In his days at high school Peter was with Gwen Stacy. They had a great relationship since they were best friends as kids along with MJ and Harry. While it was a bit rocky after the death of George Stacy who got crushed by falling debris in order to save a kid (when Spider-Man and Doc Ock were fighting) things were going great
But Green Goblin (or his clone) figured out Spidey's secret identity and kidnapped Gwen Stacy. In an attempted to save her Spidey snaps Gwen's neck by accident killing her. He nearly killed the Goblin out of revenge but instead Green Goblin's clone died by his own glider
While it left Peter grieving for quite some time he eventually found love again with Mary Jane Watson
These next 2 are girls Peter didn't get together with but is still close with them
Felicia Hardy AKA Black Cat has had quite the history with Spider-Man but Spidey isn't interested in a relationship with her. Even when Black Cat found out who Spidey was, she loved Spider-Man and not Peter Parker
She dose flirt with Spidey on the occasional team up and Peter is having none of it. Felicia even said to Peter that his black suit was "hotter" than his classic suitCindy Moon aka Silk was bitten by the same spider that bit Peter. This means both have a special connection with each other and they still keep in contact
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My Spider-Man Headcanons
RandomThis is my take on everyone's favourite web slinger and his friends and foes in my very own version of earth 616. Also included are the many alternate timelines in the Marvel multiverse