This is a movie about a guy heart broke over a JOB not a woman.
To me this movie is about a guy who is not all he can be because he's working a job he hates.
Then he meets this woman and the thought of having a girlfriend is enough to make it through the next day.
BUT because he's unhappy with his job, it's holding him back in all areas, including the kind of partner he's expecting to have.
So he meets this chick summer. At first he's sort of 'faking' the connection and chemistry and summer is actually more attracted to his friend who is not appropriate to date. but how are you going to even get excited about dating or entering a relationship not knowing the person unless you try and fake it at first until hopefully something real develops...
Then you look at the relationship he had with summer. He's dead inside because of his job, thinking this is his only contribution to society when he expected more, and in a lot of ways he's dead to the relationship. He remembers the high notes, out of those 500 days, like the two or three days where she just made a real funny joke or lit him up but even when he's with her, he would rather reminisce than be with her.
She's getting confused. Like he loves her too much for her to just leave him but is this love real? is it because of her looks or some funny joke she made one day or something relatively trivial that makes him ignore the rest of her? but she stays with him for too long just hoping for more...
Then they break up... He's still in the same job that he hates and he can't deal with it... but if he thinks of that he's over forever. So starts thinking of the relationship as an unhealthy coping mechanism to avoid thinking of other problems which are primarily job related...
He meets her one day. She looks at him with a mixture of pity and pain... She's still hurt because she feels he never saw the real her and that causes some doubt in her as to her worth, and she still sees that he's still hurt... so she leads him on, he goes to her house, finds out she is engaged and gets chewed up... but what she's doing is not just mean... it's a mixture of revenge for not being appreciated **for her** the real person and this idea, this guy's been hurting for too long use him up quick so he can recover...
And then after he goes through that torture, towards the end of the movie, we see him finally trying to make a recovery.... he's looking for a new job... he meets a woman and there's some chemistry and he's interested in dating again. But why? Because he has hope for his career. Without that he could never recover because that was the real problem. Summer was just a distraction tool, and that's why she's so pissed off... she can't put her finger on it (at least not conclusively) but she knows he wasn't 'with her' in the present moment when they were dating, and that's really hurtful too, just an unintentional pain..