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(#1) Black Cat
Felicia Hardy, AKA Black Cat, falls hard for "Spider" and vice versa, after Peter and Mary-Jane break up. They date seriously for a long time, being fun, spontaneous, and playful.
Eventually, after Mary-Jane takes a trip, Peter realizes how much he loves MJ. That plus the fact that Black Cat can't fully accept civilian Peter Parker is enough for them to call it quits. But they still banter and flirt constantly.
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(#2) Mary Jane Watson
Mary-Jane Watson, the girl next door. Literally. Aunt May's best friend, Anna Watson, tried to set that nice, young boy, Peter, up with her niece for months, but he kept dodging her. Eventually, he couldn't escape any longer, and he meets the stunning party girl.
Pete ends up dating Gwen Stacy, but that never stops MJ from flirting. After Gwen's untimely end, she matures, begins taking care of Peter, getting him through the loss of his uncle, and they develop strong feelings for each other.
He reveals his secret, which she admits to knowing for some time, and proposes - many times. Eventually, she agrees and they wed! And live mostly happily ever after, until silly continuity and storylines ruin everything.
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(#3) Gwen Stacy
- The Amazing Spider-Man
Peter Parker's first true love. The One. Gwen Stacy is struck by Peter's brains (and later brawn). After getting over his infatuation with Betty, Pete falls hard for her, and they begin seriously dating. The word marriage is tossed around, and the two couldn't be more in love.
Then Green Goblin tosses Gwen off the Brooklyn Bridge, and Spider-Man catches her by a web, accidentally snapping her neck. This moment haunts Peter to this day.
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(#6) Silver Sable
In regular continuity, there's always a certain underlying tension between Spider-Man and Silver Sable.
It goes even further in a "What-If?" issue wherein Spidey had been married to the Black Cat before she's slain by Paladin. It starts with them reminiscing and sharing one another's grief, but eventually, Silver Sable and Spider-Man end up together.
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(#8) Betty Brant
Betty Brant is Peter Parker's first quasi girlfriend. She's also J. Jonah Jameson's secretary at The Daily Bugle. The two date off and on for a few months, but Peter's constant disappearance, her hatred of Spider-Man, and her shady past (family stuff) all begin to take a toll on the relationship.
She eventually dates and marries fellow Bugle employee Ned Leeds.
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(#9) Liz Allen
The one that got away. The hot girl everyone pines after, who was constantly dating the jock, Flash Thompson, in high school. Young bookworm Peter Parker vies for, and eventually gets, her attention, but things fall apart when he misses date after date as Spider-Man.
She eventually marries and has a child with Pete's best friend, Harry Osborn.
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(#11) Carlie Cooper
Carlie Cooper is an NYPD detective who's friends with Lily Hollister (Norman Osborn's new girlfriend). The two meet through Norman and Flash and immediately hit it off. They begin dating quickly and seem perfectly happy together. Her connection to and information from the police prove invaluable to Spider-Man.
Unfortunately, she quickly figures out he IS Spider-Man and breaks off the whole thing, leaving New York altogether.
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(#12) Sophia Sanduval
Sophia "Chat" Sanduval is a character exclusive to the Marvel Adventures: Spider-Man continuity. She's Emma Frost's best friend, who is one of the few who know that Peter Parker is in fact Spider-Man. They develop deep feelings for one another and begin dating, even though in this universe, Emma is into Spidey too.
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(#13) Michelle Gonzales
One of those strong love/hate relationships, Michelle Gonzales is the sister of (post "Brand-New-Day" continuity) Pete's roommate, Vin Gonzales. They immediately hate each other, but when Vin is arrested, she's forced to move in. Pete gets kidnapped and is replaced by The Chameleon (it's a whole thing), who woos Michelle. When the real Peter returns, they're a bit of an item.
Things are constantly rocky and intense, and she eventually returns to Chicago upon Vin's release from prison.
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(#16) Anna Maria Marconi
Anna Maria meets Peter as a student as Empire State University. The two hit it off and started dating. They start living together, and the relationship gets so serious that Anna Maria finds an engagement ring hidden in their apartment.
Unfortunately she soon figures out that Peter is Spider-Man, and then that Peter/Spidey is mind-swapped with the villainous Doc Ock.
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(#17) Debra Whitman
Whitman is an Empire State University student Peter meets (she's also yet another secretary) and falls for. They date on and off for months, but Pete's frequent absences stress the relationship.
She begins to develop schizophrenia (ironically set off by her belief that Peter Parker is Spider-Man) and eventually leaves New York with another man.
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