(But Sometimes I Can Leave Stuff Out)

Dear Breakup Girl,

I can’t figure out how to tell my boyfriend I want to break up without hurting his feelings. He has really bad breath, aggravates me about if I like him or not (which I did until he annoyed me with the question too much), and he wears makeup to cover acne (he thinks I can’t tell, I guess). What to do?

— Darlene

Dear Darlene,

The lesson in your letter for all of us is that two things do not work: (1) bugging someone about whether they like you or not, and (2) tinted Clearasil. In fact, they both backfire.

But more to your point. IMPORTANT BREAKUP GIRL MAXIM: There is no such thing as “breaking up with someone without hurting his/her feelings.” Are you kidding me? I mean, come on. Our pride gets a little rug-burned even when people we don’t like don’t like us, never mind the people we do like.

So tell him nicely but firmly that it’s just not a happening thing any more. Even if he presses for details — which he will — don’t you dare mention the breath. Or the makeup. Those are things that a well-intentioned close friend or tactless aunt — not an about-to-be-ex-girlfriend — should let him in on. You can’t not hurt his feelings, but you can spare a few of them.

Love,
Breakup Girl

Originally published February 9, 1998