Sometimes. Hubris is certainly one of the easiest flaws to take advantage of.

[That's how they got Bill, after all. It's also kind of a heavy statement even in a fairly-innocuous context so instead of following up on that thought he downs the rest of his Paloma. He also makes no move to immediately order a second drink. Food, maybe? He'll think about it.]

Unless it's unicorns. Don't even bother with unicorns. It will never be worth it.