Part One: When something bad happens to your friend, don’t try to cheer him up with clichés. In fact, don’t try to cheer him up at all, especially immediately after the bad thing happened.
So what should you say? Here are some acceptable options:
-“I’m sorry.”
-“That sucks.”
-“That sucks. I know what that’s like, and it sucks.”
-“That sucks. I can’t imagine what that’s like.”
Infinitely better, each one.
If you want, you can throw in, “Let me know if there’s anything I can do,” but nothing more. Your friend will let you know when he’s ready to be cheered up.
Part Two: If you’ve been seeing somebody for a while and you're ready end things with them, don’t do it by email.
Part Three: If somebody says that something bad happened to them, and then he clearly implies what the bad thing is, it should be clear that he wants to note the bad thing, but not discuss it. So even though he's kind of baiting you, given that he's going through a rough time, why not indulge him?
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