, in recent stories, Marvel decided to end Peter and Mary Jane’s relationship again, which caused the indignation of Spider-Man‘s fans.