In the second and third seasons of the 60s cartoon he bounced between crushes, and one of the episodes ended with him being crushed that a crush of his hated his cowardly guts, and the episode closing quote "She's a girl, there are more of those".
In the 90s cartoon he kept avoiding meeting MJ, once he did it was after Felicia warmed up to the idea of dating him, but then she got mad at him for ditching her during the Spider-Slayer attack on Jameson's penthouse and didn't want to see him again, then Peter started dating MJ, and after she got past her physics test Peter jumped at the possibility of dating Felicia again.
In season 2 of the same show he learns that he's mutating, and that's why he wanted to date MJ, then he decided to ignore her cause he's mutating after she agreed to date him.
He kisses Lady Vermin in Unlimited.
He looks through his room window to see MJ in her room in the first Raimi film, what if she was indecent? Weirdo. And then he tries to swipe her away from any other guy dating her, especially his best bud.
In the MTV show, Peter bounces between two girls so much that an illusion in the series finale made him choose between the girl he had a crush on since she moved in next door, or the girl he choked and dropped to a lower roof of a warehouse.
Back to the movies, first movie ends with him telling MJ he can't date her, and he will always be her friend while breaking her heart in the funeral of her boyfriend's father (he's not such a nice friend, is he), and then he tries to sweep her away after learning she dates and promised to marry his boss's son. She's not a nice person either.
And when they are finally dating, he never lets her finish her sentence, that's why she went to his amnesiac best friend to talk to him, at least he will listen. They both regretted that kiss they exchanged instantly, I'm not gonna hate MJ in Spider-Man 3.
Back to animation, and Peter dates Liz Allan, and then annoyingly is rude to her while looking at the girlfriend of his best bud, and then both Peter and Gwen plan together that they will break up with their dates to date each other. Peter in Spectacular in not just a jerk to Liz, he's a jerk to his buds as well. Flash Thompson was right in calling him out in the hospital.
And then he keeps taking pictures of Gwen without her permission in Amazing Spider-Man, and then he bounces between wanting to see her and respecting her father's dying wish of keeping her out of his adventures, which he does by staying away from her. Her death was caused by her choice, but he was still not nice.
I'm pleased they chose to not make him date in the newer Disney cartoons, a lot of drama and dickery avoided there. He's not that rude in comics, why is he poorly adapted like that so often?