SM: But someone always has to be the bad guy. Someone has to bring it up. How do you do that without being hated?
Evan: The question is: How would you like for someone to do it to you? It’s not much more complex than that. There’s no one answer, but I suggest that if you’re ever thinking of breaking up, think: “How would I want someone to break up with me and what’s the most painless way it’s going to happen?” Well, it’s certainly face-to-face. It doesn’t have a time limit. It’s not before you run to work. And you don’t place blame. It’s not, “You’ve done this wrong,” because that implies that they can do something different to get you back.

SM: It’s hard to get back together after a breakup like that.
Evan: Well, it’s a breakup. You told someone that something is broken.

SM: What about people who get back together after they breakup?
Evan: A lot of the time they get back together out of loneliness and need. And you might get a little panicky because dating itself is difficult. And sometimes it’s not fun, sometimes it’s frustrating. So there’s a reason that people scramble to get back together, but it doesn’t fix what was broken before. So I’m not going to say that you can’t get back together, but things don’t change because you’ve broken up. Those problems are still going to exist.

SM: Well, what about when you breakup, and then stuff happens with other people, and you get back together. What should you do about the time in between?
Evan: Don’t ask, don’t tell.