Before you become freaked out or offended by something your guy opens up to you about, maybe you should be honored: there are some things a man will only tell a woman he is extremely comfortable with.
Times he could have worked harder
Every man has some missed opportunities in his lifetime—times he could have proven himself at work, or times when, if he’d just worked a little harder, he could have become CEO or partner in a company. But instead, because he was young and didn’t understand what mattered in life yet, he was lazy, missed the opportunity of a lifetime, and has ever since regretted it. If he tells you that, he trusts you never to judge him.