Random Girlfriends of Peter Parker / Spider-Man (20 items)

(#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.
(#7) Rogue

In X-Men Forever continuity, Spider-Man helps Rogue develop and deal with her powers. He also tells her to follow her heart, which she does by trying to kiss him.
(#19) Marcy Kane

Mainly brought on as a polar opposite to the wild and free Black Cat (who was also introduced around the same time), the stuck up and snobby Marcy Kane doesn't last too long.
(#15) Jean Dewolff

In a situation that never turns into anything physical or requited, Spider-Man learns that police chief Jean Dewolff has had a longtime thing for the web slinger. Unfortunately, she's slain by the Sin Eater when Spidey leaps out of the way of a shotgun blast.
(#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.
(#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.