Recounting tales, especially of boys with The Bestfriend (clearly, I fail the Bechdel test), usually begins and ends with her saying, "Anna, don't read too much into this."
But being an over-zealous Psychology Major, I think I get a hall pass when it comes to overthinking it. And when I say overthink, I mean, being borderline obsessed. Overthinking 99% of the time isn't a bad thing. Trying to read the signs and analyzing every outcome is in our nature. As social beings, we are predisposed, to try to make sense of our surroundings. Out of the information we gather, we're inclined to make positive assessments; assessments that are usually in our favour.
But when your assessment is wrong. When you realize a boy can bring you coffee everyday for two months or beseech you to accompany him to a party, or flirt incessantly, without the ulterior motive that he likes you. When the question you keep asking yourself —so was it all in my head— becomes rhetorical. That is the 1% of the time when overthinking can suck some serious ass.
Segue, I think there's a reason why we like to consider men as elusive xy-chromosome carrying enigmas of the mystical. It's because if we don't, they'd just be simple one-dimensional cardboard characters. There'd be no mystery behind their every action, nothing to rant mindlessly about with The Bestfriend— nothing to overthink.