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As the old saying goes, "love can drive you crazy." In the case of Debra Whitman, that may well be a very literal statement. Introduced way back in 1979, Debra was a secretary in the biophysics department of Empire State University where Peter Parker went to college. The two began dating, but the relationship could never really progress because Peter would often miss dates to go off and save the city as Spider-Man.

Debra went on to get married to an abusive man, which brought out her mental instability. Debra convinced herself that Peter was Spider-Man, and while she was right, no one believed her. In an attempt to help get Debra the psychiatric help she needed, Peter admitted to her that he was Spider-Man. Debra instantly realized just how crazy that sounded and got the help she needed.

A crime scene investigator and one-time friend of Gwen Stacy, Carlie Cooper and Peter started dating shortly after the events of One More Day. As usual, Peter's life as Spider-Man kept getting in the way of his relationship with Carlie.

After being turned into a spider monster by the Jackal, Carlie comes to the conclusion that Peter really is Spider-Man. Angered by Peter's deception, Carlie ended their relationship. When Doctor Octopus took over Peter's body and became the Superior Spider-Man, Carlie was one of the first person to realize that something was weird.

Priscilla "Cissy" Ironwood is a comic book oddity. Readers have never seen how she and Peter met; the first mention of Cissy is in Marvel Team-Up #79 when Peter says he's late to a party because he was on a date with her. She makes her real debut in the next issue when she and Peter are attacked by a werewolf.

When Cissy's father, Dr. Daniel Ironwood, invented an anti-matter bomb, the Soviet Super-Soldiers wanted to get their hands on it. Spider-Man and Hulk were able to stop the soldiers, but Dr. Ironwood died in the battle. After her father's death, Cissy left New York and returned home to Montana.

High school crushes can be tough, and when it's the kind of crush Peter had on Liz Allan, it can leave a mark well into adulthood. A fellow student at Midtown High School, Liz Allan was one of the cool kids. She was smart, pretty, and was dating the school's resident hunk, Flash Thompson. To Liz, the four-eyed geek who weighed 90 pounds soaking wet wasn't someone she thought about often, and when she did think about him, her thoughts began and ended with "what a loser."

Liz's feelings changed when Peter started dating her best friend Betty Brant, but by then the Parker ship had sailed. Peter and Liz would become close friends, but romance was out of the equation. Still, unrealized love is one that can be felt for a long time.

In the Ultimate Universe, Peter and Kitty Pryde were both roughly the same age. Being two teenaged superheroes, they ended up having a lot in common and started dating. The two became the "It" couple that everyone loved to talk about, but Peter knew that the person his heart really wanted was Mary Jane. After a while, the excitement of dating a fellow superhero faded away, and Peter and Kitty realized that they weren't meant to be. Kitty went back to hanging with the X-Men, and Peter rekindled his relationship with Mary Jane.

A high school drop out, Betty Brant was working as J. Jonah Jameson's secretary at the Daily Bugle when she met Peter. Betty was the first woman Peter ever dated, and adding to the uncomfortableness of being in his first relationship, Betty blamed Spider-Man for her brother's death.

The two only dated for a short time, but your first relationship always holds a special place in your heart, and in this case, Peter seems to be forever connected to Betty. Years later they would hook up again, despite Betty being married. Oh, and her husband was Ned Leeds, who was brainwashed into becoming the Hobgoblin before being murdered in Berlin.

If it wasn't for a whole thing that happened on a bridge that we'll be getting to in a bit, the romance of Spider-Man and Anna Maria Marconi would be the most tragic. After taking over the body of Peter Parker and learning why the genius sacrificed so much to be a hero, Doctor Octopus decided to give up his evil ways and become the "Superior Spider-Man."

The two met when Otto/Peter decided to re-enroll at Empire State University to finally get his doctorate. Anna Maria was a student there and the two soon began to date. Anna Maria was a sign that Otto had truly changed when he became Peter Parker. He found love and acceptance in Anna Maria, and her belief in him drove him to be a better man. When Norman Osborn captured Anna Maria, Otto gave up control of Peter's body to save her. Anna Maria learned the truth and the romance between the two ended.

When it comes to dating a bad girl, Peter hit the jackpot with Felicia Hardy, the Black Cat. Black Cat started her career off as a criminal but was soon persuaded to become a hero thanks to her attraction to Spider-Man. For a time, Peter found himself trapped in a romantic triangle as he dated Felicia and Mary Jane. In the end, Peter chose the redhead next door over the girl in tight leather, but he still finds himself physically attracted to Black Cat, and he really didn't like it when Felicia and Daredevil kissed once.

Mary Jane Watson is the kind of person we all hope to fall in love with. She's smart, beautiful, tough, courageous, and funny. The woman wasn't kidding when she told Peter "Face it, tiger, you just hit the jackpot." Set up by their aunts, Peter and Mary Jane have had one of the more memorable relationships in comics. They dated, fell in love, got married, had a child who they were told died in birth but was really stolen by Norman Osborn and never seen again, had their marriage - and their love - erased from history by Mephisto, and fell in love again.

These days, Peter and Mary Jane are dating again, and they are very much in love. If Peter has his way, they'll get married sooner or later, but the people behind the keyboards who control Peter's life may well have other things planned. After all, a happy Spider-Man is a story we rarely see.

Mary Jane may be the woman Peter Parker married, but that's only because his first true love died in one of the most tragic stories ever told in comics. Gwen Stacy, in her short skirts and knee-high boots, was the object of desire for just about every man that saw her, but her heart belonged to Peter. That love would end up getting her killed.

Green Goblin took Gwen prisoner and brought her to the top of either the Brooklyn Bridge or the George Washington Bridge - a debate that will never be settled - and then tossed her off the side when Spider-Man showed up. Moving quickly, Spider-Man shot a web that connected to Gwen's foot. It stopped the young woman from falling into the ocean below, but it also appeared to snap her neck, killing her. The death of Gwen Stacy would forever hang over Spider-Man with the same weight as the death of Uncle Ben.