#28: Brutal Honesty
People don't always want to face the truth; sometimes, they'd rather be deceived and live in an illusion, especially when the truth might be painful. However, in this case, the guy opted for brutal honesty, which turned out surprisingly well.
At the night's end, his date thanked him for dinner and a movie, to which he responded, "Yeah, I didn't have anything better to do." While such a comment might put some off, this girl found it hilarious. Fast forward three years, and they're happily married!