TL;DR. The massive length here is setting off my troll alarm bells. I've described my entire senior year in high school in a fraction of the space.
If this isn't a work of science fiction my advice is that you never "break up" with female friends, esp. those you've been intimate with. First, when you've been with a woman the door usually stays open and you never know when you might feel the urge to go back in. Second, women have female friends and that's how you meet women. When you're 35 and not in school and women are harder to come by, then you'll appreciate your female friends more.
The only way I'd say dump a female friend is if she's creating such drama she's screwing up you life or if she's done something heinous, like stolen money from you or wrecked your car.
If this isn't a work of science fiction my advice is that you never "break up" with female friends, esp. those you've been intimate with. First, when you've been with a woman the door usually stays open and you never know when you might feel the urge to go back in. Second, women have female friends and that's how you meet women. When you're 35 and not in school and women are harder to come by, then you'll appreciate your female friends more.
The only way I'd say dump a female friend is if she's creating such drama she's screwing up you life or if she's done something heinous, like stolen money from you or wrecked your car.