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female
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anonymous
writes: I'm too nervous to break up. Though I'm pretty sure it's not working on my side (I find him too soft, too much of a pushover; I often worry he won't stand up for himself if he needs to, or that I may accidentally hurt his feelings being too honest and him not tell me about it and just sit and sulk), I still don't want to hurt him. He's extremely nice and sensitive, if a little shy (doesn't have many friends), and I'm by nature what you'd call "brutally honest".Though we're pretty similar in other ways all around, this one difference seems to be very much annoying to me, and has gotten more so in the relationship (it isn't that he's gotten softer, really, but rather that I notice it more and it bothers me more). On top of this, I seem to have lost interest in him, and doubt my feelings about him quite a bit. This tells me I ought to break up with him, but I can't get my nerve up to do it. We're best friends as well as dating, and I want to be able to walk away with our underlying friendship still intact. Sort of like a delicate surgery to remove the "dating relationship" layer that's become diseased, but leave the healthy friendship.Does anyone know a way to break it as gently as possible? I do care about him as a friend, but I just can't see us together any more, and I can't get my guts together to tell him.
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female
reader, anonymous, writes (16 January 2006): the only way for this to work is if he's ready for the relationship to end as well. when you break your best friend's heart, the friendship is never the same. that's just the unfortunate part of dating; i've never managed to stay friends with a guy after breaking his heart, even when the friendship pre-dated the relationship by 13 years.
that doesn't mean you shouldn't break it off. it might break his heart, but it sounds like that would be the best thing that could happen here. the relationship isn't for you, and you shouldn't stay in it out of guilt.
tell him gently, but firmly, that you care about him very much but don't see a romantic future together. tell him you'd love to retain the friendship that you value so much, but don't hold your breath on it - my guess is, he won't be able to do it.
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