Dear Cary,
Last fall I broke up with my boyfriend of three years (we were close friends for two prior years). The decision to end our relationship was a hard one, fraught with all the classic self-doubt and dread, but in the end we had grown apart too much and lived apart too long for me to keep pretending that I still loved him. Somewhere we turned into two nice people who had occasional mediocre sex.
Even if I couldn't convince myself that things were fine, he believed it and had no idea what was coming. I tried to make the breakup as easy as possible for him, calling three of our mutual friends to make sure that they would be available to provide emotional support, and I planned to have the talk at his house when he didn't have any meetings or a need to drive for the rest of the day. Once there, he asked questions and I answered. He cried and I held his hand. Leaving, I promised to call him in a week and check how he was doing.
Since then we've made strong efforts to "stay friends" -- regularly talking on the phone and seeing each other at the occasional party. He is aware that I've started going out with other guys again. However, he is still trying to convince me that separating was a mistake and we should get back together.
This is my first formal breakup and I'm trying to learn how to do it the right way. How can I find the balance between politely refusing his advances and being cruel? Deal with the guilt of cutting him deeply and letting him waste his teenage years? Support him as a friend without leading him on?
Dirty Handed
Dear Dirty Handed,
You've handled all this with so much delicacy that at this point it's not more sensitivity you need, but a little toughness. If you don't want to be cruel, you must be firm. Too much kindness may be giving him the wrong idea. You've got to be sure that you don't give him any reason to believe that he's got a chance. So be tough. In everything you do -- your tone, your manner, your choice of greetings, where you see him, how long you talk -- you've got to convey a consistent message: The romance is gone and it's not coming back.
Believe me, the sooner he stops hoping you'll change your mind, the sooner he can start getting over it. That also means stopping your attempts to "support him as a friend." What he needs is distance from you, and certainty that it's really over. You've done a marvelous job so far. I think it may be hard for you to accept that this is the next phase, but once you do it, you'll see that it's not really cruel. It's just adult.
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