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Dear Breakup Girl,

I have a very interesting situation. My best friend and I are the same age (29). We even went to the same high school and lived in the same neighbourhood. We have been friends for almost ten years.

So here is the situation. I have dated several guys/men and even had some serious relationships. Two I actually lived with. Meanwhile there is my best friend going along with all these experiences that I have had in life. She has never had a boyfriend, she has never been kissed.

I always feel bad when I have met someone new and I want to share it with her. I always wonder if she is beating herself up because I can find someone and she can't. I hurt her quite badly this spring. I met someone and I didn't want to tell her because I thought it would hurt her feelings that I met someone again and she is still single.

Now I don't want you to think that I am berating myself but neither one of us are raving beauties but we are very attractive in our own ways and I think my best friend is very attractive. She has a stunning smile and she is so funny and smart, God is she is smart!

I just don't know what to say anymore. I go through heartbreak after heartbreak and she is always there for me and still she has not found someone.

What do you think of this?

-- Pat

Dear Pat,

An excellent question from someone who is clearly an excellent friend. I think what you have to do is find a middle ground between telling her nothing -- which can come off as patronizing, and is I think what you're referring to in your third paragraph -- and telling her ... everything. When you find someone, do share; don't gush. And in case of heartbreak, let her be there to handle General Sadness, but hit up another friend to help you handle all the specific slings and arrows. Finally, make sure you're there for her. If she's feeling lonely and hopeless, don't say, "I totally know how you feel" -- she will not believe you -- just say, "I totally know" and whisk her off to a party with other smart, nice, people.

Love,
Breakup Girl

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