Didn't she break up with him because she had feelings for someone else? That may have been the bit that was glimpsed in her diary. I think people guessed that someone was her former skeezy photographer Dean. Ben was absolutely a tool, one of those overly confident bros who thinks he needs to grace the world with his cleverness and jock face. Anytime he appeared in her vlogs, I had to fast forward. To his credit though, he did seem really into her.