Dear Harlan: I recently got together with my ex. I broke up with him after we dated for a year. It was kind of messy and he had a hard time getting over it. Well, jump ahead to the holidays and we reconnected. I reached out to him and we got back together. We have been dating again for a couple of months and I’m starting to think I made a mistake. I feel terrible. I don’t want to hurt him again, but I can’t pretend like this is working. I know he will be devastated. Is there any way I can soften the blow and not make this hurt?
— Breaking Up Again
Dear Breaking Up: It’s going to hurt. He might cry. He might hate you. That’s part of it. Give him the respect and space to have whatever reaction he needs to have. If your intentions were genuine and continue to be genuine, that’s all you can communicate. The mistake would be cheating, lying or betraying him. The respectable and kind thing to do would be to explain your feelings. I know this isn’t what you wanted, but the longer you pretend and date him the less time he has to be with someone who will truly appreciate what he has to offer.