Am I Beautiful?

From Ugly Duckling to Firebird

An Ask E. Jean Classic

Dear E. Jean: 

Most of my life I've been unattractive. My family has always assumed I'll never find a man, and during college it was not unusual to overhear unkind words in regards to my looks. But two years ago I lived in Italy, and I learned to put myself together—how to style my red, curly hair, what to wear, and how to walk. I'm petite and have a great body (I was a national level athlete). In short, I would not pass for beautiful, but I'm interesting and appealing.

Now I'm 30, back in the states, I have a good job, friends I cherish, and an active social life. But I'm still taken aback when men look at me. Friends have to tell me men are looking—I'm usually sure they're looking at the person behind me. This year I went out with a great guy—smart, made me laugh, very handsome—though we weren't well-suited as a couple. We broke up partly because I was insecure about his interest in me.

On a conscious level I realize there are more possibilities open to me than I …