After some less than cheerful breakups (and the occasional psychotic phone call from a disgruntled ex) it was time for The Miss to find someone who could reveal why breaking up is so hard to do. Turns out all we needed was a guy. Dating expert and author Evan Marc Katz sat down to break up with us—the nice way.

SM: Can a breakup be amicable?
Evan: Absolutely. There are a lot of people who feel that there’s some sort of game to dating, that if one person wins then the other person loses. It’s not about that. If two people realize that they’re not meant to spend the rest of their lives together, it doesn’t mean that everything is bad or that the entire relationship is irredeemable. It means that maybe 90% is right and 10% is wrong and you can’t overcome that 10%. So you part with love and wish the person the best. And when you have that distance, you maintain that person in your life as a friend. I’m friends with a bunch of women I’ve dated.

SM: Really?
Evan: My poor girlfriend has met half of them.

SM: I’ve been broken up with in pretty crummy ways. Don’t I have a right to hate my exes?
Evan: OK, if your boyfriend was a prick, then yes, you can hate him. You have every right to hate him if he did something wrong. But if you have a loving relationship and it doesn’t work, I don’t see any reason for hatred to come into the picture as much as sad acceptance. We gave it a good run. And we built up so much together, and we meant so much to each other, do we have to throw this all out? What’s the best way to proceed so we can both be healthy and happy?